N-(1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)prop-1-en-1-yl)-p-toluenesulfonamide | 1586870-17-8

• 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: N-(1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)prop-1-en-1-yl)-p-toluenesulfonamide
• CAS: 1586870-17-8
• 化学式: C₂₃H₃₃NO₃SSi
• 分子量: 431.671
• InChiKey: MKGVNJAEGULDMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-((E)-1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)allylidene)-p-toluenesulfonamide 在 正丁基锂 、 (S)-2,2-dimethyl-N-(2-(4-methylpiperazin-1-yl)-1-phenylethyl)propan-1-amine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以60%的产率得到(E)-N-(1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)allyl)-p-toluenesulfonamide
  参考文献：
  名称：

  Enantioselective Synthesis of α-Silylamines by Meerwein–Ponndorf–Verley-Type Reduction of α-Silylimines by a Chiral Lithium Amide

  摘要：

  Meerwein-Ponndorf-Verley-type reduction of N-tosylsilylimines with chiral lithium amide 2 affords alpha-silylamines in high enantioselectivity. Since the enantioselectivity observed was inconsistent with our previously proposed chairlike six-membered transition structure, we performed density functional theory (DFT) calculations on transition states leading to (S)- and (R)-7a and (S)- and (R)-7e using an N-phenylsulfonyl derivatives 12 and 13 as model systems. Results of the calculations showed that the structures are considerably deformed from the chairlike form with steric repulsions between the 1'-methylene group and the imine-carbon substituents playing an important role in the control of the, enantioselectivity.

  DOI：

  10.1021/jo500441a