N-[(2-bromophenyl)methyl]-2-chloro-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide | 205446-82-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-[(2-bromophenyl)methyl]-2-chloro-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide
• CAS: 205446-82-8
• 化学式: C₂₂H₂₃BrClNOS₂
• 分子量: 496.92
• InChiKey: YKNFWPVCAHIZDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2-bromophenyl)methyl]-2-chloro-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide 在 盐酸 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-[(2-bromophenyl)methyl]-3-methylsulfanyl-7a-phenylsulfanyl-4,5,6,7-tetrahydroindol-2-one
  参考文献：
  名称：

  New Entry to 1,4,5,6-Tetrahydro-2H-indol-2-ones Using a Cationic 5-endo-trigonal Cyclization onto Enamides

  摘要：

  A new method for the synthesis of 1,4,5,6-tetrahydro-2H-indol-2-ones by means of 5-endo-trigonal cyclization of alpha-thiocarbocations generated from sulfoxide (12) and alpha-chlorosulfide (17) is described. The sulfoxide (12), upon heating with TsOH, gave 14, which eliminated benzenethiol to give tetrahydroindolone (15). By contrast, the chlorosulfide (17), upon treatment with TiCL4 gave the desulfurized tetrahydroindolone (18). The mechanism for the formation of 18 is also discussed.

  DOI：

  10.3987/com-97-s8
• 作为产物：
  描述：

  2-phenylthiocyclohexanone 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 甲苯 为溶剂， 生成 N-[(2-bromophenyl)methyl]-2-chloro-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide
  参考文献：
  名称：

  New Entry to 1,4,5,6-Tetrahydro-2H-indol-2-ones Using a Cationic 5-endo-trigonal Cyclization onto Enamides

  摘要：

  A new method for the synthesis of 1,4,5,6-tetrahydro-2H-indol-2-ones by means of 5-endo-trigonal cyclization of alpha-thiocarbocations generated from sulfoxide (12) and alpha-chlorosulfide (17) is described. The sulfoxide (12), upon heating with TsOH, gave 14, which eliminated benzenethiol to give tetrahydroindolone (15). By contrast, the chlorosulfide (17), upon treatment with TiCL4 gave the desulfurized tetrahydroindolone (18). The mechanism for the formation of 18 is also discussed.

  DOI：

  10.3987/com-97-s8

文献信息

• New Entry to 1,4,5,6-Tetrahydro-2H-indol-2-ones Using a Cationic 5-endo-trigonal Cyclization onto Enamides
  作者：Hiroyuki Ishibashi、Masahiro Higuchi、Hiromi Masuko、Kazuya Kodama、Masazumi Ikeda

  DOI：10.3987/com-97-s8

  日期：——

  A new method for the synthesis of 1,4,5,6-tetrahydro-2H-indol-2-ones by means of 5-endo-trigonal cyclization of alpha-thiocarbocations generated from sulfoxide (12) and alpha-chlorosulfide (17) is described. The sulfoxide (12), upon heating with TsOH, gave 14, which eliminated benzenethiol to give tetrahydroindolone (15). By contrast, the chlorosulfide (17), upon treatment with TiCL4 gave the desulfurized tetrahydroindolone (18). The mechanism for the formation of 18 is also discussed.