1-azido-3-((4-chlorophenyl)thio)propan-2-ol | 613261-30-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-azido-3-((4-chlorophenyl)thio)propan-2-ol
• 英文别名: 1-azido-3-(4-chlorophenylthio)-2-propanol；1-Azido-3-(4-chlorophenyl)sulfanylpropan-2-ol
• CAS: 613261-30-6
• 化学式: C₉H₁₀ClN₃OS
• 分子量: 243.717
• InChiKey: CMQJQIDLIPCOBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸异丙烯酯 、 1-azido-3-((4-chlorophenyl)thio)propan-2-ol 在 Chirazyme L-2 (c-f lyo) Candida antarctica lipase 作用下， 以 甲苯 为溶剂， 反应 52.0h， 生成 (R)-1-azido-3-((4-chlorophenyl)thio)propan-2-ol 、 (S)-1-azido-3-((4-chlorophenyl)thio)propan-2-ol 、 (S)-(-)-1-azido-3-((4-chlorophenyl)thio)propan-2-yl acetate 、 (R)-(-)-1-azido-3-((4-chlorophenyl)thio)propan-2-yl acetate
  参考文献：
  名称：

  Lipase-catalyzed separation of the enantiomers of 1-substituted-3-arylthio-2-propanols

  摘要：

  Optically active (R)- and (S)-1-substituted-3-(arylthio)propan-2-ols have been prepared in the reaction of the appropriate 2-(arylthiomethyl)oxiranes with chloride and azide anions followed by a lipase-catalyzed transesterification. The effects of the enzyme preparation as well as of the reaction conditions have been compared in terms of the enantiomeric excess of the obtained acetate and unreacted alcohol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.040
• 作为产物：
  描述：

  (4-chloro-phenylsulfanylmethyl)-oxirane 在 sodium azide 、 samarium(III) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到1-azido-3-((4-chlorophenyl)thio)propan-2-ol
  参考文献：
  名称：

  High Yield Regioselective Ring Opening of Epoxides Using Samarium Chloride Hexahydrate

  摘要：

  Epoxides were converted to the corresponding beta-azidohydrins and beta-iodohydrins using SmCl3.6H(2)O/NaN3 in DMF and SMCl3.6H(2)O/ NaI in acetonitrile respectively. The reactions were highly regioselective, efficient, and gave excellent yields under mild and neutral conditions.

  DOI：

  10.1081/scc-120018790

文献信息

• High Yield Regioselective Ring Opening of Epoxides Using Samarium Chloride Hexahydrate
  作者：Kankan Bhaumik、Umesh W. Mali、K. G. Akamanchi

  DOI：10.1081/scc-120018790

  日期：2003.1.5

  Epoxides were converted to the corresponding beta-azidohydrins and beta-iodohydrins using SmCl3.6H(2)O/NaN3 in DMF and SMCl3.6H(2)O/ NaI in acetonitrile respectively. The reactions were highly regioselective, efficient, and gave excellent yields under mild and neutral conditions.
• Lipase-catalyzed separation of the enantiomers of 1-substituted-3-arylthio-2-propanols
  作者：Monika Wielechowska、Jan Plenkiewicz

  DOI：10.1016/j.tetasy.2005.01.040

  日期：2005.3

  Optically active (R)- and (S)-1-substituted-3-(arylthio)propan-2-ols have been prepared in the reaction of the appropriate 2-(arylthiomethyl)oxiranes with chloride and azide anions followed by a lipase-catalyzed transesterification. The effects of the enzyme preparation as well as of the reaction conditions have been compared in terms of the enantiomeric excess of the obtained acetate and unreacted alcohol. (C) 2005 Elsevier Ltd. All rights reserved.