2-(2-Methylsulfanyl-2-phenyl-ethylidene)-[1,3]dithiane | 135042-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-(2-Methylsulfanyl-2-phenyl-ethylidene)-[1,3]dithiane
• 英文别名: 2-(2-Methylsulfanyl-2-phenylethylidene)-1,3-dithiane
• CAS: 135042-85-2
• 化学式: C₁₃H₁₆S₃
• 分子量: 268.468
• InChiKey: FRNCFCFPIZAWKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基碘化镁 、 2-Methylsulfanyl-2-((E)-styryl)-[1,3]dithiane 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 乙醚 、 苯 为溶剂， 反应 0.17h， 以23%的产率得到2-(2-Methylsulfanyl-2-phenyl-ethylidene)-[1,3]dithiane
  参考文献：
  名称：

  Transition metal promoted reactions. 38. NiCl2(dppe)-catalyzed geminal dialkylation of dithioacetals and trimethylation of ortho thioesters

  摘要：

  NiCl2(dppe)-catalyzed cross-coupling of cinnamaldehyde dithioacetals gave the corresponding geminal dimethylation products in excellent yields. Allylic ortho thioesters afforded regioselectively the corresponding trimethylation products. The reaction may occur via an 18-electron pi-allyl intermediate, which undergoes facile reductive elimination to afford the geminal dimethylation product. Benzylic dithioacetals having an ortho amino group gave 2-isopropylanilines exclusively. The reaction of benzylic dithioacetals with EtMgBr under the same conditions yielded geminal diethylation products.

  DOI：

  10.1021/jo00018a016

文献信息

• Transition metal promoted reactions. 38. NiCl2(dppe)-catalyzed geminal dialkylation of dithioacetals and trimethylation of ortho thioesters
  作者：Yih Ling Tzeng、Ping Fan Yang、Nai Wen Mei、Tien Min Yuan、Chun Chi Yu、Tien Yau Luh

  DOI：10.1021/jo00018a016

  日期：1991.8

  NiCl2(dppe)-catalyzed cross-coupling of cinnamaldehyde dithioacetals gave the corresponding geminal dimethylation products in excellent yields. Allylic ortho thioesters afforded regioselectively the corresponding trimethylation products. The reaction may occur via an 18-electron pi-allyl intermediate, which undergoes facile reductive elimination to afford the geminal dimethylation product. Benzylic dithioacetals having an ortho amino group gave 2-isopropylanilines exclusively. The reaction of benzylic dithioacetals with EtMgBr under the same conditions yielded geminal diethylation products.