87099-71-6 (5-O-香豆酰基奎宁酸,5-O-Coumaroylquinic Acid)

快速询单

结构式：

5-O-香豆酰基奎宁酸MOL文件

CAS号：

87099-71-6

中文名称：

5-O-香豆酰基奎宁酸

英文名称：

5-O-Coumaroylquinic Acid

分子式：

C₁₆H₁₈O₈

分子量：

338.309325695038

植物源：

黑茶藨子西洋梨

5-O-香豆酰基奎宁酸(87099-71-6)名称与标识符

名称

中文别名：

3-O-对羟基肉桂酰奎宁酸;5-O-对香豆酰基奎宁酸;

英文别名：

Cyclohexanecarboxylic acid,1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-,(1R,3R,4S,5R)-;1AF7V9VW0S;o-Coumaroylquinic acid;3-p-coumaroylquinic acid;3-O-Coumaroylquinic acid;3-O-p-Coumaroylquinic acid;3-p-Coqa;p-Coumaroyl 5-O-quinate;5-p-Coumaroylquinic acids;5-O-p-Coumaroylquinic acid;Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-(((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (1R,3R,4S,5R)-;1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9CI;870;(1R,3R,4S,5R)-1,3,4-Trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]cyclohexanecarboxylic acid (ACI);Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)- (9CI);Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [1R-[1α,3β,4α,5α(E)]]- (ZCI);5-O-Coumaroylquinic acid;32451-86-8;(1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid;UNII-1AF7V9VW0S;NCGC00384821-01;87099-71-6;DTXSID301344004;5-Coumaroyl quinic acid;AKOS040740142;(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid;CHEBI:75499;CHEBI:167530;(1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid;SCHEMBL21240786;FS-8565;GLXC-19216;Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (1R,3R,4S,5R)-;

标识符

InChIKey：

BMRSEYFENKXDIS-QHAYPTCMSA-N

Inchi：

1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14+,16-/m1/s1

SMILES：

O([C@H]1[C@@H](O)[C@H](O)C[C@](O)(C(=O)O)C1)C(=O)/C=C/C1C=CC(O)=CC=1

5-O-香豆酰基奎宁酸(87099-71-6)物化性质

计算特性

精确分子量 : 338.10016753g/mol
氢键供体数量 : 5
氢键受体数量 : 8
可旋转化学键数量 : 5
同位素质量 : 338.10016753g/mol
重原子数量 : 24
复杂度 : 496
同位素原子数量 : 0
确定原子立构中心数量 : 4
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 1
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : -0.1
拓扑分子极性表面积 : 145

5-O-香豆酰基奎宁酸(87099-71-6)推荐厂家更多厂家(17)

公司名称	手机号/电话	联系人	QQ	询单
成都麦德生科技有限公司	18140204969 028-81183388	黄刚强	3003805117	询单
江苏永健医药科技有限公司	17701422016	韩经理	3587493084	询单
上海源叶生物科技有限公司	15026964105 15026964105	汤思磊	2881489226	询单
成都乐美天医药科技有限公司	18228097334 028-85003950	华松涛	2885373749	询单
天津普西唐生物医药科技有限公司	15801484223 15801484223	唐召锋	3003463702	询单
四川维克奇生物科技有限公司	13348961525	杨洋	2851167780	询单
湖北萃园生物科技有限公司	18162756256 027-84759766	金生 Jeremy	1197063825	询单
江苏永健医药科技有限公司	17701422016	韩经理	3587493084	询单
西安德而塔生物科技有限公司	18133906270 18133906270	张女士	2590956145	询单
西安德而塔生物科技有限公司	18133906270 18133906270	张女士	2590956145	询单

5-O-香豆酰基奎宁酸(87099-71-6)合成路线

合成路线：1 步

1629056-61-6

_73%

87099-71-6

反应条件：

1.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
1.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：2 步

61844-66-4

1629056-53-6

87099-71-6

反应条件：

1.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
1.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
2.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：3 步

1629056-51-4

87099-71-6

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid , Tetrahydrofuran ; 13 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
2.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
2.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
3.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：3 步

84184-55-4

87099-71-6

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran , Water ; 21 h, rt
1.2 Reagents: Sodium bisulfate Solvents: Water ; neutralized, rt
2.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
2.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
3.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：4 步

19367-38-5

107-30-2

87099-71-6

反应条件：

1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ; 21 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran , Water ; 21 h, rt
2.2 Reagents: Sodium bisulfate Solvents: Water ; neutralized, rt
3.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
3.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
4.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：4 步

1629056-52-5

824-94-2

87099-71-6

反应条件：

1.1 Reagents: Cesium carbonate Solvents: Dimethylformamide ; 2 h, 80 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid , Tetrahydrofuran ; 13 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
3.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
3.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
4.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：4 步

213536-05-1

824-94-2

87099-71-6

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ; 75 min, rt
1.2 Reagents: Sodium bisulfate ; neutralized, rt
1.3 Reagents: Cesium carbonate Solvents: Dimethylformamide ; 2 h, 80 °C
1.4 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid , Tetrahydrofuran ; 13 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
3.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
3.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
4.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：5 步

176798-26-8

18162-48-6

87099-71-6

反应条件：

1.1 Reagents: Imidazole Solvents: Dimethylformamide ; 25 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ; 75 min, rt
2.2 Reagents: Sodium bisulfate ; neutralized, rt
2.3 Reagents: Cesium carbonate Solvents: Dimethylformamide ; 2 h, 80 °C
2.4 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid , Tetrahydrofuran ; 13 h, rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
4.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
4.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
5.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：5 步

213536-05-1

87099-71-6

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ; 75 min, rt
1.2 Reagents: Sodium bisulfate ; neutralized, rt
2.1 Reagents: Cesium carbonate Solvents: Dimethylformamide ; 2 h, 80 °C
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid , Tetrahydrofuran ; 13 h, rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
4.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
4.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
5.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：5 步

501-98-4

67-56-1

87099-71-6

反应条件：

1.1 Reagents: Benzene, diethenyl-, polymer with ethenylbenzene and ethenylethylbenzene, sulfon… Solvents: Methanol ; 90 h, reflux
2.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ; 21 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water ; rt
3.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran , Water ; 21 h, rt
3.2 Reagents: Sodium bisulfate Solvents: Water ; neutralized, rt
4.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
4.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
5.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：6 步

反应条件：

1.1 Reagents: Trimethyl orthoformate , (-)-Camphorsulfonic acid Solvents: Methanol ; 45 h, 85 °C
2.1 Reagents: Imidazole Solvents: Dimethylformamide ; 25 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water ; rt
3.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ; 75 min, rt
3.2 Reagents: Sodium bisulfate ; neutralized, rt
3.3 Reagents: Cesium carbonate Solvents: Dimethylformamide ; 2 h, 80 °C
3.4 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Acetic acid , Tetrahydrofuran ; 13 h, rt
4.2 Reagents: Sodium bicarbonate Solvents: Water ; rt
5.1 Reagents: Tosyl chloride , Diisopropylethylamine Solvents: 1,2-Dichloroethane ; 30 min, rt
5.2 Reagents: 1-Methylimidazole Solvents: 1,2-Dichloroethane ; 2 h, 40 °C
5.3 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Pentamethylbenzene , Boron trichloride Solvents: Dichloromethane ; 10 min, -40 °C; 3 h, -40 °C → 0 °C
6.2 Reagents: Water

参考文献：

Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate

Oyama, Kin-ichi; et al, Tetrahedron, 2015, 71(20), 3120-3130

合成路线：1 步

2088176-61-6

_50%

87099-71-6

1108200-72-1

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

合成路线：1 步

2088176-62-7

_22%

87099-71-6

1108200-72-1

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

合成路线：2 步

反应条件：

1.1 Reagents: Pyridine , (1S,3R,4R,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3-dihydroxy-6-oxabicyc… Catalysts: 4-(Dimethylamino)pyridine ; 24 h, rt
1.2 Reagents: Water ; cooled
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2 - 3
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

合成路线：2 步

反应条件：

1.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 24 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 2 - 3
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

合成路线：3 步

反应条件：

1.1 Catalysts: Trimethyl orthoformate , (-)-Camphorsulfonic acid ; 15 h, reflux
2.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 24 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; pH 2 - 3
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

合成路线：3 步

反应条件：

1.1 Reagents: Imidazole Solvents: Dimethylformamide ; 30 min, 0 °C; 1 h, rt
2.1 Reagents: Pyridine , (1S,3R,4R,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3-dihydroxy-6-oxabicyc… Catalysts: 4-(Dimethylamino)pyridine ; 24 h, rt
2.2 Reagents: Water ; cooled
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2 - 3
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427

合成路线：3 步

27542-85-4

87099-71-6

1108200-72-1

反应条件：

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Toluene ; 2 h, -5 °C; overnight, rt
2.1 Reagents: Pyridine , (1S,3R,4R,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3-dihydroxy-6-oxabicyc… Catalysts: 4-(Dimethylamino)pyridine ; 24 h, rt
2.2 Reagents: Water ; cooled
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2 - 3
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 6 d, rt

参考文献：

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

Gutierrez Ortiz, Anggy Lusanna; et al, Tetrahedron: Asymmetry, 2017, 28(3), 419-427