(S)-3-((S)-2-nitro-1-phenylethyl)-3-phenylindolin-2-one

• 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: (S)-3-((S)-2-nitro-1-phenylethyl)-3-phenylindolin-2-one
• 英文别名: (3S)-3-[(1S)-2-nitro-1-phenylethyl]-3-phenyl-1H-indol-2-one
• 化学式: C₂₂H₁₈N₂O₃
• 分子量: 358.397
• InChiKey: AASTUBXZIBSCMS-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-((S)-2-nitro-1-phenylethyl)-3-phenylindolin-2-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 nickel dichloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-(2-((3S,4S)-2-oxo-3,4-diphenylpyrrolidin-3-yl)phenyl)acetamide
  参考文献：
  名称：

  Synthesis of Lactams by Isomerization of Oxindoles Substituted at C-3 by an ω-Amino Chain

  摘要：

  Oxindoles substituted at N-1 by electron-withdrawing groups and at C-3 by omega-amino chains of various lengths undergo mild and easy isomerization to new 5- to 12-membered lactams in good yields (3096%). As efficient asymmetric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization provides a new and valuable access to medium-sized lactams alpha-substituted with a quaternary asymmetric carbon bearing a 2-aminophenyl residue.

  DOI：

  10.1021/jo501978j
• 作为产物：
  描述：

  β-硝基苯乙烯 、 3-苯基氧化吲哚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (R)-3-((S)-2-nitro-1-phenylethyl)-3-phenylindolin-2-one 、 (S)-3-((S)-2-nitro-1-phenylethyl)-3-phenylindolin-2-one
  参考文献：
  名称：

  未保护的3-取代的羟吲哚到硝基烯烃的有机催化迈克尔加成反应†

  摘要：

  奎尼丁业已发现以高产率和中等至良好的非对映选择性催化将未保护的3-取代的羟吲哚的迈克尔加成到硝基烯烃上。双功能奎尼丁 衍生的 硫脲催化剂10可以催化该反应以提供最多85％ee的主要非对映异构体。

  DOI：

  10.1039/c004037a

文献信息

• Chiral Bifunctional Thiosquaramides as Organocatalysts in the Synthesis of Enantioenriched 3,3-Disubstituted Oxindoles
  作者：Patricia Rodríguez-Ferrer、Daniel Naharro、Alicia Maestro、José M. Andrés、Rafael Pedrosa

  DOI：10.1002/ejoc.201901327

  日期：2019.10.17

  Four novel chiral bifunctional thiosquaramides have been prepared from cyclopentyl dithiosquarates and diamines derived from natural l‐valine and l‐tert‐leucine. The novel thiosquaramides have been tested as organocatalyst in the nitro‐Michael addition of 3‐substituted oxindoles to different β‐aryl‐substituted nitroalkenes. The reaction occurred easily in high yields and excellent stereoselectivities

  从环戊基二硫代方酸和天然l-缬氨酸和l-叔亮氨酸衍生的二胺制备了四种新型手性双官能硫代方酸酰胺。在将3-取代的羟吲哚的硝基-迈克尔加成到不同的β-芳基取代的硝基烯烃中作为有机催化剂时，已经测试了新型的硫代四氢呋喃酰胺。该反应容易以高收率和优异的立体选择性发生。
• Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins
  作者：Miao Ding、Feng Zhou、Zi-Qing Qian、Jian Zhou

  DOI：10.1039/c004037a

  日期：——

  Quinidine was found to catalyze the Michael addition of unprotected 3-substituted oxindoles to nitroolefins in excellent yield and moderate to good diastereoselectivity. Bifunctional quinidine derived thiourea catalyst 10 could catalyze this reaction to afford the major diastereomer in up to 85% ee.

  奎尼丁业已发现以高产率和中等至良好的非对映选择性催化将未保护的3-取代的羟吲哚的迈克尔加成到硝基烯烃上。双功能奎尼丁 衍生的 硫脲催化剂10可以催化该反应以提供最多85％ee的主要非对映异构体。
• Synthesis of Lactams by Isomerization of Oxindoles Substituted at C-3 by an ω-Amino Chain
  作者：Daad Sarraf、Nicolas Richy、Joëlle Vidal

  DOI：10.1021/jo501978j

  日期：2014.11.21

  Oxindoles substituted at N-1 by electron-withdrawing groups and at C-3 by omega-amino chains of various lengths undergo mild and easy isomerization to new 5- to 12-membered lactams in good yields (3096%). As efficient asymmetric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization provides a new and valuable access to medium-sized lactams alpha-substituted with a quaternary asymmetric carbon bearing a 2-aminophenyl residue.