(S)-4-methyl-N-[(1S)-1-phenylpentyl]benzenesulfinamide | 131154-13-7

• 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: (S)-4-methyl-N-[(1S)-1-phenylpentyl]benzenesulfinamide
• CAS: 131154-13-7
• 化学式: C₁₈H₂₃NOS
• 分子量: 301.453
• InChiKey: IBEMJRSTAYHVOV-RXVVDRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-4-methyl-N-[(1S)-1-phenylpentyl]benzenesulfinamide 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到(1S)-1-phenyl-1-pentanamine
  参考文献：
  名称：

  Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

  摘要：

  Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

  DOI：

  10.1021/jo00001a003
• 作为产物：
  描述：

  (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-4-methyl-N-[(1S)-1-phenylpentyl]benzenesulfinamide
  参考文献：
  名称：

  Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

  摘要：

  Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

  DOI：

  10.1021/jo00001a003

文献信息

• Stereoselective addition to chiral p-toluene sulfinimines
  作者：Wing Hong Chan、Albert W.M Lee、Ping Fang Xia、Wai Yeung Wong

  DOI：10.1016/s0040-4039(00)00949-7

  日期：2000.7

  Diastereoselective addition of a number of Grignard reagents to chiral p-toluene sulfinimines 2b–2d under the mediation of copper salts afforded various protected α-branched amines.

  在铜盐的介导下，向手性对甲苯磺胺亚胺2b - 2d非对映选择性地添加了许多格氏试剂，得到了各种受保护的α-支化胺。