5'-Hydroxy-1-methyl-1'-(2-phenylethyl)spiro[indole-3,4'-pyrrolidine]-2,2'-dione | 1181785-41-0

• 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-methyl-1'-(2-phenylethyl)spiro[indole-3,4'-pyrrolidine]-2,2'-dione
• CAS: 1181785-41-0
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: DXCYLKXEVBSLOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-Hydroxy-1-methyl-1'-(2-phenylethyl)spiro[indole-3,4'-pyrrolidine]-2,2'-dione 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以83%的产率得到(1R,10bS)-1'-methylspiro[2,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinoline-1,3'-indole]-2',3-dione
  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：

  1-Methyl-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-2,2',5'-trione 在 三乙基硼氢化锂 作用下， 以 二氯甲烷 为溶剂， 生成 5'-Hydroxy-1-methyl-1'-(2-phenylethyl)spiro[indole-3,4'-pyrrolidine]-2,2'-dione 、 5'-Hydroxy-1-methyl-1'-(2-phenylethyl)spiro[indole-3,3'-pyrrolidine]-2,2'-dione
  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.