2-Methylsulfanyl-2-((E)-styryl)-[1,3]dithiane | 130573-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Methylsulfanyl-2-((E)-styryl)-[1,3]dithiane
• 英文别名: 2-(Methylthio)-2-styryl-1,3-dithiane；2-methylsulfanyl-2-[(E)-2-phenylethenyl]-1,3-dithiane
• CAS: 130573-25-0
• 化学式: C₁₃H₁₆S₃
• 分子量: 268.468
• InChiKey: PFJRWXJVTHMZNJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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

• 作为反应物：
  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 16.0h， 以74%的产率得到2-methyl-4-phenyl-2-pentene
  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

• Ni, Zhi-Jie; Yang, Pin-Fan; Ng, Dennis K. P., Journal of the American Chemical Society, 1990, vol. 112, # 25, p. 9356 - 9364
  作者：Ni, Zhi-Jie、Yang, Pin-Fan、Ng, Dennis K. P.、Tzeng, Yih-Ling、Luh, Tien-Yau

  DOI：——

  日期：——
• NI, ZHI-JIE;YANG, PIN-FAN;NG, DENNIS K. P.;TZENG, YIH-LING;LUH, TIEN-YAU, J. AMER. CHEM. SOC., 112,(1990) N5, C. 9356-9364
  作者：NI, ZHI-JIE、YANG, PIN-FAN、NG, DENNIS K. P.、TZENG, YIH-LING、LUH, TIEN-YAU

  DOI：——

  日期：——
• 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.