5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-methyl-1,5-dihydropyrrol-2-one | 169170-59-6

• 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: 5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-methyl-1,5-dihydropyrrol-2-one
• 英文别名: 5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-methylpyrrol-2-one
• CAS: 169170-59-6
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: SSNPYPJZFCGZDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-methyl-1,5-dihydropyrrol-2-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 11b-Methyl-5,6,11,11b-tetrahydro-indolizino[8,7-b]indol-3-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：

  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

文献信息

• Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams:  H-Bond Donor Catalysis by Anion Binding
  作者：Izzat T. Raheem、Parvinder S. Thiara、Emily A. Peterson、Eric N. Jacobsen

  DOI：10.1021/ja076179w

  日期：2007.11.1

  indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiourea.

  在硫脲催化的色胺衍生的羟基内酰胺的环化中获得高度对映体富集的吲哚嗪酮和喹嗪酮产物。取代基和反离子效应研究指出了一种新的催化机制，涉及限速阴离子提取和硫脲结合。
• 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.