(R)-1-(phenylsulfonyl)-3-pentanol | 148153-94-0

• 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: (R)-1-(phenylsulfonyl)-3-pentanol
• 英文别名: (3R)-1-(benzenesulfonyl)pentan-3-ol
• CAS: 148153-94-0
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: RFTIMXHALPDPSO-SNVBAGLBSA-N

物化性质

• 沸点：
  416.5±37.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (R)-1-(phenylthio)-3-pentanol 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以98%的产率得到(R)-1-(phenylsulfonyl)-3-pentanol
  参考文献：
  名称：

  以粉状毕赤酵母催化反前体规则还原为关键步骤制备含硫光学活性仲醇

  摘要：

  Pichia farinosa IAM 4682 介导的含硫酮还原得到具有 (R)-绝对构型的仲醇。例如，4-(苯硫基)-2-丁酮和4-(苯磺酰基)-2-丁酮以90%的产率提供(R)-4-(苯硫基)-2-丁醇(91%ee)和(R)- 4-(苯磺酰基)-2-丁醇(97%ee)分别为94%产率。在产品的ee不令人满意的情况下，任何污染的(S)-对映体被玫瑰色红球菌IFO 15564选择性氧化，留下纯的(R)-对映体。进一步检查了粉状毕赤酵母介导的还原和玫瑰色红球菌介导的氧化的底物特异性。

  DOI：

  10.1246/bcsj.70.483

文献信息

• Lipase-catalyzed kinetic resolution of .gamma.-hydroxy phenyl sulfones
  作者：Juan C. Carretero、Esteban Dominguez

  DOI：10.1021/jo00040a028

  日期：1992.7

  Lipase PS (from Pseudomonas cepacia) catalyzed the enantioselective transesterification of racemic gamma-hydroxy-alpha,beta-unsaturated phenyl sulfones 1 and their alpha,beta-saturated derivatives 3 with vinyl acetate in an organic solvent (usually (i)Pr2O). Remarkably, in substrates 1 with (E)-stereochemistry, the enantioselectivity of the process was little influenced by the nature of the R chain. Hence, very high enantiomeric ratios (E greater-than-or-equal-to 45) were observed in substrates 1 bearing short (R = Me or Et), long (R = n-Cr6H13 or n-C10H21), bulky (R = (i)Pr), or functionalized R chains. The (R)-enantiomer was the fast-reacting enantiomer in all cases. Concerning the reactivity, the rate of the reaction decreased significantly with an increase in size or length of the R chain (reaction time for 50% conversion from 3.5 to 162 h). Less satisfactory enantioselectivities (E = 5-48) were obtained when the saturated substrates 3 were used instead of the corresponding alpha,beta-unsaturated alcohols 1.
• Microbiological reduction of keto-sulfones. Application in a three-step synthesis of (S)-(+)-β-angelica lactone
  作者：Sylvie Robin、François Huet、Annie Fauve、Henri Veschambre

  DOI：10.1016/s0957-4166(00)82344-7

  日期：1993.2

  Microbiological reductions of several keto-sulfones led to the corresponding hydroxy-sulfones in moderate to high enantiomeric excess. A three-step synthesis of (S)-(+)-beta-angelica lactone from ethyl-4-oxo-3-(phenyl-sulfonyl)-pentanoate via the intermediate chiral alcohol is described.