4-chlorophenylthiomethylenecyclohexane | 1332526-20-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-chlorophenylthiomethylenecyclohexane
• 英文别名: 1-Chloro-4-(cyclohexylidenemethylsulfanyl)benzene
• CAS: 1332526-20-1
• 化学式: C₁₃H₁₅ClS
• 分子量: 238.781
• InChiKey: RMTIXQPFYSQENN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 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

• 作为产物：
  描述：

  (iodomethylene)cyclohexane 、 4-氯苯硫酚 在 copper(I) oxide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以85%的产率得到4-chlorophenylthiomethylenecyclohexane
  参考文献：
  名称：

  Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides

  摘要：

  The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couple with aryl iodides in the presence of only 0.5 mol % Cu2O without the need for an ancillary ligand. In the presence of 5 mol % of Cu2O and 10 mol % 1,10-phenanthroline as the ligand, the more challenging alkyl vinyl bromides can also be coupled with thiols, giving the vinyl sulfides in good to excellent yields.

  DOI：

  10.1021/ol2020863

文献信息

• Synthesis of Alkenyl Sulfides Through the Iron-Catalyzed Cross-Coupling Reaction of Vinyl Halides with Thiols
  作者：Yun-Yung Lin、Yu-Jen Wang、Che-Hung Lin、Jun-Hao Cheng、Chin-Fa Lee

  DOI：10.1021/jo3008397

  日期：2012.7.20

  here the iron-catalyzed cross-coupling reaction of alkyl vinyl halides with thiols. While many works are devoted to the coupling of thiols with alkyl vinyl iodides, interestingly, the known S-vinylation of vinyl bromides and chlorides is limited to 1-(2-bromovinyl)benzene and 1-(2-chlorovinyl)benzene. Investigation on the coupling reaction of challenging alkyl vinyl bromides and chlorides with thiols

  我们在这里报告了烷基乙烯基卤化物与硫醇的铁催化交叉偶联反应。尽管许多工作致力于硫醇与烷基乙烯基碘的偶联，但是有趣的是，已知的乙烯基溴和氯化物的S-乙烯基化仅限于1-（2-溴乙烯基）苯和1-（2-氯乙烯基）苯。难于研究具有挑战性的烷基乙烯基溴化物和氯化物与硫醇的偶联反应。由于1-（2-溴乙烯基）苯和1-（2-氯乙烯基）苯与硫醇的偶联可以在不存在任何催化剂的情况下进行，因此在此我们集中于巯基与烷基乙烯基卤化物的偶联。该体系通常对烷基乙烯基碘和溴化物具有反应性，以提供高收率的产物。1-（氯亚甲基）-4-叔丁基丁基环己烷也与硫醇偶联，以中等收率得到目标化合物。
• Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides
  作者：Hsin-Lun Kao、Chin-Fa Lee

  DOI：10.1021/ol2020863

  日期：2011.10.7

  The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couple with aryl iodides in the presence of only 0.5 mol % Cu2O without the need for an ancillary ligand. In the presence of 5 mol % of Cu2O and 10 mol % 1,10-phenanthroline as the ligand, the more challenging alkyl vinyl bromides can also be coupled with thiols, giving the vinyl sulfides in good to excellent yields.