2,2,4-trimethyl-1,4-dihydro-2H-cyclopenta[b]indol-3-one | 848623-54-1

• 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: 2,2,4-trimethyl-1,4-dihydro-2H-cyclopenta[b]indol-3-one
• 英文别名: 2,2,4-trimethyl-1H-cyclopenta[b]indol-3-one
• CAS: 848623-54-1
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: QYKBBYHVYGPLGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,4-trimethyl-1,4-dihydro-2H-cyclopenta[b]indol-3-one 在 碘 对甲苯磺酸 、 magnesium 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.33h， 生成 1,4,4-trimethyl-3-phenyl-4,5-dihydro-1H,3H-benzo[b]azocine-2,6-dione
  参考文献：
  名称：

  Incorporation of an indole-containing diarylbutylamine pharmacophore into furo[2,3-a]carbazole ring systems

  摘要：

  Due to concurrent oxidation of the indole moiety in the starting carbazole alkenol, an epoxidation route aiming at incorporation of a conformationally constrained diarylbutylamine failed to give the desired furo[2,3-a]carbazole ring system. Instead, an indole epoxide intermediate was generated, which underwent rearrangement involving participation of a vicinal OH group. The required furo[2,3-a]2 carbazole could, however, be accessed via a Hg2+-induced cyclisation of a carbazole alkynol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.049
• 作为产物：
  描述：

  4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one 、 碘甲烷 在 potassium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以71%的产率得到2,2,4-trimethyl-1,4-dihydro-2H-cyclopenta[b]indol-3-one
  参考文献：
  名称：

  Incorporation of an indole-containing diarylbutylamine pharmacophore into furo[2,3-a]carbazole ring systems

  摘要：

  Due to concurrent oxidation of the indole moiety in the starting carbazole alkenol, an epoxidation route aiming at incorporation of a conformationally constrained diarylbutylamine failed to give the desired furo[2,3-a]carbazole ring system. Instead, an indole epoxide intermediate was generated, which underwent rearrangement involving participation of a vicinal OH group. The required furo[2,3-a]2 carbazole could, however, be accessed via a Hg2+-induced cyclisation of a carbazole alkynol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.049

文献信息

• Incorporation of an indole-containing diarylbutylamine pharmacophore into furo[2,3-a]carbazole ring systems
  作者：Faye Maertens、Suzanne Toppet、Georges J. Hoornaert、Frans Compernolle

  DOI：10.1016/j.tet.2004.12.049

  日期：2005.2

  Due to concurrent oxidation of the indole moiety in the starting carbazole alkenol, an epoxidation route aiming at incorporation of a conformationally constrained diarylbutylamine failed to give the desired furo[2,3-a]carbazole ring system. Instead, an indole epoxide intermediate was generated, which underwent rearrangement involving participation of a vicinal OH group. The required furo[2,3-a]2 carbazole could, however, be accessed via a Hg2+-induced cyclisation of a carbazole alkynol. (C) 2004 Elsevier Ltd. All rights reserved.