(2S,3S,4S)-(1,4-dimethyl-3-phenylazetidin-2-yl)diphenylmethanol

• 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: (2S,3S,4S)-(1,4-dimethyl-3-phenylazetidin-2-yl)diphenylmethanol
• 英文别名: [(2S,3S,4S)-1,4-dimethyl-3-phenylazetidin-2-yl]-diphenylmethanol
• 化学式: C₂₄H₂₅NO
• 分子量: 343.469
• InChiKey: AJOYFMHIFTUZKF-NMNUPHIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2S,3S,4S)-1,4-dimethyl-3-phenyl-azetidine-2-carbonitrile 在 silica gel 作用下， 以 乙醚 、 环己烷 、 Petroleum ether 、 苯 为溶剂， 反应 0.5h， 生成 (2S,3S,4S)-(1,4-dimethyl-3-phenylazetidin-2-yl)diphenylmethanol
  参考文献：
  名称：

  Synthesis of enantiopure 2-acyl azetidines and the application of amino alcohols derived therefrom in enantioselective catalysis

  摘要：

  Enantiopure 2-acyl azetidines were prepared in good yields from 2-cyano azetidines. The ketones produced were then stereo selectively reduced with sodium borohydride (with or without zinc bromide) or transformed into tertiary azetidinic amino alcohols by addition of phenyllithium. The latter compounds were found to be highly efficient catalysts for the enantioselective addition of diethylzinc to aldehydes, giving enantioselectivities up to 98%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00710-3

文献信息

• Synthesis of enantiopure 2-acyl azetidines and the application of amino alcohols derived therefrom in enantioselective catalysis
  作者：François Couty、Damien Prim

  DOI：10.1016/s0957-4166(02)00710-3

  日期：2002.11

  Enantiopure 2-acyl azetidines were prepared in good yields from 2-cyano azetidines. The ketones produced were then stereo selectively reduced with sodium borohydride (with or without zinc bromide) or transformed into tertiary azetidinic amino alcohols by addition of phenyllithium. The latter compounds were found to be highly efficient catalysts for the enantioselective addition of diethylzinc to aldehydes, giving enantioselectivities up to 98%. (C) 2002 Elsevier Science Ltd. All rights reserved.