(S)-N,N-1,2-benzenedisulfonyl-1-phenylethylamine | 209863-91-2

• 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: (S)-N,N-1,2-benzenedisulfonyl-1-phenylethylamine
• 英文别名: 2-[(1S)-1-phenylethyl]-1lambda6,3lambda6,2-benzodithiazole 1,1,3,3-tetraoxide；2-[(1S)-1-phenylethyl]-1λ6,3λ6,2-benzodithiazole 1,1,3,3-tetraoxide
• CAS: 209863-91-2
• 化学式: C₁₄H₁₃NO₄S₂
• 分子量: 323.394
• InChiKey: MDMHRTQZDRTCPP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N,N-1,2-benzenedisulfonyl-1-phenylethylamine 在 potassium nitrite 、 18-冠醚-6 、 N,N-二甲基甲酰胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (S)-(-)-1-苯乙醇 、 (R)-(+)-1-苯基乙醇
  参考文献：
  名称：

  N , N -1,2-Benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines

  摘要：

  We hereby report the preparation and nucleophilic substitutions of the N,N-1,2-benzenedisulfonylimide derivatives la and 2a of the chiral amines 1 and 2. The nucleophilic attack of KNO2 afforded the respective alcohols 3 and 4 with 84-90% inversion of configuration. Nucleophilic attack by the azide ion afforded the azide products 5 and 6 which were reduced to the corresponding inverted amines 1 and 2 (94-98.5% inversion). The improved leaving group ability of the N,N-1,2-benzenedisulfonylimides compared with previously reported N,N-disulfonylimides is discussed. Chiral GLC analysis of all products is summarized and the alternative chiral analysis of product 3 by C-13 NMR using heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin as a chiral solvating agent (CSA) is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00033-0
• 作为产物：
  描述：

  2-sulfo-benzenediazonium-betaine 在 盐酸 、 五氯化磷 、 二氧化硫 、 溶剂黄146 、 三乙胺 、 copper(l) chloride 、 sodium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-N,N-1,2-benzenedisulfonyl-1-phenylethylamine
  参考文献：
  名称：

  N , N -1,2-Benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines

  摘要：

  We hereby report the preparation and nucleophilic substitutions of the N,N-1,2-benzenedisulfonylimide derivatives la and 2a of the chiral amines 1 and 2. The nucleophilic attack of KNO2 afforded the respective alcohols 3 and 4 with 84-90% inversion of configuration. Nucleophilic attack by the azide ion afforded the azide products 5 and 6 which were reduced to the corresponding inverted amines 1 and 2 (94-98.5% inversion). The improved leaving group ability of the N,N-1,2-benzenedisulfonylimides compared with previously reported N,N-disulfonylimides is discussed. Chiral GLC analysis of all products is summarized and the alternative chiral analysis of product 3 by C-13 NMR using heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin as a chiral solvating agent (CSA) is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00033-0

文献信息

• Formation of chiral aryl ethers from enantiopure amine or alcohol substrates
  作者：Sadri A. Said、Anne Fiksdahl

  DOI：10.1016/s0957-4166(01)00130-6

  日期：2001.4

  Three methods for the preparation of chiral aryl ethers are demonstrated. N,N-Disulfonylimide derivatives are used in the stereoselective formation of aryl ethers from chiral amines. Nucleophilic attack of aryloxide anions on the cyclic N,N-disulfonylimide derivative of (S)-1-phenylethylamine afforded the (R)-1-phenylethyl phenyl and 2-naphthyl ethers with 83-87 and 70-79% inversion of configuration, respectively. The results are compared with results from alternative methods for the preparation of homochiral aryl ethers from chiral alcohols with complete retention and inversion of configuration, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.