(2R,3S,5aS,10aS)-5'-fluoro-3-(4-methoxyphenyl)-5a,6,7,8-tetrahydro-1H,5H-spiro[dipyrrolo[1,2-a:1',2'-d]pyrazine-2,3'-indole]-2',5,10(1'H,10aH)-trione | 1352401-86-5

• 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: (2R,3S,5aS,10aS)-5'-fluoro-3-(4-methoxyphenyl)-5a,6,7,8-tetrahydro-1H,5H-spiro[dipyrrolo[1,2-a:1',2'-d]pyrazine-2,3'-indole]-2',5,10(1'H,10aH)-trione
• 英文别名: (3S,5R,6S,9S)-5'-fluoro-6-(4-methoxyphenyl)spiro[1,7-diazatricyclo[7.3.0.03,7]dodecane-5,3'-1H-indole]-2,2',8-trione
• CAS: 1352401-86-5
• 化学式: C₂₄H₂₂FN₃O₄
• 分子量: 435.455
• InChiKey: DUMXRFAJXHSRAS-AZXNSQLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甘氨酸,N-[(4-甲氧苯基)亚甲基]-,甲基酯 在 哌啶 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 (Rp)-2-(tert-butylthio)-1-(diphenylphosphino)ferrocene 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成 (2R,3S,5aS,10aS)-5'-fluoro-3-(4-methoxyphenyl)-5a,6,7,8-tetrahydro-1H,5H-spiro[dipyrrolo[1,2-a:1',2'-d]pyrazine-2,3'-indole]-2',5,10(1'H,10aH)-trione
  参考文献：
  名称：

  Enantioselective synthesis of the spirotryprostatin A scaffold

  摘要：

  The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex 3,3'-pyrrolidinyl-spirooxindole core with Fmoc-proline and spontaneous ring closure upon N-deprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.056

文献信息

• Enantioselective synthesis of the spirotryprostatin A scaffold
  作者：Andrey P. Antonchick、Hannah Schuster、Hanna Bruss、Markus Schürmann、Hans Preut、Daniel Rauh、Herbert Waldmann

  DOI：10.1016/j.tet.2011.04.056

  日期：2011.12

  The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex 3,3'-pyrrolidinyl-spirooxindole core with Fmoc-proline and spontaneous ring closure upon N-deprotection. (C) 2011 Elsevier Ltd. All rights reserved.