(2R*,3S*)-1-benzyl-3-hydroxy-2-phenylazetidine | 141811-85-0

• 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: (2R*,3S*)-1-benzyl-3-hydroxy-2-phenylazetidine
• 英文别名: (2S,3R)-1-benzyl-2-phenylazetidin-3-ol
• CAS: 141811-85-0
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: BCILNHQTMHYVDO-CVEARBPZSA-N

物化性质

• 沸点：
  369.6±42.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  (+/-)-threo-2-[bromo(phenyl)methyl]-oxirane 、 苄胺 以 甲醇 为溶剂， 反应 20.0h， 以92%的产率得到(2R*,3S*)-1-benzyl-3-hydroxy-2-phenylazetidine
  参考文献：
  名称：

  Synthesis of 1-Alkyl-3-hydroxy-2-phenylazetidines

  摘要：

  Several (R*, S*)-1-alkyl-3-hydroxy-2-phenylazetidines (1) were synthesized by the reaction of (R*, R*)-2-(1-bromobenzyl)oxirane (2a) with aliphatic primary amines in good yields. By the reaction of (R*, S*)-2-(1-bromobenzyl)oxirane (2b), only (R*, R*)-2-aminomethyl-3-phenyloxirane (3) was obtained. Also, the reaction of (R*, R*)-2-(1-bromobenzyl)-2-methyloxirane (2c) gave a mixture of (R*, S*)-3-hydroxy-3-methyl-2-phenylazetidine (4) as the major product and (R*, S*)-2-aminomethyl-2-methyl-3-phenyloxirane (5) as the minor product.

  DOI：

  10.3987/com-91-s74

文献信息

• Stereoselective synthesis of 3-hydroxyazetidines via regioselective halogenation of 2,3-epoxyamines by using magnesium bromide
  作者：Michinori Karikomi、Kouji Arai、Takashi Toda

  DOI：10.1016/s0040-4039(97)01360-9

  日期：1997.8

  A novel stereoselective synthesis of 3-hydroxyazetidines starting from 2,3-epoxyamines is described. Regioselectivity of the intramolecular cyclization of 2,3-epoxyamines is controlled by the use of magnesium bromide. The cyclization proceeds with retention of the stereochemistry, caused by double inversion of two sequential SN2 reactions of the epoxyamines.

  描述了从2，3-环氧胺开始的3-羟基氮杂环丁烷的新颖的立体选择性合成。通过使用溴化镁来控制2，3-环氧胺的分子内环化的区域选择性。由于环氧胺的两个连续S N 2反应的两次反转，环化过程将保留立体化学。