(2'R,3'R)-ethyl 7-bromo-1-methyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate | 1345838-19-8

• 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: (2'R,3'R)-ethyl 7-bromo-1-methyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate
• 英文别名: ethyl (2'R,3R)-7-bromo-1-methyl-2-oxospiro[indole-3,3'-oxirane]-2'-carboxylate
• CAS: 1345838-19-8
• 化学式: C₁₃H₁₂BrNO₄
• 分子量: 326.147
• InChiKey: GEPPQOHDSMUVEQ-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-溴-1-甲基二氢吲哚-2,3-二酮 在 叔丁基过氧化氢 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 potassium carbonate 作用下， 以 四氢呋喃 、 癸烷 、 正己烷 、 水 为溶剂， 反应 48.0h， 生成 (2'S,3'R)-ethyl 7-bromo-1-methyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate 、 (2'S,3'S)-ethyl 7-bromo-1-methyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate 、 (2'R,3'R)-ethyl 7-bromo-1-methyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate 、 (2'R,3'S)-ethyl 7-bromo-1-methyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate
  参考文献：
  名称：

  Noncovalent Organocatalysis: A Powerful Tool for the Nucleophilic Epoxidation of α-Ylideneoxindoles

  摘要：

  A novel asymmetric nucleophilic epoxidation for alpha-ylideneoxindole esters has been successfully devised, resulting in enantioenriched spiro compounds with two new contiguous stereocenters. The employed (S)-alpha,alpha-diphenylprolinol functions as a bifunctional catalyst, creating a complex H-bond network in conjunction with a substrate and an oxidant.

  DOI：

  10.1021/ol202646w

文献信息

• Noncovalent Organocatalysis: A Powerful Tool for the Nucleophilic Epoxidation of α-Ylideneoxindoles
  作者：Chiara Palumbo、Giuseppe Mazzeo、Andrea Mazziotta、Augusto Gambacorta、M. Antonietta Loreto、Antonella Migliorini、Stefano Superchi、Daniela Tofani、Tecla Gasperi

  DOI：10.1021/ol202646w

  日期：2011.12.2

  A novel asymmetric nucleophilic epoxidation for alpha-ylideneoxindole esters has been successfully devised, resulting in enantioenriched spiro compounds with two new contiguous stereocenters. The employed (S)-alpha,alpha-diphenylprolinol functions as a bifunctional catalyst, creating a complex H-bond network in conjunction with a substrate and an oxidant.