2-methyl-N-((E,S)-{2-[(4-methylphenyl)sulfinyl]phenyl}methylene)propan-1-amine | 949146-68-3

• 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: 2-methyl-N-((E,S)-{2-[(4-methylphenyl)sulfinyl]phenyl}methylene)propan-1-amine
• CAS: 949146-68-3
• 化学式: C₁₈H₂₁NOS
• 分子量: 299.437
• InChiKey: IODZPQBFXANVCB-YMFQVDJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methyl-N-((E,S)-{2-[(4-methylphenyl)sulfinyl]phenyl}methylene)propan-1-amine 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.17h， 生成 2-methyl-N-((E,S)-1-{2-[(4-methylphenyl)sulfinyl]phenyl}ethylidene)propan-1-amine
  参考文献：
  名称：

  Stereoselective Quaternization of α-Amino Phenylacetonitriles Mediated by a Remote Sulfinyl Group

  摘要：

  Enantiomerically pure alpha-substituted alpha-amino phenylacetonitriles have been readily prepared from 2-p-tolylsulfinylbenzaldimines following a two-step sequence: a moderately stereoselective hydrocyanation of the imines and a completely stereoselective quaternization of the resulting diastereoisomeric mixture of alpha-amino phenylacetonitriles with different alkylating or acylating reagents in the presence of KHMDS. Theoretical calculations support a stereoselectivity control exerted by the remote sulfinyl group, as long as it is responsible for the conformational preferences of the benzyllithium intermediates, which suffer the attack of the electrophiles to the less hindered diastereotopic face.

  DOI：

  10.1021/jo0705519
• 作为产物：
  描述：

  (S)-2-(p-tolylsulfinyl)benzaldehyde 、 异丁胺 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到2-methyl-N-((E,S)-{2-[(4-methylphenyl)sulfinyl]phenyl}methylene)propan-1-amine
  参考文献：
  名称：

  Stereoselective Quaternization of α-Amino Phenylacetonitriles Mediated by a Remote Sulfinyl Group

  摘要：

  Enantiomerically pure alpha-substituted alpha-amino phenylacetonitriles have been readily prepared from 2-p-tolylsulfinylbenzaldimines following a two-step sequence: a moderately stereoselective hydrocyanation of the imines and a completely stereoselective quaternization of the resulting diastereoisomeric mixture of alpha-amino phenylacetonitriles with different alkylating or acylating reagents in the presence of KHMDS. Theoretical calculations support a stereoselectivity control exerted by the remote sulfinyl group, as long as it is responsible for the conformational preferences of the benzyllithium intermediates, which suffer the attack of the electrophiles to the less hindered diastereotopic face.

  DOI：

  10.1021/jo0705519