2-(thiophenyl)octan-1-ol | 476305-03-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(thiophenyl)octan-1-ol
• 英文别名: 2-Phenylsulfanyloctan-1-ol；2-phenylsulfanyloctan-1-ol
• CAS: 476305-03-0
• 化学式: C₁₄H₂₂OS
• 分子量: 238.394
• InChiKey: PWKCGDIELBQQKF-UHFFFAOYSA-N

物化性质

• 沸点：
  353.9±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(thiophenyl)octan-1-ol 在 二甲基亚砜 、 二异丙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 2-(phenylthio)octanal
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c
• 作为产物：
  描述：

  辛酸乙酯 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.17h， 生成 2-(thiophenyl)octan-1-ol
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c

文献信息

• Thiolysis of Alkyl- and Aryl-1,2-epoxides in Water Catalyzed by InCl3
  作者：Francesco Fringuelli、Ferdinando Pizzo、Simone Tortoioli、Luigi Vaccaro

  DOI：10.1002/1615-4169(200206)344:3/4<379::aid-adsc379>3.0.co;2-4

  日期：2002.6

  The pH dependence of thiolysis of 1,2-epoxides with thiophenol in water and the influence of a Lewis acid catalyst is investigated. InCl3 showed a very high efficiency in catalyzing this process at pH 4.0. The regloselectivity of the nucleophilic attack is markedly influenced going from pH 9.0 to pH 4.0. A one-pot procedure running solely in water to prepare trans-2-(phenylsulphinyl)cyclohexan-1-ol is reported starting from epoxycyclohexane, via thiolysis reaction and oxidation with t-butyl hydroperoxide.
• Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation
  作者：Veejendra K. Yadav、K. Ganesh Babu、Masood Parvez

  DOI：10.1021/jo034608c

  日期：2004.5.1

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.