4-[1-Hydroxy-1-(4-methoxy-phenyl)-ethyl]-5-[hydroxy-(1-methyl-1H-indol-2-yl)-methyl]-4,5-dihydro-thiophene-2-carboxylic acid methyl ester | 682344-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[1-Hydroxy-1-(4-methoxy-phenyl)-ethyl]-5-[hydroxy-(1-methyl-1H-indol-2-yl)-methyl]-4,5-dihydro-thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 3-[1-hydroxy-1-(4-methoxyphenyl)ethyl]-2-[hydroxy-(1-methylindol-2-yl)methyl]-2,3-dihydrothiophene-5-carboxylate
• CAS: 682344-68-9
• 化学式: C₂₅H₂₇NO₅S
• 分子量: 453.559
• InChiKey: XAIXMOMQXAHWGS-UHFFFAOYSA-N

物化性质

• 沸点：
  674.1±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  80.92
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[1-Hydroxy-1-(4-methoxy-phenyl)-ethyl]-5-[hydroxy-(1-methyl-1H-indol-2-yl)-methyl]-4,5-dihydro-thiophene-2-carboxylic acid methyl ester 在 palladium diacetate 、 potassium carbonate 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 、 苯 为溶剂， 反应 26.0h， 生成 Methyl 4-[1-(4-methoxyphenyl)vinyl]-5-[(1-methyl-1H-indol-2-yl)carbonyl]-2-thiophenecarboxylate
  参考文献：
  名称：

  Carbazolothiophene-2-carboxylic acid derivatives as endothelin receptor antagonists

  摘要：

  The SmI2-promoted three-component coupling reaction of thiophene-2-carboxylate, indole-2-carbaldehyde and acetophenone provides an expedient route to a series of tetracyclic carbazolothiophene compounds bearing the indole and thiophene rings. Among these samples, 9-benzyl-4-methyl-4-(4-hydroxyphenyl)-10-oxo-4,10-dihydrocarbazolo[2,3-b]thiophene-2-carboxylic acid (18) shows the most potent inhibition against the endothelin-1 induced increase of intracellular calcium ion concentration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.067
• 作为产物：
  描述：

  1-甲基吲哚-2-甲醛 、 噻吩-2-羧酸甲酯 、 对甲氧基苯乙酮 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 11.5h， 以77%的产率得到4-[1-Hydroxy-1-(4-methoxy-phenyl)-ethyl]-5-[hydroxy-(1-methyl-1H-indol-2-yl)-methyl]-4,5-dihydro-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Carbazolothiophene-2-carboxylic acid derivatives as endothelin receptor antagonists

  摘要：

  The SmI2-promoted three-component coupling reaction of thiophene-2-carboxylate, indole-2-carbaldehyde and acetophenone provides an expedient route to a series of tetracyclic carbazolothiophene compounds bearing the indole and thiophene rings. Among these samples, 9-benzyl-4-methyl-4-(4-hydroxyphenyl)-10-oxo-4,10-dihydrocarbazolo[2,3-b]thiophene-2-carboxylic acid (18) shows the most potent inhibition against the endothelin-1 induced increase of intracellular calcium ion concentration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.067