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(R)-2-乙酰氨基丙酸甲酯
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氨基酸及其衍生物
氨基酸衍生物
氨基酸及其衍生物

CAS号：19914-36-4

CAS号19914-36-4, 是氨基酸衍生物类化合物, 分子量为145.15, 分子式C6H11NO3, 标准纯度95%, 毕得医药(Bidepharm)提供19914-36-4批次质检（如NMR, HPLC, GC）等检测报告。

(R)-2-乙酰氨基丙酸甲酯 (请以英文为准,中文仅做参考)

(R)-Methyl 2-acetamidopropanoate , Ac-D-Ala-OMe

货号：BD111976 (R)-Methyl 2-acetamidopropanoate 标准纯度：, 95%
19914-36-4
19914-36-4
19914-36-4

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标准纯度包装价格上海深圳天津武汉成都VIP价格数量

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  • 产品信息
  • 结构/产品资料
  • 应用领域
产品名称 : (R)-Methyl 2-acetamidopropanoate , Ac-D-Ala-OMe
中文名称 : (R)-2-乙酰氨基丙酸甲酯(请以英文为准,中文仅做参考)
CAS号 : 19914-36-4
分子式 : C6H11NO3
线性分子式 : -
分子量 : 145.16
MDL NO : MFCD00080822
沸点 : -
Pubchem ID : 6951031
InChIKey : FQGVVDYNRHNTCK-SCSAIBSYSA-N

常用 :

SDS-BD111976

2D :

JSON XML ASN SDF

3D :

JSON XML ASN SDF
【用途一】

计算化学

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.67
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 35.24
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

55.4 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.75
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.57
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.32
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.16
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.11
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.12

Water Solubility

Log S (ESOL)?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.12
Solubility 111.0 mg/ml ; 0.764 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.12
Solubility 109.0 mg/ml ; 0.753 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.76
Solubility 25.4 mg/ml ; 0.175 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.59 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.67

合成路线：*资料仅供科研用途参考，更多细节请参阅原文出处。

  • 合成路线-上游产品

1~19  ►

1. 合成：19914-36-4

35356-70-8

19914-36-4
产率 合成条件 实验步骤
99% With ((R,R)-1,2-bis(tert-butylmethylphosphino)-4,5-(methylenedioxy)benzene)(1,5-cyclooctadiene)rhodium(1+)hexafluoroantimonate; hydrogen In methanol at 20℃; for 0.33 h; 通用方法：作为反应底物，438.5mg（2.00mmol）α-脱氢氨基酸2-（N-乙酰氨基）-3-苯基-2-丙酸 - 甲酸酯，和作为不对称氢化催化剂，1.55mg加入（2.RxR）-1,2-双（叔丁基甲基膦基）-4,5-（亚甲二氧基）苯）（1,5-环辛二烯）铑（1 +）六氟锑酸盐，氢气进行五次吹扫，并加入预先脱气的5mE脱水甲醇。随后，将氢气压力设定为3个大气压，然后开始反应。在室温下搅拌30分钟后，停止容器中的氢消耗，因此假定反应终止。在将反应液浓缩后，将剩余的白色晶体溶解在乙酸乙酯中，然后通过硅胶柱。当用HPLC分析所得洗脱液时，得到（R）-2-（N-乙酰氨基）-3-苯基丙酸甲酯，对映体过量（cc）为99.9％。另外，使用1 H NMR分析化合物，化学收率为99％或更高（表1中的No.1）。在这种情况下，HPLC条件如下：HPLC：Daicel Chiralcel OJ，1.0mE / mm，己烷：2-丙醇9：1j0085]每种对映体的保留时间（R）t = 13.3mm，（S）t2 = 19.3mmj0086]此外，不对称氢化反应在上述相同条件下进行，除了如表1所示改变反应基质和反应条件的类型，结果也示于表1中。
98% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
98% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
97% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
97% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
99.7 % ee With hydrogen In methanol at 25℃; （λ）-2-乙酰氨基丙酸甲酯，转化率100％，ee 99.7％（Chirasil Dex CB，25m×0.25mm，注射器/检测器200℃，氦气20psi，130℃，10分钟，然后以15℃/ min升温） 至200℃，保留时间5“2.91分钟，R 2.98分钟）。
96 % ee With 6-((1R,2S)-1-(diphenylphosphino)-3-methoxy-1-phenylprop-2-yloxy)dibenzo[d,f][1,3,2]dioxaphosphepine; hydrogen In tetrahydrofuran at -40℃; 实施例11.不同的不饱和烃化合物与手性配体2和[Rh（nbd）2] BF 4在-40℃下的不对称氢化下列化合物（a）在本发明催化剂存在下氢化（配体2和[Rh（nbd） ）2] BF4）在-40℃。
99 % ee With (11bP)-4-((1R,2S)-1-(diphenylphosphino)-3-methoxy-1-phenylprop-2-yloxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; hydrogen In tetrahydrofuran at 20℃; 实施例12.在室温下用手性配体6和[Rh（nbd）2] BF 4对不同的不饱和烃化合物进行不对称氢化。下列化合物在本发明催化剂（配体6和[Rh（nbd）2）存在下氢化 ] BF4）在室温下。
99 % ee With hydrogen In methanol for 0.50 h; [（R）-TriOCH2-ParaC Rh NBD]将BF4（2.2mg，0.002mmol）和乙酰氨基丙烯酸甲酯（286mg，2mmol）置于Endeavor Argonaut多孔压力反应器中的玻璃衬里中。 用氮气吹扫容器，加入脱气的MeOH（4mL）并用氢气将反应物加压至10巴。 将压力保持在10巴并监测氢气吸收。 30分钟后，释放压力并通过手性气相色谱分析反应（柱：Chirasil DEX-CB，方法：130℃10分钟，然后15℃/ min至200℃）：100％转化率，99 ％ee
85 - 90 % ee With hydrogen In dichloromethane; acetone at 20℃; for 0.0833333 - 0.25 h; 在玻璃高压釜中，将6.1mg（0.015mmol）[Rh（cod）2] BF 4溶解在15ml脱气的CH 2 Cl 2中，在氮气下加入0.016mmol配体和1mmol底物，并在室温下进行氢化。 1个大气压的氢气压力。 通过气相色谱测定转化率和ee。
> 99 % ee With hydrogen In methanol at 20℃; for 1 h; ; （实施例10至22）;在50mL高压釜中，6mg（1.0.x.10-2mmol）[铑（I）（（1S，1S'，2R，2R'） - 1,1'-叔丁基 - [2,2'] - 二磷杂环戊烷）（降冰片二烯）]在实施例8中合成并用作催化剂的六氟磷酸盐和1mmol表1中所示的脱氢氨基酸衍生物（或烯酰胺衍生物）。然后，将系统抽空并用氢气吹扫四次。将高压釜恢复至常压，打开旋塞，用注射器从旋塞中快速加入4mL脱气的脱水甲醇，然后关闭。用干冰/乙醇冷却反应器，然后将反应系统再次抽真空并用氢气吹扫四次。在氢气压力设定为预定值后，除去制冷剂，用磁力搅拌器搅拌反应体系直至停止氢气消耗。反应完成后，将反应溶液通过硅胶柱色谱（展开溶剂：乙酸乙酯）以除去催化剂，然后用蒸发器浓缩残余物，得到还原产物。在任何反应中，产率约为100％。用手性HPLC或手性GC分析每种产物的光学纯度（ee）。结果如表1所示。这些结果是以底物：催化剂= 100：1的比例得到的。[表1]

更多
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2. 合成：19914-36-4

35356-70-8

3619-02-1

19914-36-4
参考文献：
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3. 合成：19914-36-4

35356-70-8

3619-02-1

19914-36-4

N/A

N/A
参考文献：
[1] Journal of the American Chemical Society, 2002, vol. 124, # 23, p. 6649 - 6667

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生命科学 氨基酸及其衍生物 氨基酸及其衍生物

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1. 合成：19914-36-4

35356-70-8

19914-36-4
产率 合成条件 实验参考步骤
99% With ((R,R)-1,2-bis(tert-butylmethylphosphino)-4,5-(methylenedioxy)benzene)(1,5-cyclooctadiene)rhodium(1+)hexafluoroantimonate; hydrogen In methanol at 20℃; for 0.33 h; 通用方法：作为反应底物，438.5mg（2.00mmol）α-脱氢氨基酸2-（N-乙酰氨基）-3-苯基-2-丙酸 - 甲酸酯，和作为不对称氢化催化剂，1.55mg加入（2.RxR）-1,2-双（叔丁基甲基膦基）-4,5-（亚甲二氧基）苯）（1,5-环辛二烯）铑（1 +）六氟锑酸盐，氢气进行五次吹扫，并加入预先脱气的5mE脱水甲醇。随后，将氢气压力设定为3个大气压，然后开始反应。在室温下搅拌30分钟后，停止容器中的氢消耗，因此假定反应终止。在将反应液浓缩后，将剩余的白色晶体溶解在乙酸乙酯中，然后通过硅胶柱。当用HPLC分析所得洗脱液时，得到（R）-2-（N-乙酰氨基）-3-苯基丙酸甲酯，对映体过量（cc）为99.9％。另外，使用1 H NMR分析化合物，化学收率为99％或更高（表1中的No.1）。在这种情况下，HPLC条件如下：HPLC：Daicel Chiralcel OJ，1.0mE / mm，己烷：2-丙醇9：1j0085]每种对映体的保留时间（R）t = 13.3mm，（S）t2 = 19.3mmj0086]此外，不对称氢化反应在上述相同条件下进行，除了如表1所示改变反应基质和反应条件的类型，结果也示于表1中。
98% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
98% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
97% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
97% With hydrogen In methanol; toluene at 25℃; for 16 h; 铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化表2铑催化的α-乙酰氨基丙烯酸甲酯的不对称氢化Ex-Li-T [℃]，充足的溶剂t [h]％ee转化率10 1： 10 25,16 60 100 98（MeOH：甲苯）（R）11 3 1:10 25,16 61 100 98（MeOH：甲苯）（R）12 2 1:10 25,16 79 100 97（MeOH：甲苯） （R）13 4 1:10 25,16 7 100 97（MeOH：甲苯）（R）
99.7 % ee With hydrogen In methanol at 25℃; （λ）-2-乙酰氨基丙酸甲酯，转化率100％，ee 99.7％（Chirasil Dex CB，25m×0.25mm，注射器/检测器200℃，氦气20psi，130℃，10分钟，然后以15℃/ min升温） 至200℃，保留时间5“2.91分钟，R 2.98分钟）。
96 % ee With 6-((1R,2S)-1-(diphenylphosphino)-3-methoxy-1-phenylprop-2-yloxy)dibenzo[d,f][1,3,2]dioxaphosphepine; hydrogen In tetrahydrofuran at -40℃; 实施例11.不同的不饱和烃化合物与手性配体2和[Rh（nbd）2] BF 4在-40℃下的不对称氢化下列化合物（a）在本发明催化剂存在下氢化（配体2和[Rh（nbd） ）2] BF4）在-40℃。
99 % ee With (11bP)-4-((1R,2S)-1-(diphenylphosphino)-3-methoxy-1-phenylprop-2-yloxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; hydrogen In tetrahydrofuran at 20℃; 实施例12.在室温下用手性配体6和[Rh（nbd）2] BF 4对不同的不饱和烃化合物进行不对称氢化。下列化合物在本发明催化剂（配体6和[Rh（nbd）2）存在下氢化 ] BF4）在室温下。
99 % ee With hydrogen In methanol for 0.50 h; [（R）-TriOCH2-ParaC Rh NBD]将BF4（2.2mg，0.002mmol）和乙酰氨基丙烯酸甲酯（286mg，2mmol）置于Endeavor Argonaut多孔压力反应器中的玻璃衬里中。 用氮气吹扫容器，加入脱气的MeOH（4mL）并用氢气将反应物加压至10巴。 将压力保持在10巴并监测氢气吸收。 30分钟后，释放压力并通过手性气相色谱分析反应（柱：Chirasil DEX-CB，方法：130℃10分钟，然后15℃/ min至200℃）：100％转化率，99 ％ee
85 - 90 % ee With hydrogen In dichloromethane; acetone at 20℃; for 0.0833333 - 0.25 h; 在玻璃高压釜中，将6.1mg（0.015mmol）[Rh（cod）2] BF 4溶解在15ml脱气的CH 2 Cl 2中，在氮气下加入0.016mmol配体和1mmol底物，并在室温下进行氢化。 1个大气压的氢气压力。 通过气相色谱测定转化率和ee。
> 99 % ee With hydrogen In methanol at 20℃; for 1 h; ; （实施例10至22）;在50mL高压釜中，6mg（1.0.x.10-2mmol）[铑（I）（（1S，1S'，2R，2R'） - 1,1'-叔丁基 - [2,2'] - 二磷杂环戊烷）（降冰片二烯）]在实施例8中合成并用作催化剂的六氟磷酸盐和1mmol表1中所示的脱氢氨基酸衍生物（或烯酰胺衍生物）。然后，将系统抽空并用氢气吹扫四次。将高压釜恢复至常压，打开旋塞，用注射器从旋塞中快速加入4mL脱气的脱水甲醇，然后关闭。用干冰/乙醇冷却反应器，然后将反应系统再次抽真空并用氢气吹扫四次。在氢气压力设定为预定值后，除去制冷剂，用磁力搅拌器搅拌反应体系直至停止氢气消耗。反应完成后，将反应溶液通过硅胶柱色谱（展开溶剂：乙酸乙酯）以除去催化剂，然后用蒸发器浓缩残余物，得到还原产物。在任何反应中，产率约为100％。用手性HPLC或手性GC分析每种产物的光学纯度（ee）。结果如表1所示。这些结果是以底物：催化剂= 100：1的比例得到的。[表1]

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[68] Organic and Biomolecular Chemistry, 2009, vol. 7, # 9, p. 1890 - 1895
[69] Patent: WO2004/111065, 2004, A1. Location in patent: Page/Page column 37
[70] Patent: WO2004/111065, 2004, A1. Location in patent: Page/Page column 37-38
[71] Patent: WO2004/111065, 2004, A1. Location in patent: Page/Page column 37-38
[72] Patent: WO2004/111065, 2004, A1. Location in patent: Page/Page column 37-38
[73] Patent: WO2004/111065, 2004, A1. Location in patent: Page/Page column 37-38
[74] Patent: WO2004/111065, 2004, A1. Location in patent: Page/Page column 37-38
[75] Patent: US2005/80047, 2005, A1. Location in patent: Page/Page column 13
[76] European Journal of Organic Chemistry, 2009, # 23, p. 3923 - 3929
[77] Advanced Synthesis and Catalysis, 2009, vol. 351, # 5, p. 725 - 732
[78] European Journal of Organic Chemistry, 2009, # 35, p. 6225 - 6230
[79] Organic Letters, 2010, vol. 12, # 1, p. 176 - 179
[80] Chemistry - A European Journal, 2009, vol. 15, # 38, p. 9855 - 9867
[81] Angewandte Chemie - International Edition, 2010, vol. 49, # 21, p. 3627 - 3630
[82] Chemistry - A European Journal, 2010, vol. 16, # 22, p. 6509 - 6517
[83] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 1984 - 1990
[84] Chemistry - A European Journal, 2010, vol. 16, # 22, p. 6495 - 6508
[85] Chemistry - A European Journal, 2010, vol. 16, # 25, p. 7517 - 7526
[86] Angewandte Chemie - International Edition, 2010, vol. 49, # 37, p. 6633 - 6637
[87] Patent: EP1650216, 2006, A1. Location in patent: Page/Page column 18
[88] Chirality, 2010, vol. 22, # 9, p. 844 - 848
[89] Organic Letters, 2010, vol. 12, # 19, p. 4400 - 4403
[90] Organic Letters, 2011, vol. 13, # 3, p. 362 - 365
[91] Dalton Transactions, 2011, vol. 40, # 1, p. 41 - 43
[92] Organometallics, 2011, vol. 30, # 7, p. 1942 - 1950
[93] Journal of the American Chemical Society, 2011, vol. 133, # 43, p. 17176 - 17179
[94] Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14047 - 14062
[95] Chemistry - A European Journal, 2012, vol. 18, # 2, p. 632 - 640
[96] Journal of the American Chemical Society, 2012, vol. 134, # 3, p. 1754 - 1769
[97] Organometallics, 2011, vol. 30, # 24, p. 6718 - 6725
[98] Tetrahedron Asymmetry, 2011, vol. 22, # 24, p. 2104 - 2109
[99] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[100] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4184 - 4188
[101] Chemistry - A European Journal, 2012, vol. 18, # 33, p. 10368 - 10381
[102] Journal of Molecular Catalysis A: Chemical, 2012, vol. 363-364, p. 214 - 222,9

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2. 合成：19914-36-4

35356-70-8

3619-02-1

19914-36-4
参考文献：
[1] Patent: EP918781, 2004, B1. Location in patent: Page 10
[2] Patent: EP1595886, 2005, A1. Location in patent: Page/Page column 18
[3] Patent: EP1595886, 2005, A1. Location in patent: Page/Page column 18
[4] Patent: EP1595886, 2005, A1. Location in patent: Page/Page column 18
[5] Patent: EP1595886, 2005, A1. Location in patent: Page/Page column 18
[6] European Journal of Inorganic Chemistry, 2000, # 9, p. 2011 - 2016
[7] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982, p. 489 - 498
[8] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 4, p. 717 - 724
[9] Journal of Organic Chemistry, 1981, vol. 46, p. 5086 - 5093
[10] Tetrahedron, 1996, vol. 52, # 48, p. 15079 - 15102
[11] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 4, p. 717 - 724
[12] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 7, p. 1920 - 1928
[13] Angewandte Chemie, 1994, vol. 106, # 21, p. 2272 - 2275
[14] Journal of Organic Chemistry, 1995, vol. 60, # 19, p. 6226 - 6228
[15] Journal of Organic Chemistry, 1998, vol. 63, # 13, p. 4168 - 4169
[16] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 8, p. 1967 - 1972
[17] Chemistry Letters, 1989, p. 305 - 308
[18] Journal of Organic Chemistry, 1981, vol. 46, p. 5086 - 5093
[19] Tetrahedron Asymmetry, 1993, vol. 4, # 12, p. 2461 - 2468
[20] Tetrahedron Letters, 1995, vol. 36, # 45, p. 8271 - 8274
[21] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 2988 - 2989
[22] Tetrahedron Letters, 1999, vol. 40, # 39, p. 7059 - 7062
[23] Journal of Organic Chemistry, 1999, vol. 64, # 15, p. 5593 - 5598
[24] Synlett, 1999, # 12, p. 1975 - 1977
[25] Tetrahedron, 1999, vol. 55, # 39, p. 11609 - 11618
[26] Tetrahedron Asymmetry, 1999, vol. 10, # 17, p. 3341 - 3352
[27] Angewandte Chemie - International Edition, 2000, vol. 39, # 8, p. 1428 - 1430
[28] Tetrahedron Letters, 2000, vol. 41, # 33, p. 6333 - 6336
[29] Angewandte Chemie (International Edition in English), 2000, vol. 39, # 21, p. X3889-3890
[30] Journal of Organometallic Chemistry, 2001, vol. 621, # 1-2, p. 158 - 165
[31] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 11, p. 2571 - 2578
[32] Synthesis, 2001, # 4, p. 638 - 646
[33] Tetrahedron Letters, 2001, vol. 42, # 15, p. 2897 - 2899
[34] Tetrahedron Letters, 2001, vol. 42, # 15, p. 2897 - 2899
[35] Tetrahedron Asymmetry, 2001, vol. 12, # 16, p. 2337 - 2342
[36] Chemical Communications, 2002, # 10, p. 1124 - 1125
[37] Tetrahedron Asymmetry, 2002, vol. 13, # 5, p. 465 - 468
[38] European Journal of Organic Chemistry, 2002, # 15, p. 2535 - 2546
[39] European Journal of Inorganic Chemistry, 2003, # 3, p. 556 - 561
[40] Angewandte Chemie - International Edition, 2003, vol. 42, # 7, p. 790 - 793
[41] Tetrahedron Asymmetry, 2002, vol. 13, # 23, p. 2519 - 2522
[42] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4593 - 4596
[43] Journal of Organometallic Chemistry, 2003, vol. 675, # 1-2, p. 91 - 96
[44] Journal of the American Chemical Society, 2003, vol. 125, # 34, p. 10219 - 10227
[45] Russian Journal of Organic Chemistry, 2003, vol. 39, # 3, p. 392 - 396
[46] Organic Letters, 2004, vol. 6, # 9, p. 1433 - 1436
[47] Tetrahedron Asymmetry, 2004, vol. 15, # 14, p. 2155 - 2157
[48] Tetrahedron Asymmetry, 2004, vol. 15, # 14, p. 2273 - 2278
[49] Tetrahedron Asymmetry, 2004, vol. 15, # 13, p. 2011 - 2019
[50] Journal of the American Chemical Society, 2004, vol. 126, # 34, p. 10524 - 10525
[51] Tetrahedron Asymmetry, 2004, vol. 15, # 14, p. 2247 - 2251
[52] Tetrahedron Asymmetry, 2004, vol. 15, # 14, p. 2279 - 2288
[53] Synthesis, 2004, # 12, p. 2047 - 2051
[54] The Journal of organic chemistry, 2004, vol. 69, # 22, p. 7502 - 7510
[55] Tetrahedron Letters, 2005, vol. 46, # 22, p. 3843 - 3846
[56] Tetrahedron Asymmetry, 2004, vol. 15, # 17, p. 2621 - 2631
[57] Journal of Organometallic Chemistry, 2005, vol. 690, # 15, p. 3558 - 3566
[58] Dalton Transactions, 2005, # 15, p. 2557 - 2562
[59] Tetrahedron Asymmetry, 2005, vol. 16, # 14, p. 2455 - 2458
[60] Tetrahedron Asymmetry, 2005, vol. 16, # 22, p. 3676 - 3681
[61] Tetrahedron, 2006, vol. 62, # 5, p. 868 - 871
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[63] Tetrahedron Asymmetry, 2006, vol. 17, # 3, p. 468 - 473
[64] Chemical Communications, 2006, # 21, p. 2292 - 2294
[65] Chemistry - A European Journal, 2004, vol. 10, # 22, p. 5829 - 5835
[66] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2082 - 2087
[67] Angewandte Chemie - International Edition, 2006, vol. 45, # 9, p. 1412 - 1415
[68] Chemical Communications, 2006, # 41, p. 4318 - 4320
[69] Chemistry - A European Journal, 2005, vol. 11, # 22, p. 6701 - 6717
[70] Organic and Biomolecular Chemistry, 2005, vol. 3, # 8, p. 1547 - 1550
[71] Tetrahedron Letters, 2006, vol. 47, # 51, p. 9013 - 9015
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[77] Chemical Communications, 2001, # 24, p. 2702 - 2703
[78] Chemical Communications, 2000, # 11, p. 961 - 962
[79] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5940 - 5942
[80] Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10207 - 10213
[81] Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10207 - 10213
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[86] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7626 - 7631
[87] Tetrahedron Letters, 2004, vol. 45, # 39, p. 7379 - 7381
[88] Chemistry - A European Journal, 2001, vol. 7, # 3, p. 671 - 675
[89] Advanced Synthesis and Catalysis, 2004, vol. 346, # 7, p. 777 - 788
[90] Synthesis, 2006, # 13, p. 2121 - 2128
[91] Tetrahedron, 2007, vol. 63, # 28, p. 6404 - 6414
[92] Chemistry - A European Journal, 2007, vol. 13, # 10, p. 2798 - 2804
[93] European Journal of Organic Chemistry, 2007, # 13, p. 2058 - 2063
[94] Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 609 - 616
[95] Organic Letters, 1999, vol. 1, # 8, p. 1229 - 1232
[96] Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907
[97] Dalton Transactions, 2007, # 34, p. 3750 - 3753
[98] European Journal of Inorganic Chemistry, 2007, # 29, p. 4587 - 4591
[99] Chemical Communications, 2007, # 39, p. 4012 - 4014
[100] Tetrahedron Letters, 2008, vol. 49, # 5, p. 755 - 759

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3. 合成：19914-36-4

35356-70-8

3619-02-1

19914-36-4

N/A

N/A
参考文献：
[1] Journal of the American Chemical Society, 2002, vol. 124, # 23, p. 6649 - 6667
4. 合成：19914-36-4

N/A

3619-02-1

19914-36-4
参考文献：
[1] Patent: WO2008/34809, 2008, A1. Location in patent: Page/Page column 41; 43
[2] Patent: WO2008/34809, 2008, A1. Location in patent: Page/Page column 41; 43
5. 合成：19914-36-4

1417912-28-7

3619-02-1

19914-36-4
产率 合成条件 实验参考步骤
40 % ee With (cycloocta-1,5-diene)-[(S,S)-2,2'-bis(ferrocenyl-phenylphosphino)-1,1'-biphenyl] rhodium tetrafluoroborate; hydrogen In dichloromethane at 20℃; for 16 h; Autoclave K.3。不对称催化氢化典型方法将[Rh（COD）L *] BF4（0.005mmol，1mol％）和底物（0.5mmol）在干燥溶剂（7.5mL）中的溶液引入不锈钢高压釜中。关闭高压釜，用氢气吹扫，然后用氢气加压。在室温下搅拌16小时后，将压力释放至大气压，将溶液转移至圆底烧瓶中。在旋转蒸发器上除去溶剂，得到残余物，将其通过硅胶柱色谱纯化，得到氢化产物。通过HPLC在手性柱上测定对映体过量。配体（1-48）或（1-49）的铑配合物的不对称催化氢化的结果示于表9和10中。表9.铑配合物的不对称催化氢化配体（1-48）底物二膦48 Cond。 （RT 16h）ProductR R2 R R8 Solvant P Conv ee（¾）（百分比）（百分比）63 48a Ph oAn Ph Ph MeOH 4 64 93 61（R）10 100 63（R）20 100 60（R）THF 10 6 ndCH2C12 7表10.配体（I'-49c）的铑配合物的不对称催化氢化
参考文献：
[1] Patent: WO2013/7724, 2013, A1. Location in patent: Page/Page column 88; 89; 90
6. 合成：19914-36-4

67-56-1

5429-56-1

3619-02-1

19914-36-4
参考文献：
[1] Tetrahedron Letters, 2000, vol. 41, # 18, p. 3323 - 3326
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 23, p. 2519 - 2522
7. 合成：19914-36-4

177750-09-3

3619-02-1

19914-36-4
参考文献：
[1] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 20, p. 2762 - 2773
8. 合成：19914-36-4

52386-78-4

19914-36-4
参考文献：
[1] Organometallics, 2011, vol. 30, # 24, p. 6718 - 6725
9. 合成：19914-36-4

57294-56-1

19914-36-4
参考文献：
[1] Journal of Organic Chemistry, 2018,
10. 合成：19914-36-4

26629-33-4

97-69-8

19914-36-4
参考文献：
[1] Tetrahedron, 1987, vol. 43, # 4, p. 771 - 778
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 24, p. 2854 - 2860
[3] Chirality, 2018, vol. 30, # 7, p. 907 - 912
11. 合成：19914-36-4

35356-70-8

21622-00-4

3619-02-1

4167-77-5

19914-36-4
参考文献：
[1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 10, p. 2223 - 2228
12. 合成：19914-36-4

67-56-1

19436-52-3

19914-36-4
参考文献：
[1] Organic Letters, 2007, vol. 9, # 26, p. 5557 - 5560
13. 合成：19914-36-4

14316-06-4

75-36-5

19914-36-4
参考文献：
[1] J. Gen. Chem. USSR (Engl. Transl.), 1968, vol. 3, p. 424 - 433
[2] Zhurnal Obshchei Khimii, 1968, vol. 38, # 3, p. 428 - 439
14. 合成：19914-36-4

124-41-4

N/A

19914-36-4
参考文献：
[1] Carbohydrate Research, 1972, vol. 22, p. 245 - 256
15. 合成：19914-36-4

186581-53-3

5429-56-1

3619-02-1

19914-36-4
参考文献：
[1] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 6012 - 6025
[2] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2960 - 2965
[3] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 6012 - 6025
16. 合成：19914-36-4

7625-53-8

830-03-5

100-02-7

19914-36-4
参考文献：
[1] Canadian Journal of Chemistry, 1991, vol. 69, # 7, p. 1124 - 1130
17. 合成：19914-36-4

186581-53-3

19436-52-3

19914-36-4
参考文献：
[1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 1984 - 1990
18. 合成：19914-36-4

19436-52-3

18107-18-1

19914-36-4
参考文献：
[1] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 775 - 784

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P361立即脱掉所有沾染的衣服。
P362脱掉沾染的衣服。
P363沾染的衣服清洗后方可重新使用。
P370火灾时：
P370 + P376火灾时：如能保证安全，设法堵塞泄漏。
P370 + P378火灾时：使用……灭火。
P370 + P380如果发生火灾：疏散区域。
P370 + P380 + P375火灾时：撤离现场。因有爆炸危险，须远距离灭火。
P371在发生大火和大量泄漏的情况下：
P371 + P380 + P375如发生大火和大量泄漏：撤离现场。因有爆炸危险，须远距离灭火。
P372爆炸危险
P373火烧到爆炸物时切勿救火。
P374在合理的距离内采取正常预防措施进行灭火。
P375因有爆炸危险，须远距离救火。
P376如能保证安全，可设法堵塞泄漏。
P377漏气着火：切勿灭火，除非能够安全地堵塞泄 漏。
P378使用……灭火。
P380撤离现场。
P381在安全的前提下，消除一切火源
P390吸收溢出物，防止材料损坏。
P391收集溢出物。
存储
编码说明
P401存放须遵照……
P402存放于干燥处。
P402 + P404存放在干燥的地方。存放在密闭容器中。
P403存放于通风良好处。
P403 + P233存放在通风良好的地方。 保持容器密闭。
P403 + P235存放在通风良好的地方。 保持凉爽。
P404存放于密闭的容器中。
P405存放处须加锁。
P406存放于耐腐蚀的容器中。
P407堆垛或托盘之间应留有空隙。
P410防日晒。
P410 + P403避免阳光照射。 存放在通风良好的地方。
P410 + P412防日晒。不可暴露在超过50℃/122℉的温度下。
P411贮存温度不超过……
P411 + P235贮存温度不高于……的环境下。保持凉爽。
P412不要暴露在超过50℃/122℉的温度下。
P413温度不超过……时，贮存散货质量大于……
P420单独存放。
P422将内容存储在……
处理
编码说明
P501根据……来处置内装物/容器
P502有关回收和循环使用情况，请咨询制造商或供 应商

危险声明

物理危险
编码说明
H200不稳定爆炸物
H201爆炸物；整体爆炸危险
H202爆炸物；严重迸射危险
H203爆炸物；起火、爆炸或迸射危险
H204起火或迸射危险
H205遇火可能整体爆炸
H220极其易燃气体
H221易燃气体
H222极其易燃气雾剂
H223易燃气雾剂
H224极其易燃液体和蒸气
H225高度易燃液体和蒸气
H226易燃液体和蒸气
H227可燃液体
H228易燃固体
H240加热可能爆炸
H241加热可能起火或爆炸
H242加热可能起火
H250暴露在空气中会自燃
H251自热；可能燃烧
H252数量大时自热；可能燃烧
H260遇水会释放出可燃气体，可能会自燃
H261遇水放出易燃气体
H270可能导致或加剧燃烧；氧化剂
H271可能引起燃烧或爆炸；强氧化剂
H272可能加剧燃烧；氧化剂
H280内装高压气体；遇热可能爆炸
H281内装冷冻气体；可能造成低温灼伤或损伤
H290可能腐蚀金属
健康危险
编码说明
H300吞咽致命
H301吞咽中毒
H302吞咽有害
H303吞咽可能有害
H304吞咽并进入呼吸道可能致命
H305吞咽并进入呼吸道可能有害
H310和皮肤接触致命
H311和皮肤接触有毒
H312和皮肤接触有害
H313皮肤接触可能有害
H314造成严重皮肤灼伤和眼损伤
H315造成皮肤刺激
H316造成轻微皮肤刺激
H317可能导致皮肤过敏反应
H318造成严重眼损伤
H319造成严重眼刺激
H320造成眼刺激
H330吸入致命
H331吸入有毒
H332吸入有害
H333吸入可能有害
H334吸入可能导致过敏或哮喘病症状或呼吸困难
H335可引起呼吸道刺激
H336可引起昏睡或眩晕
H340可能导致遗传性缺陷
H341怀疑会导致遗传性缺陷
H350可能致癌
H351怀疑会致癌
H360可能对生育能力或胎儿造成伤害
H361怀疑对生育能力或胎儿造成伤害
H362可能对母乳喂养 的儿童造成伤害
H370对器官造成损害
H371可能对器官造成损害
H372长期或重复接触会对器官造成伤害
H373长期或重复接触可能对器官造成伤害
环境危险
编码说明
H400对水生生物毒性极大
H401对水生生物有毒
H402对水生生物有害
H410对水生生物毒性极大并具有长期持续影响
H411对水生生物有毒并具有长期持续影响
H412对水生生物有害并具有长期持续影响
H413可能对水生生物造成长期持续有害影响
H420破坏高层大气中的臭氧，危害公共健康和环境

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