(R,E)-N-(4-nitrobenzylidene)-2-methylpropane-2-sulfinamide | 736946-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,E)-N-(4-nitrobenzylidene)-2-methylpropane-2-sulfinamide
• 英文别名: (NE,R)-2-methyl-N-[(4-nitrophenyl)methylidene]propane-2-sulfinamide
• CAS: 736946-87-5
• 化学式: C₁₁H₁₄N₂O₃S
• 分子量: 254.31
• InChiKey: XNQNNFJWRGXIFE-FWVUHSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,E)-N-(4-nitrobenzylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 甲醇 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 3.0h， 生成 (S)-N-[(1-phenylsulfonyl-1H-indol-2-yl)(p-nitrophenyl)methyl]-p-toluenesulfonamide
  参考文献：
  名称：

  Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives

  摘要：

  Nucleophilic addition reactions of 2-lithiated N-phenylsulfonylindoles with (R)-N-tert-butanesulfinyl aldimines provided chiral (2-indolyl) methanamine derivatives in moderate to good yields (up to 100%) with excellent diastereoselectivities (>99: 1), in which no additional Lewis acids were required. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.029
• 作为产物：
  描述：

  对硝基苯甲醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(R,E)-N-(4-nitrobenzylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives

  摘要：

  Nucleophilic addition reactions of 2-lithiated N-phenylsulfonylindoles with (R)-N-tert-butanesulfinyl aldimines provided chiral (2-indolyl) methanamine derivatives in moderate to good yields (up to 100%) with excellent diastereoselectivities (>99: 1), in which no additional Lewis acids were required. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.029

文献信息

• Efficient Trapping of Oxonium Ylides with Imines: A Highly Diastereoselective Three-Component Reaction for the Synthesis of β-Amino-α-hydroxyesters with Quaternary Stereocenters
  作者：Haoxi Huang、Xin Guo、Wenhao Hu

  DOI：10.1002/anie.200604389

  日期：2007.2.12
• A Convenient Synthesis of Chiral Nonracemic Vinyl Aziridines
  作者：Daniel Morton、David Pearson、Robert A. Field、Robert A. Stockman

  DOI：10.1021/ol049252l

  日期：2004.7.1

  The preparation of a range of alkyl and aryl chiral vinyl aziridines was achieved in high yield and stereoselectivity, and with excellent diastereoselectivity, by reaction of tert-butylsulfinylimines with the ylide derived from S-allyl tetrahydrothiophenium bromide.