(2'R,3'S,4'R,5'R)-6-Chloro-2'-(2,2-dimethyl-propyl)-1'-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-2-oxo-4'-thiophen-2-yl-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid dimethylamide | 865080-05-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2'R,3'S,4'R,5'R)-6-Chloro-2'-(2,2-dimethyl-propyl)-1'-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-2-oxo-4'-thiophen-2-yl-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid dimethylamide
• 英文别名: (2'R,3S,3'R,5'R)-6-chloro-5'-(2,2-dimethylpropyl)-1'-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-N,N-dimethyl-2-oxo-3'-thiophen-2-ylspiro[1H-indole-3,4'-pyrrolidine]-2'-carboxamide
• CAS: 865080-05-3
• 化学式: C₃₇H₄₀ClN₃O₃S
• 分子量: 642.262
• InChiKey: KHHGCYAEVLDMBN-MLMHKPGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2'R,3'S,4'R,5'R)-6-Chloro-2'-(2,2-dimethyl-propyl)-1'-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-2-oxo-4'-thiophen-2-yl-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid dimethylamide 在 lead(IV) acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以63%的产率得到(2'R,3S,4'R,5'R)-6-chloro-2'-(2,2-dimethyl-propyl)-2-oxo-4'-thiophen-2-yl-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid dimethylamide
  参考文献：
  名称：

  Synthesis of spirooxindoles via asymmetric 1,3-dipolar cycloaddition

  摘要：

  An efficient method was developed for the asymmetric synthesis of 2'-alkyl-4'aryl-1H-spiro[indole-3,3'-pyrrolidin]-2-ones, which are potential inhibitors of the p53-MDM2 interaction. Our X-ray crystallographic analysis revealed that this 1,3-dipolar cycloaddition proceeds with high stereoselectivity but differently from previously published results. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.114
• 作为产物：
  描述：

  6-氯氧化吲哚 在 哌嗪 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 (2'R,3'S,4'R,5'R)-6-Chloro-2'-(2,2-dimethyl-propyl)-1'-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-2-oxo-4'-thiophen-2-yl-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid dimethylamide
  参考文献：
  名称：

  Synthesis of spirooxindoles via asymmetric 1,3-dipolar cycloaddition

  摘要：

  An efficient method was developed for the asymmetric synthesis of 2'-alkyl-4'aryl-1H-spiro[indole-3,3'-pyrrolidin]-2-ones, which are potential inhibitors of the p53-MDM2 interaction. Our X-ray crystallographic analysis revealed that this 1,3-dipolar cycloaddition proceeds with high stereoselectivity but differently from previously published results. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.114