methyl 9-methyl-1-oxo-2-(2-propynyl)-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate | 848623-60-9

• 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: methyl 9-methyl-1-oxo-2-(2-propynyl)-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate
• 英文别名: Methyl 9-methyl-1-oxo-2-prop-2-ynyl-3,4-dihydrocarbazole-2-carboxylate
• CAS: 848623-60-9
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: KSJSWQVKDKNJMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 9-methyl-1-oxo-2-(2-propynyl)-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate 在 碘 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 对甲苯磺酸 、 magnesium 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 74.0h， 生成 methyl (3aRS,10bRS)-2-[(dimethylamino)methyl]-2-hydroxy-10-methyl-10b-phenyl-2,3,4,5,10,10b-hexahydro-3aH-furo[2,3-a]carbazole-3a-carboxylate
  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：

  3-溴丙炔 、 methyl 9-methyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate 在 sodium hydride 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到methyl 9-methyl-1-oxo-2-(2-propynyl)-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate
  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