(3S)-(E)-1-(phenylsulfonyl)hex-1-en-3-ol | 140462-48-2

• 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: (3S)-(E)-1-(phenylsulfonyl)hex-1-en-3-ol
• 英文别名: (E,3S)-1-(benzenesulfonyl)hex-1-en-3-ol
• CAS: 140462-48-2
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: NGOYAFMPKPRKHX-USKTWTLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-(E)-1-(phenylsulfonyl)hex-1-en-3-ol 在 lithium t-butyl peroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到(S)-1-(3-Benzenesulfonyl-oxiranyl)-butan-1-ol
  参考文献：
  名称：

  Control of diastereofacial selectivity in the nucleophilic epoxidation of γ-oxygenated-α,β-unsaturated sulphones

  摘要：

  Epoxidation of gamma-oxygenated-alpha,beta-unsaturated sulphones 4-8 with lithium t-butyl hydroperoxide proceeds with moderate to high diastereoselectivity to give 2-phenylsulphonyl oxiranes 9-13. The sense of diastereoselectivity is dependent on the steric bulk of the alkyl substituent at the gamma-centre.

  DOI：

  10.1016/s0040-4039(00)92395-5
• 作为产物：
  描述：

  (2R,3S)-2-<(phenylsulfonyl)methyl>-3-propyloxirane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(3S)-(E)-1-(phenylsulfonyl)hex-1-en-3-ol
  参考文献：
  名称：

  Homochiral 2,3-epoxy sulfides as precursors to -γ-hydroxy-α,β-unsaturated sulfoxides and sulfones.

  摘要：

  The synthesis of E-gamma-hydroxy-alpha,beta-unsaturated sulfoxides and sulfones from the corresponding homochiral 2,3-epoxy sulfides is described with excellent control of double bond geometry and stereochemistry at both the sulfoxide and secondary alcohol chiral centres.

  DOI：

  10.1016/s0957-4166(00)86205-9

文献信息

• Homochiral 2,3-epoxy sulfides—powerful new synthetic building blocks providing stereoselective access to 2,3-epoxy sulfoxides, 2,3-dihydroxy sulfoxides and (E)-γ-hydroxy-α,β-unsaturated sulfoxides and sulfones. X-Ray molecular structure of rac-(2R*,3R*)-1-[(S*)-phenylsulfinyl] hexane-2,3-diol
  作者：Andrew D. Westwell、Mark Thornton-Pett、Christopher M. Rayner

  DOI：10.1039/p19950000847

  日期：——

  The stereoselective transformation of homochiral 2,3-epoxy sulfoxides into 2,3-epoxy sulfoxides is described. These intermediates undergo elimination under basic reaction conditions to give (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides, and under Lewis acidic conditions form novel cyclic sulfoxonium salts which on hydrolysis give 2,3-dihydroxy sulfoxides with excellent stereochemical control. 2,3-Dihydroxy sulfoxides can also be converted into (E)-gamma-hydroxy-alpha,beta-unsaturated sulfoxides by elimination via a cyclic sulfite. The synthesis of (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones by base-catalysed elimination of a 2,3-epoxy sulfone is also described.
• A new method for the dehydration of β-hydroxy sulfones: synthesis of (E,S)-γ-hydroxy-α,β-unsaturated sulfones and (S)-ε-hydroxy-(E,E)-α,γ-dienyl sulfones
  作者：Suk-Ku Kang、Young-Won Park、Sung-Gyu Kim、Jae-Hoon Jeon

  DOI：10.1039/p19920000405

  日期：——

  Optically active (E,S)-gamma-hydroxy-alpha,beta-unsaturated sulfones and (S)-epsilon-hydroxy-(E,E)-alpha,gamma-dienyl sulfones have been prepared in a one-pot dehydration procedure from beta,gamma-dihydroxy sulfones and delta,epsilon-dihydroxy allyl sulfones, respectively, via an elimination reaction of the corresponding cyclic sulfites or carbonates formed in situ by treatment with thionyl chloride or carbonyldiimidazole.