(+/-)-(E)-1-(phenylsulfonyl)-1-penten-3-ol | 137653-98-6

• 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: (+/-)-(E)-1-(phenylsulfonyl)-1-penten-3-ol
• 英文别名: (E)-1-(benzenesulfonyl)pent-1-en-3-ol
• CAS: 137653-98-6
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: ZHGPNNIKXFVMLL-CMDGGOBGSA-N

物化性质

• 沸点：
  427.5±37.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(E)-1-(phenylsulfonyl)-1-penten-3-ol 在 pyridinium chlorochromate on silica gel 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 98.0h， 生成 (Z)-1-(benzenesulfonyl)pent-1-en-3-one
  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
• 作为产物：
  描述：

  正丁醛 、 (R)-(phenylsulfonyl)(p-tolylsulfinyl)methane 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(+/-)-(E)-1-(phenylsulfonyl)-1-penten-3-ol
  参考文献：
  名称：

  Dominguez, E.; Carretero, J. C., Anales de Quimica, 1994, vol. 90, # 7-8, p. 397 - 402

  摘要：

  DOI：

文献信息

• An efficient preparation of optically active (E)-γ-hydroxy-α,β-unsaturated phenyl sulfones using lipase-mediated acylations
  作者：Esteban Domínguez、Juan Carlos Carretero、Alfonso Fernández-Mayoralas、Santiago Conde

  DOI：10.1016/s0040-4039(00)93455-5

  日期：1991.9

  (E)-gamma-Hydroxy-alpha,beta-unsaturated phenyl sulfones have been efficiently resolved via irreversible enzymatic acylation with lipase PS (pseudomonas cepacia) and vinyl acetate. This process has been applied to the synthesis of the aggregation pheromone (-)-(3S,4S)-4-methyl-3-heptanol.

  (E)-γ-羟基α,β-不饱和苯砜在双歧杆菌PS（双歧杆菌Cepacia）酶催作用以及乙酰醋酸二注射液的配合下，通过不可逆的酶促甲基化过程得到脱炔酮双键。此方法已被用于合成的聚合外ustedache，（-）-（3S,4S）—4-甲基-3-Heptanol。
• Synthesis and conjugate additions to (E)-γ-alkoxy-α-substituted-α,β-unsaturated sulfones
  作者：Carmen Alcaraz、Juan C. Carretero、Esteban Domínguez

  DOI：10.1016/s0040-4039(00)79674-2

  日期：1991.3

  (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones have been readily functionalized at alpha-position via protection of hydroxyl group, metalation with n-BuLi and subsequent reaction with electrophiles. The conjugate addition of organolithiums to (E)-gamma-methoxymethoxy-alpha-trimethylsilyl-alpha, beta-unsaturated phenyl sulfones in Et2O is highly syn-stereoselective.

  (E)-γ-羟基-α,β-未饱和砜经过羟基的保护后，可以在α位置容易地进行功能化反应。添加三甲基--硅基α,β-未饱和苯砜的有机锂试剂在乙醚中的共轭加成具有高度的合成同素异构选择性。