(S_S,R)-N-(p-toluenesulfinyl)-1,3-diphenylprop-2-ynylamine | 957061-24-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S_S,R)-N-(p-toluenesulfinyl)-1,3-diphenylprop-2-ynylamine
• 英文别名: (S)-N-[(1R)-1,3-diphenylprop-2-ynyl]-4-methylbenzenesulfinamide
• CAS: 957061-24-4
• 化学式: C₂₂H₁₉NOS
• 分子量: 345.465
• InChiKey: BEGNIWYZAZVIEN-DHLKQENFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S_S,R)-N-(p-toluenesulfinyl)-1,3-diphenylprop-2-ynylamine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1R)-1,3-diphenylprop-2-yn-1-amine
  参考文献：
  名称：

  Diastereoselective Alkynylation of N-p-Tolylsulfinylimines with Aluminum Acetylides

  摘要：

  The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.

  DOI：

  10.1021/jo071139w
• 作为产物：
  描述：

  (phenylethynyl)dimethylaluminum 、 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到(S_S,R)-N-(p-toluenesulfinyl)-1,3-diphenylprop-2-ynylamine
  参考文献：
  名称：

  Diastereoselective Alkynylation of N-p-Tolylsulfinylimines with Aluminum Acetylides

  摘要：

  The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.

  DOI：

  10.1021/jo071139w

文献信息

• Diastereoselective Alkynylation of <i>N</i>-<i>p</i>-Tolylsulfinylimines with Aluminum Acetylides
  作者：Serge Turcaud、Farouk Berhal、Jacques Royer

  DOI：10.1021/jo071139w

  日期：2007.10.1

  The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.