[2S,3S,S(R)]-N-[2-(4-methylphenyl)-3-phenyl-3-(methylsulfenyl)propyl]-p-toluenesulfinamide | 1093167-67-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [2S,3S,S(R)]-N-[2-(4-methylphenyl)-3-phenyl-3-(methylsulfenyl)propyl]-p-toluenesulfinamide
• 英文别名: (R)-4-methyl-N-[(1S,2S)-2-(4-methylphenyl)-1-methylsulfanyl-1-phenylpropan-2-yl]benzenesulfinamide
• CAS: 1093167-67-9
• 化学式: C₂₄H₂₇NOS₂
• 分子量: 409.616
• InChiKey: WEDGTASHFZHDJM-IBGGVINMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2S,3S,S(R)]-N-[2-(4-methylphenyl)-3-phenyl-3-(methylsulfenyl)propyl]-p-toluenesulfinamide 在 甲醇 、 三氟乙酸 、 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到(2S,3S)-2-(p-methylphenyl)-3-(methylsulfenyl)-3-phenyl-propan-2-amine
  参考文献：
  名称：

  Stereoselective Addition of α-Methylsulfenyl Benzyl Carbanions to N-Sulfinylketimines: Asymmetric Synthesis of α,α-Dibranched β-Sulfanyl Amines

  摘要：

  (R)- and (S)-N-sulfinylketimines react with the ortho-sulfinyl benzyl carbanion derived from (S)-1 affording epimeric mixtures at the benzylic carbon of alpha,alpha-dibranched beta-sulfanyl amines. The N-sulfinyl group completely controls the configuration at the quaternary carbon bonded to the nitrogen, whereas the C-sulfinyl group is responsible for the level of asymmetric induction. High stereoselectivity can be achieved when the configuration at the sulfur atoms of the reagents are opposite (matched pair). After a two-step desulfinylation process, this reaction provides a procedure for synthesizing diastereomerically pure syn-1,2-sulfanyl amines containing a chiral quaternary carbon adjacent to nitrogen.

  DOI：

  10.1021/jo802200f
• 作为产物：
  描述：

  [2S,3S,S(R)]-N-{2-(4-methylphenyl)-3-[(S)-2-(p-toluenesulfinyl)phenyl]-3-(methylsulfenyl)propyl}-p-toluenesulfinamide 在 叔丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以100%的产率得到[2S,3S,S(R)]-N-[2-(4-methylphenyl)-3-phenyl-3-(methylsulfenyl)propyl]-p-toluenesulfinamide
  参考文献：
  名称：

  Stereoselective Addition of α-Methylsulfenyl Benzyl Carbanions to N-Sulfinylketimines: Asymmetric Synthesis of α,α-Dibranched β-Sulfanyl Amines

  摘要：

  (R)- and (S)-N-sulfinylketimines react with the ortho-sulfinyl benzyl carbanion derived from (S)-1 affording epimeric mixtures at the benzylic carbon of alpha,alpha-dibranched beta-sulfanyl amines. The N-sulfinyl group completely controls the configuration at the quaternary carbon bonded to the nitrogen, whereas the C-sulfinyl group is responsible for the level of asymmetric induction. High stereoselectivity can be achieved when the configuration at the sulfur atoms of the reagents are opposite (matched pair). After a two-step desulfinylation process, this reaction provides a procedure for synthesizing diastereomerically pure syn-1,2-sulfanyl amines containing a chiral quaternary carbon adjacent to nitrogen.

  DOI：

  10.1021/jo802200f

文献信息

• Stereoselective Addition of α-Methylsulfenyl Benzyl Carbanions to <i>N</i>-Sulfinylketimines: Asymmetric Synthesis of α,α-Dibranched β-Sulfanyl Amines
  作者：Yolanda Arroyo、Ángela Meana、M. Ascensión Sanz-Tejedor、Inés Alonso、José L. García Ruano

  DOI：10.1021/jo802200f

  日期：2009.1.16

  (R)- and (S)-N-sulfinylketimines react with the ortho-sulfinyl benzyl carbanion derived from (S)-1 affording epimeric mixtures at the benzylic carbon of alpha,alpha-dibranched beta-sulfanyl amines. The N-sulfinyl group completely controls the configuration at the quaternary carbon bonded to the nitrogen, whereas the C-sulfinyl group is responsible for the level of asymmetric induction. High stereoselectivity can be achieved when the configuration at the sulfur atoms of the reagents are opposite (matched pair). After a two-step desulfinylation process, this reaction provides a procedure for synthesizing diastereomerically pure syn-1,2-sulfanyl amines containing a chiral quaternary carbon adjacent to nitrogen.