CAS号：3029-19-4

CAS号3029-19-4, 是有机发光二极管类化合物, 分子量为230.26, 分子式C17H10O, 标准纯度98%, 毕得医药(Bidepharm)提供3029-19-4批次质检（如NMR, HPLC, GC）等检测报告。

芘-1-甲醛 (请以英文为准,中文仅做参考)

1-Pyrenecarboxaldehyde , 3-Pyrenylaldehyde

货号：BD41575 1-Pyrenecarboxaldehyde 标准纯度：, 98%

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 :	1-Pyrenecarboxaldehyde , 3-Pyrenylaldehyde
中文名称 :	芘-1-甲醛(请以英文为准,中文仅做参考)
CAS号 :	3029-19-4
分子式 :	C₁₇H₁₀O
线性分子式 :	-
分子量 :	230.26
MDL NO :	MFCD00004139
沸点 :	-
Pubchem ID :	232848
InChIKey :	RCYFOPUXRMOLQM-UHFFFAOYSA-N

常用 :

SDS-BD41575

2D :

3D :

【用途一】

计算化学

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	16
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	75.53
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.	2.3
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	4.45
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.4
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.	3.75
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	4.94
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.97

Water Solubility

Log S (ESOL)? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.66
Solubility	0.005 mg/ml ; 0.0000217 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.53
Solubility	0.00684 mg/ml ; 0.0000297 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-6.54
Solubility	0.0000666 mg/ml ; 0.000000289 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	Yes
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	Yes
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.	-4.55 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	2.0 alert
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	2.0
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)	1.0

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。

1~41 ►

1. 合成：3029-19-4

24463-15-8

3029-19-4

产率

合成条件

实验步骤

93%

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In acetonitrile at 25℃; for 1 h;

一般步骤：向圆底烧瓶中加入醇（2mmol），CuOTf（0.1mmol，0.05当量）（S）-5-（吡咯烷-2-基）-1H-四唑（0.1mmol，0.05当量）， TEMPO（0.1mmol，0.05当量），DMAP（0.15mmol，0.075当量）和CH 3 CN（5ml）。将反应混合物在25℃下搅拌至空气直至反应完成，如通过TLC监测的。完成后，在真空下蒸发CH 3 CN。然后将残余物用CH 2 Cl 2（5ml）稀释，通过硅胶塞过滤，得到所需产物。

86%

With C₃₅H₂₈Cl₂N₅PRu; potassium tert-butylate In toluene at 50℃; for 6 h;

一般程序：按照一般程序，在碱存在下使用络合物1作为催化剂。在圆底烧瓶中，将1mmol底物，0.005mmol催化剂（3.6mg）和0.010mmol tBuOK（1.1mg）在10mL甲苯中混合。将反应混合物在有氧条件下在50℃下加热，连续搅拌6小时，然后在减压下用旋转蒸发器蒸发溶剂。由此获得的粗产物在制备性硅胶GF-254 TLC板上纯化，使用乙酸乙酯：己烷（1:10）溶剂混合物作为洗脱剂。通过NMR光谱表征氧化产物（参见图S4-S32）。

80%

With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2 h; Green chemistry

一般程序：将醇（2mmol）加入到IBS（0.02mmol，0.01当量），过硫酸氢钾（2.2mmol，1.1当量）和3wt％CTAB溶液（5mL）的溶液中。将混合物在室温下搅拌。通过TLC监测反应。完成后，将溶液用CH 2 Cl 2（3×10mL）萃取。然后将合并的有机相通过硅胶垫过滤并真空蒸发，得到所需产物。

参考文献：

[1] Chemical Communications, 2003, # 6, p. 758 - 759
[2] Inorganic Chemistry, 2016, vol. 55, # 12, p. 6114 - 6123
[3] Inorganic Chemistry, 2017, vol. 56, # 22, p. 14084 - 14100
[4] Tetrahedron, 2014, vol. 70, # 52, p. 9791 - 9796
[5] Chemistry - A European Journal, 2016, vol. 22, # 26, p. 8814 - 8822
[6] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7165 - 7175
[7] Inorganica Chimica Acta, 2019, vol. 484, p. 160 - 166
[8] Journal of Materials Chemistry, 2007, vol. 17, # 29, p. 3030 - 3036
[9] Journal of Chemical Research, 2014, vol. 38, # 7, p. 427 - 431
[10] Inorganic Chemistry, 2018, vol. 57, # 19, p. 11995 - 12009
[11] ACS Catalysis, 2018, vol. 8, # 6, p. 5425 - 5430
[12] Tetrahedron Letters, 2002, vol. 43, # 40, p. 7179 - 7183
[13] Journal of the American Chemical Society, 2014, vol. 136, # 21, p. 7543 - 7546
[14] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6077 - 6081
[15] Angew. Chem., 2018, vol. 130, p. 6185 - 6189,5
[16] Inorganic Chemistry, 2018, vol. 57, # 12, p. 6816 - 6824

2. 合成：3029-19-4

129-00-0

4885-02-3

3029-19-4

产率

合成条件

实验步骤

96%

With titanium tetrachloride In dichloromethane at 0 - 20℃; for 2.50 h;

在0℃下，向搅拌的CH 2 Cl 2（90mL）芘（2.022g，10mmol）溶液中加入Cl 2 CHOCH 3（1.2mL，13mmol）。向该溶液中缓慢加入TiCl 4（2.0mL，18mmol）。溶液的颜色从黄色变为紫红色。将混合物在0℃下搅拌1小时并在室温下搅拌1.5小时。将溶液倒入冷水（100mL）中，搅拌直至颜色从紫红色变为黄色。将混合物用CH 2 Cl 2（50mL×2）萃取。将合并的有机层用盐水（50mL）洗涤，分离，经MgSO 4干燥，过滤，并真空浓缩，得到1-甲酰基芘（2.24g，96％收率）。黄色固体; 1H NMR（400Mz，CDCl3）d 8.08-8.13（m，2H），8.23-8.36（m，5H），8.47（d，J = 8.0Hz，1H），9.45（d，J = 9.6Hz，1H），10.80（s，1H）ppm。向搅拌的CH 2 Cl 2（20mL）1-甲酰基芘（0.46g，2mmol）溶液中加入m-CPBA（0.68g，3mmol），将所得溶液在回流下搅拌24小时，然后真空浓缩。向残余物中加入THF（5mL），MeOH（5mL）和25％KOH水溶液（0.6mL），得到混合物，将其在室温下搅拌4小时，然后真空浓缩。将残余物溶于2％KOH水溶液（10mL）中。将溶液用CH 2 Cl 2（10mL×2）萃取。将合并的有机层用冰冷却的HCl水溶液（pH = 2）洗涤，分离，经MgSO 4干燥，过滤，并真空浓缩，得到残余物，进行硅胶柱色谱（洗脱液; CHCl 3，Rf = 0.3）。）得到1-羟基芘（3,0.223g，50％收率）。灰色固体; 1H NMR（400Mz，CDCl3）d 5.70（brs，1H），7.48（d，J = 6.4Hz，1H），7.91（d，J = 8.8Hz，1H），7.96-7.99（m，2H），8.03 -8.07（m，2H），8.10-8.13（m，2H），8.35（d，J = 7.6Hz，1H）。

参考文献：

[1] Tetrahedron Letters, 2017, vol. 58, # 46, p. 4377 - 4380
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 24, p. 3127 - 3138
[3] Organic Preparations and Procedures International, 1997, vol. 29, # 3, p. 321 - 330
[4] Journal of the American Chemical Society, 2008, vol. 130, p. 12846 - 12847
[5] ACS Catalysis, 2016, vol. 6, # 11, p. 7398 - 7408

3. 合成：3029-19-4

129-00-0

39828-35-8

3029-19-4

273736-52-0

产率

合成条件

实验步骤

86%

With hydrogenchloride In dichloromethane

1-（2,4-二甲氧基苯甲酰基）芘（2a）将芘（10.1g; 0.05mol）和2,4-二甲氧基苯甲酰氯（10g; 0.05mol）溶于400ml无水二氯甲烷中。在剧烈搅拌下，在0℃下在1小时内将少量无水氯化铝（6.6g; 0.05mol）加入到反应混合物中。将反应混合物在0℃下搅拌另外2小时，在室温下搅拌2小时，然后倒入冰和HCl（500ml）的混合物中，并转移到分液漏斗中。用水（1×500ml），饱和NaHCO 3（2×500ml）和饱和NaCl（1×500ml）洗涤有机层。蒸发有机部分，用甲苯重结晶，得到芘基酮，为白色固体（15.7g; 86％）。实测值：C，82.09; H，4.81。 C25H18O3（MW366.41）要求C，81.95; H，4.95％。 1H-NMR（CDCl3，d）：8.65-6.45（m，12H，arom。），3.91（s，3H，OCH3），3.55（s，3H，OCH3）。质谱，MALDI-TOF：388.89（MI + Na; 15），366.89（100），203.82（40）。计算出的C25H18O3的精确质量：366.12559;发现366.12617 [1.6 ppm的错误]。

参考文献：

[1] Patent: US2003/175742, 2003, A1

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浓度
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浓度 x 体积 x 分子量 = 质量

合成路线

1. 合成：3029-19-4

24463-15-8

3029-19-4

产率

合成条件

实验参考步骤

93%

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In acetonitrile at 25℃; for 1 h;

86%

With C₃₅H₂₈Cl₂N₅PRu; potassium tert-butylate In toluene at 50℃; for 6 h;

80%

With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2 h; Green chemistry

参考文献：

2. 合成：3029-19-4

129-00-0

4885-02-3

3029-19-4

产率

合成条件

实验参考步骤

96%

With titanium tetrachloride In dichloromethane at 0 - 20℃; for 2.50 h;

参考文献：

3. 合成：3029-19-4

129-00-0

39828-35-8

3029-19-4

273736-52-0

产率

合成条件

实验参考步骤

86%

With hydrogenchloride In dichloromethane

参考文献：

[1] Patent: US2003/175742, 2003, A1

4. 合成：3029-19-4

24463-15-8

16640-68-9

3029-19-4

103698-30-2

N/A

参考文献：

[1] Angewandte Chemie - International Edition, 2002, vol. 41, # 24, p. 4740 - 4743

5. 合成：3029-19-4

129-00-0

68-12-2

3029-19-4

参考文献：

[1] Journal of the Indian Chemical Society, 2008, vol. 85, # 9, p. 959 - 961
[2] Dyes and Pigments, 2011, vol. 89, # 3, p. 199 - 211
[3] Frontiers of Chemistry in China, 2010, vol. 5, # 2, p. 193 - 199
[4] New Journal of Chemistry, 2018, vol. 42, # 22, p. 18297 - 18304

6. 合成：3029-19-4

24463-15-8

16640-68-9

N/A

3029-19-4

74833-81-1

N/A

参考文献：

[1] European Journal of Organic Chemistry, 2006, # 19, p. 4367 - 4378

7. 合成：3029-19-4

1714-29-0

68-12-2

3029-19-4

参考文献：

[1] Organic Syntheses, 2016, vol. 93, p. 100 - 114
[2] Russian Chemical Bulletin, 2014, vol. 63, # 6, p. 1312 - 1316
[3] Izv. Akad. Nauk, Ser. Khim., 2014, # 6, p. 1312 - 1316,5

8. 合成：3029-19-4

2381-21-7

3029-19-4

参考文献：

[1] Journal of Organic Chemistry, 1983, vol. 48, # 5, p. 749 - 751

9. 合成：3029-19-4

164461-18-1

298-12-4

3029-19-4

参考文献：

[1] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8201 - 8205
[2] Angew. Chem., 2017, vol. 129, # 28, p. 8313 - 8317,5

10. 合成：3029-19-4

129-00-0

93-61-8

3029-19-4

参考文献：

[1] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 12941 - 12944
[2] Chemistry - A European Journal, 2010, vol. 16, # 30, p. 9154 - 9163
[3] Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,35, 107

11. 合成：3029-19-4

93265-41-9

3029-19-4

N/A

参考文献：

[1] Journal of the American Chemical Society, 1986, vol. 108, # 15, p. 4498 - 4504
[2] Journal of the American Chemical Society, 1986, vol. 108, # 15, p. 4498 - 4504
[3] Journal of the American Chemical Society, 1986, vol. 108, # 15, p. 4498 - 4504

12. 合成：3029-19-4

2595-90-6

3029-19-4

参考文献：

[1] Chemistry Letters, 2005, vol. 34, # 2, p. 194 - 195

13. 合成：3029-19-4

N/A

3029-19-4

参考文献：

[1] Journal of the American Chemical Society, 1987, vol. 109, # 1, p. 278 - 279

14. 合成：3029-19-4

N/A

1714-29-0

68-12-2

3029-19-4

1448061-63-9

参考文献：

[1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 767 - 774

15. 合成：3029-19-4

N/A

1714-29-0

68-12-2

3029-19-4

1448061-62-8

参考文献：

[1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 767 - 774

16. 合成：3029-19-4

1386958-83-3

56790-59-1

3029-19-4

参考文献：

[1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846

17. 合成：3029-19-4

N/A

3029-19-4

参考文献：

[1] Journal of the American Chemical Society, 1987, vol. 109, # 1, p. 278 - 279

18. 合成：3029-19-4

1224300-86-0

3029-19-4

参考文献：

[1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 7011 - 7015

19. 合成：3029-19-4

129-00-0

141-82-2

3029-19-4

19694-02-1

123295-70-5

参考文献：

[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 545 - 550

20. 合成：3029-19-4

129-00-0

3029-19-4

参考文献：

[1] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1119,1124
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 1031

21. 合成：3029-19-4

1067915-14-3

3029-19-4

参考文献：

[1] Journal of the American Chemical Society, 2008, vol. 130, p. 12846 - 12847

22. 合成：3029-19-4

1067915-21-2

3029-19-4

参考文献：

[1] Journal of the American Chemical Society, 2008, vol. 130, p. 12846 - 12847

23. 合成：3029-19-4

220196-58-7

3029-19-4

24463-15-8

91385-15-8

参考文献：

[1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750

24. 合成：3029-19-4

51694-22-5

2595-90-6

56790-59-1

3029-19-4

参考文献：

[1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846

25. 合成：3029-19-4

873397-62-7

3029-19-4

参考文献：

[1] Australian Journal of Chemistry, 1956, vol. 9, p. 222,226

26. 合成：3029-19-4

129-00-0

141-82-2

64-19-7

3029-19-4

19694-02-1

123295-70-5

参考文献：

[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 545 - 550

27. 合成：3029-19-4

220196-58-7

142-08-5

822-89-9

3029-19-4

91385-15-8

参考文献：

[1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750

28. 合成：3029-19-4

3264-21-9

3029-19-4

参考文献：

[1] Australian Journal of Chemistry, 1956, vol. 9, p. 222,226

29. 合成：3029-19-4