1-[2-Chloro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydro-1H-indol-4-one | 426823-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-[2-Chloro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydro-1H-indol-4-one
• 英文别名: 1-[2-chloro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-3-(2,2,2-trichloroethyl)-5,7-dihydroindol-4-one
• CAS: 426823-96-3
• 化学式: C₂₀H₁₈Cl₄F₃NO
• mdl: MFCD02933728
• 分子量: 487.176
• InChiKey: IBBVOZRYPSEHKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-Chloro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydro-1H-indol-4-one 在 硫酸 作用下， 反应 4.0h， 以86%的产率得到2-{1-[2-Chloro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-YL}acetic acid
  参考文献：
  名称：

  摘要：

  A new method for the synthesis of N-substituted 2-(4-oxo-4,5,6,7-tetrahydroindol-3-yl)acetic acids was developed, Alkylation of cyclic 1,3-diketones with 3,5,5,5-tetrachloropentan-2-one affords 1,4-diketones, which undergo cyclization with different primary amines into N-substituted 3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydroindol-4-ones. Acid hydrolysis of the latter gives the corresponding indol-3-ylacetic acids. The structures of the compounds obtained were confirmed by H-1 and C-13 NMR data.

  DOI：

  10.1023/a:1014067125564
• 作为产物：
  描述：

  3,5,5,5-tetrachloro-2-pentanone 在 氢氧化钾 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 44.0h， 生成 1-[2-Chloro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydro-1H-indol-4-one
  参考文献：
  名称：

  摘要：

  A new method for the synthesis of N-substituted 2-(4-oxo-4,5,6,7-tetrahydroindol-3-yl)acetic acids was developed, Alkylation of cyclic 1,3-diketones with 3,5,5,5-tetrachloropentan-2-one affords 1,4-diketones, which undergo cyclization with different primary amines into N-substituted 3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydroindol-4-ones. Acid hydrolysis of the latter gives the corresponding indol-3-ylacetic acids. The structures of the compounds obtained were confirmed by H-1 and C-13 NMR data.

  DOI：

  10.1023/a:1014067125564

文献信息

• ——
  作者：A. A. Dudinov、D. V. Kozhinov、M. M. Krayushkin

  DOI：10.1023/a:1014067125564

  日期：——

  A new method for the synthesis of N-substituted 2-(4-oxo-4,5,6,7-tetrahydroindol-3-yl)acetic acids was developed, Alkylation of cyclic 1,3-diketones with 3,5,5,5-tetrachloropentan-2-one affords 1,4-diketones, which undergo cyclization with different primary amines into N-substituted 3-(2,2,2-trichloroethyl)-4,5,6,7-tetrahydroindol-4-ones. Acid hydrolysis of the latter gives the corresponding indol-3-ylacetic acids. The structures of the compounds obtained were confirmed by H-1 and C-13 NMR data.