(E)-1-(3-methoxycarbonylindol-2-yl)-2-propen-1-one | 364078-92-2

• 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: (E)-1-(3-methoxycarbonylindol-2-yl)-2-propen-1-one
• 英文别名: methyl 2-prop-2-enoyl-1H-indole-3-carboxylate
• CAS: 364078-92-2
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: JVOXMMAQJGQKLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-methoxycarbonylindol-2-yl)-2-propen-1-one 以 均三甲苯 为溶剂， 反应 2.0h， 以17%的产率得到methyl 2,3-dihydro-1-oxo-1H-pyrrolo[1,2-a]indole-9-carboxylate
  参考文献：
  名称：

  Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole

  摘要：

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.

  DOI：

  10.3987/com-01-9230
• 作为产物：
  描述：

  [2-(1-benzenesulfonyl-3-carboxyindol-2-yl)-2-oxoethylidene]triphenylphosphorane 在 硫酸 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 (E)-1-(3-methoxycarbonylindol-2-yl)-2-propen-1-one
  参考文献：
  名称：

  Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole

  摘要：

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.

  DOI：

  10.3987/com-01-9230

文献信息

• Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole
  作者：Yasuyoshi Miki、Hiroko Hachiken、Atsuko Kawazoe、Yasuhiko Tsuzaki、Norihide Yanase

  DOI：10.3987/com-01-9230

  日期：——

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.