sec-Butyl hexyl sulfide | 138149-07-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: sec-Butyl hexyl sulfide
• 英文别名: 1-[(Butan-2-yl)sulfanyl]hexane；1-butan-2-ylsulfanylhexane
• CAS: 138149-07-2
• 化学式: C₁₀H₂₂S
• 分子量: 174.351
• InChiKey: BRZCWUSPVLTGJY-UHFFFAOYSA-N

物化性质

• 沸点：
  220.8±8.0 °C(Predicted)
• 密度：
  0.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-丁硫醇 、 溴己烷 以81%的产率得到sec-Butyl hexyl sulfide
  参考文献：
  名称：

  The Regioselective Reaction of Atomic Hydrogen with Unsymmetric Disulfides and Sulfides

  摘要：

  Unsymmetric disulfides undergo solution phase reduction with atomic hydrogen regioselectively by displacement at the least hindered sulfur atom. The cleavage of the sulfur-sulfur bond forms mixtures of two thiol and two thiyl radicals. At the temperature at which the reactions are carried out, the thiyl radicals form symmetric disulfides by thiyl-thiyl radical coupling and not by thiyl radical displacement on the starting material. The reaction of atomic hydrogen with an unsymmetric sulfide is a cleavage that favors the formation of the most stable radical. The reaction of phenyl cyclohexyl sulfide produces benzene, cyclohexane, cyclohexyl thiol, and thiophenol. Benzene and cyclohexyl thiol produced from the cleavage of the phenyl-sulfur bond are proposed to arise from the ct-scission of an intermediate formed by ipso-addition of atomic hydrogen to the benzene ring.

  DOI：

  10.1021/jo00119a027

文献信息

• Reaction mechanisms of thioetherification for mercaptans and olefins over sulfided Mo-Ni/Al 2 O 3 catalysts
  作者：Zhibing Shen、Ming Ke、Pei Yu、Haiqiang Hu、Zhaozheng Song、Qingzhe Jiang

  DOI：10.1016/j.molcata.2014.09.034

  日期：2015.1

  The thioetherification reaction of 1-butanethiol and 1-hexene dissolved in n-hexane was investigated over sulfided Mo-Ni/Al2O3 catalysts. The experimental results showed the catalysts have good catalytic performance for thioetherification reaction, but the isomerization and hydrogenation reactions of olefins over the catalysts can inhibit thioetherification reaction. As reaction temperature increases, the isomerization and hydrogenation reactions of olefins increase rapidly, however, the inhibition of thioetherification reaction also increases. The sulfur distribution and molecular structures of sulfur compounds in the products were analyzed by the gas chromatograph with sulfur chemiluminescence detector (GC-SCD) and the gas chromatograph/mass spectra spectrometry (GC/MS). Two possible routes of thioetherification reaction could be observed. At low temperature, the major pathway involves a direct addition of 1-butanethiol to the terminal carbon of double bond of 1-hexene. In this mechanism, the main product is anti-Markovnikov adduct. At a higher temperature, the C-S bond of 1-butanethiol can be subsequently cleaved, and the adsorbed -SH species can be formed on the catalysts. On the same time, abundant 1-hexene can be absorbed on the catalysts, as well. Therefore, the adsorbed SH species can then recombine with adsorbed 1-hexene to form new hexyl-mercaptans, which can continue to produce another kind of thioether (di-hexyl sulfide) with adsorbed 1-hexene. Similar with the first reaction route, the thioether of the anti-Markonikov adduct still dominates in the product. (C) 2014 Elsevier B.V. All rights reserved.
• The Regioselective Reaction of Atomic Hydrogen with Unsymmetric Disulfides and Sulfides
  作者：Dennis D. Tanner、Liying Zhang、Markandu Vigneswaran、Pramod Kandanarachchi

  DOI：10.1021/jo00119a027

  日期：1995.7

  Unsymmetric disulfides undergo solution phase reduction with atomic hydrogen regioselectively by displacement at the least hindered sulfur atom. The cleavage of the sulfur-sulfur bond forms mixtures of two thiol and two thiyl radicals. At the temperature at which the reactions are carried out, the thiyl radicals form symmetric disulfides by thiyl-thiyl radical coupling and not by thiyl radical displacement on the starting material. The reaction of atomic hydrogen with an unsymmetric sulfide is a cleavage that favors the formation of the most stable radical. The reaction of phenyl cyclohexyl sulfide produces benzene, cyclohexane, cyclohexyl thiol, and thiophenol. Benzene and cyclohexyl thiol produced from the cleavage of the phenyl-sulfur bond are proposed to arise from the ct-scission of an intermediate formed by ipso-addition of atomic hydrogen to the benzene ring.