5-Methyl-1-(phenylthio)-1-cyclohexene | 71624-74-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-Methyl-1-(phenylthio)-1-cyclohexene
• 英文别名: 4-Methyl-2-phenylmercapto-cyclohexen；(5-methylcyclohexen-1-yl)sulfanylbenzene
• CAS: 71624-74-3
• 化学式: C₁₃H₁₆S
• 分子量: 204.336
• InChiKey: JHCHBBRTZWYJAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Methyl-1-(phenylthio)-1-cyclohexene 、 溶剂黄146 以74%的产率得到
  参考文献：
  名称：

  YOSHIDA, JUN-ICHI;NAKATANI, SHOGO;ISOE, SACHIHIKO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 22, C. 1468-1470

  摘要：

  DOI：
• 作为产物：
  描述：

  Methanesulfonic acid 4-methyl-2-phenylsulfanyl-cyclohexyl ester 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 5-Methyl-1-(phenylthio)-1-cyclohexene
  参考文献：
  名称：

  在硫酚存在下通过氧合将链烯基硫化物区域特异性转化为α-磺酰化羰基化合物

  摘要：

  在硫酚的存在下，通过氧化实现烯基硫的区域特异性转化为α-磺苯基化的羰基化合物。发现电解对于引发反应是非常有效的。

  DOI：

  10.1039/c39880001468

文献信息

• Regiospecific conversion of alkenyl sulphides to α-sulphenylated carbonyl compounds by oxygenation in the presence of thiophenol
  作者：Jun-ichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1039/c39880001468

  日期：——

  Regiospecific conversion of alkenyl sulphides to α-sulphenylated carbonyl compounds was achieved by oxygenation in the presence of thiophenol; electrolysis was found to be quite effective for initiation of the reaction.

  在硫酚的存在下，通过氧化实现烯基硫的区域特异性转化为α-磺苯基化的羰基化合物。发现电解对于引发反应是非常有效的。
• YOSHIDA, JUN-ICHI;NAKATANI, SHOGO;ISOE, SACHIHIKO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 22, C. 1468-1470
  作者：YOSHIDA, JUN-ICHI、NAKATANI, SHOGO、ISOE, SACHIHIKO

  DOI：——

  日期：——
• Electroinitiated oxygenation of alkenyl sulfides and alkynes in the presence of thiophenol
  作者：Junichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1021/jo00070a021

  日期：1993.8

  Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding alpha-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity. An electroinitiated radical chain mechanism has been proposed. The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction. The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group. The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding alpha-(phenylthio) thiol esters. It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave alpha-(phenylthio) carbonyl compounds. A mechanism involving the initial formation of alkenyl sulfides has been proposed.