8,9-二氢-5H-苯并[7]轮烯-7(6H)-酮

CAS号：37949-03-4

CAS号37949-03-4, 是酮类化合物, 分子量为160.21, 分子式C11H12O, 标准纯度95%, 毕得医药(Bidepharm)提供37949-03-4批次质检（如NMR, HPLC, GC）等检测报告。

8,9-二氢-5H-苯并[7]轮烯-7(6H)-酮 (请以英文为准,中文仅做参考)

8,9-Dihydro-5H-benzo[7]annulen-7(6H)-one , 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-7-one

货号：BD222148 8,9-Dihydro-5H-benzo[7]annulen-7(6H)-one 标准纯度：, 95%

标准纯度	包装	价格	上海	深圳	天津	武汉	成都	VIP价格	数量

检测信息
批次：
纯度：批次查询可见
COA MS HPLC LC-MS Microanalysis

产品名称 :	8,9-Dihydro-5H-benzo[7]annulen-7(6H)-one , 6,7,8,9-Tetrahydro-5H-benzo[7]annulen-7-one
中文名称 :	8,9-二氢-5H-苯并[7]轮烯-7(6H)-酮(请以英文为准,中文仅做参考)
CAS号 :	37949-03-4
分子式 :	C₁₁H₁₂O
线性分子式 :	-
分子量 :	160.21
MDL NO :	MFCD09867716
沸点 :	-
Pubchem ID :	12234485
InChIKey :	MRLBDJHIJZHYMK-UHFFFAOYSA-N

常用 :

SDS-BD222148

2D :

3D :

【用途一】

计算化学

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	48.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.91
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.13
Log P_o/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.	2.3
Log P_o/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	3.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.31

Water Solubility

Log S (ESOL)? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.4
Solubility	0.637 mg/ml ; 0.00398 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.88
Solubility	2.11 mg/ml ; 0.0131 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	-3.66
Solubility	0.0349 mg/ml ; 0.000218 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	Yes
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.	-5.93 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	2.0
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)	1.64

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。

1~25 ►

1. 合成：37949-03-4

24790-66-7

37949-03-4

产率

合成条件

实验步骤

84%

Stage #1: With sulfuric acid In water; acetonitrileInert atmosphere
Stage #2: With sodium hydroxide In diethyl ether; water; acetonitrile

制备3 5,6,8,9-四氢 - 苯并环庚烯-7-酮（具有式II的化合物）7-氧代-5,6,8,9-四氢苯并环庚烯-6,8-二羧酸二甲酯的异构体混合物（80 g）根据制备2获得的物质在氩气下在3M硫酸水溶液（300mL）和乙腈（50mL）溶液中回流过夜。将混合物用乙醚稀释，用2M氢氧化钠水溶液（3×300mL）中和，用硫酸镁干燥并蒸发至干。在97-98℃，0.4-0.5托下蒸馏出残余物，得到无色晶体（26.1g，84％，α，α'-二溴 - 邻二甲苯）。熔点：43-44℃.1H-NMR（CDCl3）：7.23（m，4Hal）; 2.91（m，2H-C（6），2H-C（8））; 2.62（m，2H-C（5），2H-C（9））。

81%

With hydrogenchloride; water In methanol at 90℃; for 12 h;

将6M HCl加入到溶解在CH 3 OH（3mL）中的二酯10（100.4mg，0.37mmol，1当量）的溶液中，并将混合物在90℃下搅拌12小时。将混合物用EtOAc（3×5mL）萃取，将EtOAc层干燥（Na 2 SO 4），过滤并将溶剂真空蒸发。通过fc（d = 1.5cm，1 = 15cm，v = 10mL，环己烷/ EtOAc 8：2，Rf = 0.27）纯化粗产物，得到无色固体，mp42℃，产量47.4mg（81％））。 C11H12O（160.2g / mol）。 FT-IR（纯）：ν（cm -1）= 2936（C-H），1694（C = O），748（1,2-二取代。）。 1H NMR（CDCl3）：δ（ppm）= 2.59-2.65（m，4H，2×6-H，2×8-H），2.89-2.95（m，4H，2×5-H，2×9- H），7.22（s，4H，Ar-H）。 13C NMR（CDCl3）：δ（ppm）= 30.7（2C，C-5，C-9）44.8（2C，C-6，C-8），127.3（2C，Carom），129.3（2C，Carom）， 140.7（2C，Cqarom），211.4（1C，C = O）。

57%

Stage #1: With potassium hydroxide; water In ethanol at 85℃; for 17 h;
Stage #2: With hydrogenchloride In water at 0℃;

B.将粗制的7-氧代-6,7,8,9-四氢-5H-苯并[7]环壬烷-6,8-二甲酸二甲酯溶于200mL乙醇（EtOH）中，然后溶于100mL 2N KOH中。。将所得混合物在85℃下回流17小时。冷却至环境温度后，蒸发挥发物。在0℃向残余物中加入120mL 2N HCl，粗产物用EtOAc（200mL×2）萃取。将合并的萃取液用盐水洗涤。干燥（MgSO 4），过滤并浓缩后，通过硅胶快速柱色谱法（己烷/ EtOAc 8：1）纯化残余物，得到6.6g（57％）8,9-二氢-5H-苯并[7]。 ] annulen-7（6H） - 酮，为白色固体：mp40-41℃; 1 H NMR（300MHz，CDCl 3）δ：7.21（m，4H），2.94-2.90（m，4H），2.63-2.60（m，4H）; LC-MS：161（M + H）+。

57%

Stage #1: With potassium hydroxide In ethanol at 85℃; for 17 h;
Stage #2: With hydrogenchloride In water at 0℃;

B.将粗制的7-氧代-6,7,8,9-四氢-5H-苯并[7]环壬烷-6,8-二甲酸二甲酯溶于200mL乙醇（EtOH）中，然后100mL 2 N KOH。将所得混合物在85℃下回流17小时。冷却至环境温度后，蒸发挥发物。在0℃向残余物中加入120mL 2N HCl，粗产物用EtOAc（200mL×2）萃取。将合并的萃取液用盐水洗涤。干燥（MgSO 4），过滤并浓缩后，通过硅胶快速柱色谱法（己烷/ EtOAc 8：1）纯化残余物，得到6.6g（57％）7-氧代-6,7,8,9。 -tetrahydro-5 / - / - 苯并[7]环烯烃，为白色固体：mp40-41℃; 1 H NMR（300MHz，CDCl 3）δ：7.21（m，4H），2.94-2.90（m，4H），2.63-2.60（m，4H）; LC-MS：161（M + H）+。

参考文献：

[1] Patent: US2010/69504, 2010, A1. Location in patent: Page/Page column 5
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6638 - 6646
[3] Patent: WO2008/83367, 2008, A2. Location in patent: Page/Page column 132-133
[4] Patent: WO2010/5876, 2010, A2. Location in patent: Page/Page column 55-56
[5] Drugs of the Future, 2018, vol. 43, # 9, p. 645 - 653

2. 合成：37949-03-4

56613-15-1

37949-03-4

产率

合成条件

实验步骤

52%

Stage #1: With sodium hydride In tolueneHeating / reflux
Stage #2: With acetic acid In water; toluene at 20℃;

将氢化钠（60％在矿物油中，1.2g，29.9mmol）和催化量的叔丁醇合并在甲苯（100mL）中。使溶液回流并滴加E54A（10g，29.9mmol）的甲苯（30mL）溶液过夜，同时保持溶液回流。将反应冷却至室温后，滴加冰醋酸（4mL），然后快速加入冰水。分层。用盐水（2.x.）和水（2.x.）洗涤有机层;用硫酸钠干燥;过滤;并且集中。将粗残余物加入到甲醇（70mL）和6N盐酸（30mL）的混合物中并加热回流3小时。冷却至室温后，将溶液用乙酸乙酯稀释，并用饱和碳酸氢钠（2.x.）和盐水（2.x.）洗涤;用硫酸钠干燥;并且集中。残余物在硅胶上进行柱色谱（10％乙酸乙酯/己烷），得到2.5g（52％）E54B。 1H-NMR（CDCl3,300MHz）δ2.8（m，4H），2.94（m，4H），7.36（s，4H）。

参考文献：

[1] Patent: US2007/249583, 2007, A1. Location in patent: Page/Page column 103-104
[2] Patent: WO2004/69832, 2004, A2. Location in patent: Page 101-102

3. 合成：37949-03-4

4443-91-8

37949-03-4

参考文献：

[1] Tetrahedron, 1983, vol. 39, # 7, p. 1041 - 1060

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合成路线

1. 合成：37949-03-4

24790-66-7

37949-03-4

产率

合成条件

实验参考步骤

84%

Stage #1: With sulfuric acid In water; acetonitrileInert atmosphere
Stage #2: With sodium hydroxide In diethyl ether; water; acetonitrile

81%

With hydrogenchloride; water In methanol at 90℃; for 12 h;

57%

Stage #1: With potassium hydroxide; water In ethanol at 85℃; for 17 h;
Stage #2: With hydrogenchloride In water at 0℃;

57%

Stage #1: With potassium hydroxide In ethanol at 85℃; for 17 h;
Stage #2: With hydrogenchloride In water at 0℃;

参考文献：

2. 合成：37949-03-4

56613-15-1

37949-03-4

产率

合成条件

实验参考步骤

52%

Stage #1: With sodium hydride In tolueneHeating / reflux
Stage #2: With acetic acid In water; toluene at 20℃;

参考文献：

[1] Patent: US2007/249583, 2007, A1. Location in patent: Page/Page column 103-104
[2] Patent: WO2004/69832, 2004, A2. Location in patent: Page 101-102

3. 合成：37949-03-4

4443-91-8

37949-03-4

参考文献：

[1] Tetrahedron, 1983, vol. 39, # 7, p. 1041 - 1060

4. 合成：37949-03-4

N/A

37949-03-4

参考文献：

[1] Organic Letters, 2015, vol. 17, # 23, p. 5820 - 5823

5. 合成：37949-03-4

N/A

37949-03-4

参考文献：

[1] Organic Letters, 2015, vol. 17, # 23, p. 5820 - 5823

6. 合成：37949-03-4

N/A

37949-03-4

参考文献：

[1] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 1035 - 1041

7. 合成：37949-03-4

33188-51-1

37949-03-4

参考文献：