N-(2-(1H-indol-3-yl)ethyl)-4-oxopent-2-enamide

• 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: N-(2-(1H-indol-3-yl)ethyl)-4-oxopent-2-enamide
• 英文别名: (E)-N-[2-(1H-indol-3-yl)ethyl]-4-oxopent-2-enamide
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: PPGNBOZTOVFSPR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)-4-oxopent-2-enamide 以 甲醇 为溶剂， 以95%的产率得到5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-methyl-1,5-dihydropyrrol-2-one
  参考文献：
  名称：

  Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α,β-unsaturated amides

  摘要：

  Photolysis of gamma-keto-alpha,beta-unsaturated amides provides N-alkyl pyrrolidinones in high yield (77-100%). The procedure is applicable to a variety of amides derived from the corresponding gamma-keto acid.

  DOI：

  10.1016/0040-4039(95)00779-c
• 作为产物：
  描述：

  色胺 、 (E)-4-氧代-2-烯酸 在 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到N-(2-(1H-indol-3-yl)ethyl)-4-oxopent-2-enamide
  参考文献：
  名称：

  Synthesis of the polycyclic core of vincorine via cascade reactions

  摘要：

  We developed a six-step synthesis of the polycyclic core of vincorine using two cascades of reactions. A cascade of Michael-Mannich reactions was employed for one-pot preparation of a polycyclic intermediate, which was transformed into the desired polycyclic pyrroloindoline ring system using a cascade of methanolysis-N-imine cyclization reactions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.028

文献信息

• Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α,β-unsaturated amides
  作者：James P. Dittami、Feng Xu、Hua Qi、Matthew W. Martin、Jon Bordner、Debra L. Decosta、Jeffrey Kiplinger、Philip Reiche、Richard Ware

  DOI：10.1016/0040-4039(95)00779-c

  日期：1995.6

  Photolysis of gamma-keto-alpha,beta-unsaturated amides provides N-alkyl pyrrolidinones in high yield (77-100%). The procedure is applicable to a variety of amides derived from the corresponding gamma-keto acid.
• Synthesis of the polycyclic core of vincorine via cascade reactions
  作者：Zhi-Wei Zhang、Jiong Yang

  DOI：10.1016/j.tetlet.2013.12.028

  日期：2014.1

  We developed a six-step synthesis of the polycyclic core of vincorine using two cascades of reactions. A cascade of Michael-Mannich reactions was employed for one-pot preparation of a polycyclic intermediate, which was transformed into the desired polycyclic pyrroloindoline ring system using a cascade of methanolysis-N-imine cyclization reactions. (C) 2013 Elsevier Ltd. All rights reserved.