(S)-1-(苯基磺酰基)-3-戊醇 | 131701-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-(苯基磺酰基)-3-戊醇
• 英文名称: (S)-1-(phenylsulfonyl)-3-pentanol
• 英文别名: (3S)-1-(benzenesulfonyl)pentan-3-ol
• CAS: 131701-89-8
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: RFTIMXHALPDPSO-JTQLQIEISA-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)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-(phenylsulfonyl)(p-tolylsulfinyl)methane 在 palladium on activated charcoal 哌啶 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 27.5h， 生成 (S)-1-(苯基磺酰基)-3-戊醇
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of .gamma.-hydroxy phenyl sulfones

  摘要：

  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.

  DOI：

  10.1021/jo00040a028

文献信息

• 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.
• GOPALAN, ARAVAMUDAN S.;JACOBS, HOLLIE K., TETRAHEDRON LETT., 31,(1990) N9, C. 5575-5578
  作者：GOPALAN, ARAVAMUDAN S.、JACOBS, HOLLIE K.

  DOI：——

  日期：——
• 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.