1'-benzyl-1,2,3,11b-tetrahydrospiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1'-benzyl-1,2,3,11b-tetrahydrospiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione
• 英文别名: (11R,16S)-1'-benzylspiro[15-azatetracyclo[8.6.0.03,8.011,15]hexadeca-1(10),3,5,7-tetraene-16,3'-indole]-2,2',9-trione
• 化学式: C₂₉H₂₂N₂O₃
• 分子量: 446.505
• InChiKey: KOBVAOKRAXQZDQ-BTYSJIOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-苄基-1H-吲哚-2,3-二酮 、 DL-脯氨酸 、 1,4-萘醌 以 水 、 乙酸乙酯 为溶剂， 反应 0.33h， 以93%的产率得到1'-benzyl-1,2,3,11b-tetrahydrospiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione
  参考文献：
  名称：

  Ethyl lactate as a promising bio based green solvent for the synthesis of spiro-oxindole derivatives via 1,3-dipolar cycloaddition reaction

  摘要：

  Ethyl lactate as a bio based green solvent was used, for the first time to promote the 1,3-dipolar cyclo-addition reaction of azomethine ylide generated in situ by the decarboxylative condensation of substituted isatin and proline with napthoquinone as dipolarophile, which generates a series of medicinally privileged spiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione derivatives in excellent yields at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.035

文献信息

• Facile Three-Component Synthesis of Spirooxindolepyrrololine Ring Systems via 1,3-Dipolar Cycloaddition with 1,4-Naphthoquinone
  作者：Hua Chen、Shun-Yi Wang、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1080/00397911.2010.517413

  日期：2011.11.15

  1,3-Dipolar cycloadditions involving 1,4-naphthoquinone and an azomethine ylide generated from a-amino acids and isatins have been used in this reaction to afford the pyrrolidine-2-spiro-3'-oxindole 4 or 5 with moderate to excellent yields.
• Ethyl lactate as a promising bio based green solvent for the synthesis of spiro-oxindole derivatives via 1,3-dipolar cycloaddition reaction
  作者：Anshu Dandia、Anuj K. Jain、Ashok K. Laxkar

  DOI：10.1016/j.tetlet.2013.05.035

  日期：2013.7

  Ethyl lactate as a bio based green solvent was used, for the first time to promote the 1,3-dipolar cyclo-addition reaction of azomethine ylide generated in situ by the decarboxylative condensation of substituted isatin and proline with napthoquinone as dipolarophile, which generates a series of medicinally privileged spiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione derivatives in excellent yields at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.