1-[(2-Bromophenyl)methyl]-3-methylsulfanyl-3a-phenylsulfanyl-3,4,5,6-tetrahydroindol-2-one | 205446-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[(2-Bromophenyl)methyl]-3-methylsulfanyl-3a-phenylsulfanyl-3,4,5,6-tetrahydroindol-2-one
• CAS: 205446-80-6
• 化学式: C₂₂H₂₂BrNOS₂
• 分子量: 460.459
• InChiKey: CEWTXZAJOMOQKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• 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：

  1-[(2-Bromophenyl)methyl]-3-methylsulfanyl-3a-phenylsulfanyl-3,4,5,6-tetrahydroindol-2-one 在 盐酸 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到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：

  N-[(2-bromophenyl)methyl]-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide 在 N-氯代丁二酰亚胺 、 四氯化钛 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-[(2-Bromophenyl)methyl]-3-methylsulfanyl-3a-phenylsulfanyl-3,4,5,6-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