(R)-1-phenylthiopropan-2-yl acetate | 136656-78-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-1-phenylthiopropan-2-yl acetate
• 英文别名: [(2R)-1-phenylsulfanylpropan-2-yl] acetate
• CAS: 136656-78-5
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: SSHJXUWZAZXLND-SECBINFHSA-N

物化性质

• 沸点：
  299.9±23.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-phenylthiopropan-2-yl acetate 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (R,R_S)-1-phenylsulfinyl-2-propanol
  参考文献：
  名称：

  Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: versatile synthons for enantiopure β-hydroxy sulfoxides

  摘要：

  Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00434-7
• 作为产物：
  描述：

  (苯基硫代)丙酮 在 sodium tetrahydroborate 、 Humicola lanuginosa 作用下， 以 乙醇 为溶剂， 反应 12.5h， 生成 (R)-1-phenylthiopropan-2-yl acetate
  参考文献：
  名称：

  Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: versatile synthons for enantiopure β-hydroxy sulfoxides

  摘要：

  Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00434-7

文献信息

• A facile chemoenzymatic route to enantiomerically pure oxiranes: building blocks for biologically active compounds
  作者：Ulrich Goergens、Manfred P. Schneider

  DOI：10.1039/c39910001064

  日期：——

  The enantiomerically pure building blocks (R)-and (S)-1–4 were prepared both by enantioselective, enzymatic hydrolysis and by acyl transfer, and subsequently converted into the corresponding enantiomerically pure oxiranes (R)- and (S)-7 and 8.

  对映体纯积木（[R ）-和（小号） - 1 - 4通过对映体选择性，酶水解和通过酰基转移制备两者，并随后转化为相应的对映体纯的环氧乙烷（[R ） -和（小号） - 7和8。
• Enzymatic kinetic resolution of organochalcogenides in supercritical CO2
  作者：Rogério A. Gariani、Fernando A.G. Luengo、Luiz A.S. Vale、Reinaldo C. Bazito、João V. Comasseto

  DOI：10.1016/j.tetlet.2011.04.073

  日期：2011.6

  1-(Phenylthio)-, 1-(phenylseleno)- and 1-(phenyltelluro)-propan-2-ol were efficiently resolved by CAL-B in sc-CO2. (C) 2011 Elsevier Ltd. All rights reserved.