methyl (2'R,3R,5'S)-1'-acetyl-2'-(2,3-dichlorophenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate | 1352401-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2'R,3R,5'S)-1'-acetyl-2'-(2,3-dichlorophenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate
• 英文别名: methyl (2'S,3R,5'R)-1'-acetyl-5'-(2,3-dichlorophenyl)-2-oxospiro[1H-indole-3,4'-pyrrolidine]-2'-carboxylate
• CAS: 1352401-90-1
• 化学式: C₂₁H₁₈Cl₂N₂O₄
• 分子量: 433.291
• InChiKey: IJZDQKRRWVGORY-DJPFJPOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-亚甲基氧化吲哚 、 methyl 2-((2,3-dichlorobenzylidene)amino)acetate 在 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 2.0h， 生成 methyl (2'R,3R,5'S)-1'-acetyl-2'-(2,3-dichlorophenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate
  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.