1-Methyl-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-2,2',5'-trione | 1181785-28-3

• 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: 1-Methyl-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-2,2',5'-trione
• CAS: 1181785-28-3
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: GIGXFVCJKZLRMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methyl-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-2,2',5'-trione 、 苯基溴化镁 以 二氯甲烷 为溶剂， 以18%的产率得到
  参考文献：
  名称：

  Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates

  摘要：

  Two efficient and rapid accesses to spiro-oxindole entities bearing an imide function were presented, and their performance was compared. The key components are N-substituted alpha-bromoacetamides to reach these derivatives in tandem process. The resulting spiro-imides from these methodologies were regioselectively reduced into corresponding N-acyliminium precursors, which were subsequently submitted to an intramolecular cyclization to provide pentacyclic spiro-oxindole architecture analogues to pteropodine and spirotryprostatin-B alkaloids with high diastereoselective control. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.114
• 作为产物：
  描述：

  2-溴-N-(2-苯乙基)乙酰胺 、 ethyl 1-methyl-2-oxoindoline-3-carboxylate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到1-Methyl-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-2,2',5'-trione
  参考文献：
  名称：

  Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates

  摘要：

  Two efficient and rapid accesses to spiro-oxindole entities bearing an imide function were presented, and their performance was compared. The key components are N-substituted alpha-bromoacetamides to reach these derivatives in tandem process. The resulting spiro-imides from these methodologies were regioselectively reduced into corresponding N-acyliminium precursors, which were subsequently submitted to an intramolecular cyclization to provide pentacyclic spiro-oxindole architecture analogues to pteropodine and spirotryprostatin-B alkaloids with high diastereoselective control. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.114

文献信息

• Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates
  作者：Iyad Allous、Sébastien Comesse、Dušan Berkeš、Amar Alkyat、Adam Daïch

  DOI：10.1016/j.tetlet.2009.02.114

  日期：2009.8

  Two efficient and rapid accesses to spiro-oxindole entities bearing an imide function were presented, and their performance was compared. The key components are N-substituted alpha-bromoacetamides to reach these derivatives in tandem process. The resulting spiro-imides from these methodologies were regioselectively reduced into corresponding N-acyliminium precursors, which were subsequently submitted to an intramolecular cyclization to provide pentacyclic spiro-oxindole architecture analogues to pteropodine and spirotryprostatin-B alkaloids with high diastereoselective control. (C) 2009 Elsevier Ltd. All rights reserved.