1-phenyl-3,3a,4,5-tetrahydro-1H-indole-2,6-dione | 1020661-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-phenyl-3,3a,4,5-tetrahydro-1H-indole-2,6-dione
• 英文别名: 1-Phenyl-3,3a,4,5-tetrahydroindole-2,6-dione；1-phenyl-3,3a,4,5-tetrahydroindole-2,6-dione
• CAS: 1020661-18-0
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: RCBKKFQHOWPQKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-phenyl-2-(1,4,8,11-tetraoxadispiro[4.1.4.3]tetradec-12-yl)acetamide 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以78%的产率得到1-phenyl-3,3a,4,5-tetrahydro-1H-indole-2,6-dione
  参考文献：
  名称：

  乙缩醛保护的（2,4-Dioxocyclohex-1-yl）乙酰胺的酸催化环化反应合成2,6-二氧-1,2,3,4,5,6-六氢吲哚并将其转化为5,8， 9,10-四氢-6 H-吲哚并[2,1- a ]异喹啉-9-一

  摘要：

  Abstractmagnified imageAcetal‐protected (2,4‐dioxocyclohex‐1‐yl)acetic acids were prepared by allylation of dilithiated 1,3‐cyclohexane‐1,3‐diones, protection of the carbonyl groups and oxidation of the alkene moiety. Their reaction with amines afforded the corresponding amides which were transformed, by acid‐catalyzed cyclization, into various 2,6‐dioxo‐1,2,3,4,5,6‐hexahydroindoles. The reaction of the latter with triflic acid resulted in the formation of novel 5,8,9,10‐tetrahydro‐6H‐indolo[2,1‐a]isoquinolin‐9‐ones.

  DOI：

  10.1002/adsc.200800691

文献信息

• Efficient synthesis of 2,6-dioxo-1,2,3,4,5,6-hexahydroindoles based on the synthesis and reactions of (2,4-dioxocyclohex-1-yl)acetic acid derivatives
  作者：Benard Juma、Muhammad Adeel、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tetlet.2008.02.027

  日期：2008.3

  Acetal-protected (2,.4-dioxocyclohex-1-yl)acetic acid derivatives were prepared by the allylation of dilithiated 1,3-cyclohexane-1,3-diones, by the protection of the carbonyl groups and by the oxidation of the alkene. The products were then transformed, by amide formation and subsequent cyclization, into 2,6-dioxo-1,2,3,4,5,6-hexahydroindoles, which represent important intermediates for the synthesis of various alkaloids. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 2,6-Dioxo-1,2,3,4,5,6-hexahydroindoles by Acid- Catalyzed Cyclization of Acetal-Protected (2,4-Dioxocyclohex-1-yl)acetamides and their Transformation into 5,8,9,10-Tetrahydro-6<i>H</i>-indolo[2,1-<i>a</i>]isoquinolin-9-ones
  作者：Benard Juma、Muhammad Adeel、Alexander Villinger、Helmut Reinke、Anke Spannenberg、Christine Fischer、Peter Langer

  DOI：10.1002/adsc.200800691

  日期：2009.5

  Abstractmagnified imageAcetal‐protected (2,4‐dioxocyclohex‐1‐yl)acetic acids were prepared by allylation of dilithiated 1,3‐cyclohexane‐1,3‐diones, protection of the carbonyl groups and oxidation of the alkene moiety. Their reaction with amines afforded the corresponding amides which were transformed, by acid‐catalyzed cyclization, into various 2,6‐dioxo‐1,2,3,4,5,6‐hexahydroindoles. The reaction of the latter with triflic acid resulted in the formation of novel 5,8,9,10‐tetrahydro‐6H‐indolo[2,1‐a]isoquinolin‐9‐ones.