(R_S,S)-N-[(1-phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide | 955942-03-7

• 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_S,S)-N-[(1-phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide
• 英文别名: (R)-N-[(S)-[1-(benzenesulfonyl)-4-nitroindol-2-yl]-(4-chlorophenyl)methyl]-2-methylpropane-2-sulfinamide
• CAS: 955942-03-7
• 化学式: C₂₅H₂₄ClN₃O₅S₂
• 分子量: 546.068
• InChiKey: BTBWUZMITVADDE-BHNGRWRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R_S,S)-N-[(1-phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide 、 对甲苯磺酰氯 在 盐酸 、 甲醇 、 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以98%的产率得到(S)-N-[(1-phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)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：

  4-nitro-1-(phenylsulfonyl)-1H-indole 、 (R)-N-(p-chlorobenzylidene)-tert-butanesulfinamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以77%的产率得到(R_S,S)-N-[(1-phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide
  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

• Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives
  作者：Liang Cheng、Li Liu、Yong Sui、Dong Wang、Yong-Jun Chen

  DOI：10.1016/j.tetasy.2007.07.029

  日期：2007.8

  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.