3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(1H-indol-3-yl)propionic acid | 307002-15-9

• 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: 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(1H-indol-3-yl)propionic acid
• 英文别名: 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(1H-indol-3-yl)propanoic acid
• CAS: 307002-15-9
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: BEGZCBJXFJRSBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(1H-indol-3-yl)propionic acid 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 4-(1H-indol-3-yl)-2,6-dioxooxane-3-carboxylic acid
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3
• 作为产物：
  描述：

  benzyl 3-[2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl]-3-(1H-indol-3-yl)propanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 20.0h， 以79%的产率得到3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(1H-indol-3-yl)propionic acid
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

文献信息

• A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives
  作者：Michel Boisbrun、Laurent Jeannin、Loïc Toupet、Jean-Yves Laronze

  DOI：10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

  日期：2000.9

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.