(2R,3S)-1-cyclohexyl-2-phenylazetidin-3-ol | 32908-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (2R,3S)-1-cyclohexyl-2-phenylazetidin-3-ol
• CAS: 32908-29-5；32908-30-8
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: LQEVSUMQEOAPOR-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-溴苯酚 、 (2R,3S)-1-cyclohexyl-2-phenylazetidin-3-ol 反应 16.0h， 以51%的产率得到threo-1-(4-Bromophenoxy)-3-(cyclohexylamino)-1-phenyl-2-propanol
  参考文献：
  名称：

  Ring Opening of Azetidinols by Phenols: Regiochemistry and Stereochemistry

  摘要：

  Ring opening of a series of 1-alkyl- and 1-benzyl-3-azetidinols by 6-bromophenol without added base is reported. Opening of trans-2-methyl- and cis- and trans-2-phenyl-3-azetidinols is highly regioselective, if not regiospecific. The 2-methyl compounds open by cleavage of the N-C4 bond and the 2-phenyl compounds by cleavage of the N-C2 bond in a highly stereoselective, if not stereospecific, manner, which involves inversion of configuration at C2. The results are rationalized in terms of nucleophilic ring opening of the azetidinium ions.

  DOI：

  10.1021/jo00087a038
• 作为产物：
  描述：

  环己胺 、 (+/-)-threo-2-[bromo(phenyl)methyl]-oxirane 以 甲醇 为溶剂， 反应 67.0h， 以79%的产率得到(2R,3S)-1-cyclohexyl-2-phenylazetidin-3-ol
  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