9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole | 266326-32-3

• 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: 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole
• 英文别名: (5,7-dimethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)-phenylmethanone
• CAS: 266326-32-3
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: ZTJUCRNMXWSQIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole 在 lithium hydroxide 、 溴 、 四氯苯醌 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 苯 为溶剂， 反应 17.0h， 生成 3-bromo-2,4-dimethoxycarbazole
  参考文献：
  名称：

  Synthesis and pharmacology of a hybrid cannabinoid

  摘要：

  A pentacyclic hybrid cannabinoid (4) has been synthesized, which combines structural elements of traditional cannabinoids and cannabmimetic indoles. Cannabinoid 4 contains a 1-pentylindole structure fused to the 2,3-positions of the partially reduced hydroxydibenzopyran system of THC. The successful approach to 4 employed 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole (17) as the starting material. Dehydrogenation to carbazole 18, followed by demethylation and condensation with trans-p-menthadienol gave N-benzoyl hybrid cannabinoid 22, N-alkylation of which afforded target cannabinoid 4. The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of Delta(8)-THC (K-i=19.3+/-3 nM), and shows comparable potency in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00305-3
• 作为产物：
  描述：

  2-氯环己酮 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  Synthesis and pharmacology of a hybrid cannabinoid

  摘要：

  A pentacyclic hybrid cannabinoid (4) has been synthesized, which combines structural elements of traditional cannabinoids and cannabmimetic indoles. Cannabinoid 4 contains a 1-pentylindole structure fused to the 2,3-positions of the partially reduced hydroxydibenzopyran system of THC. The successful approach to 4 employed 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole (17) as the starting material. Dehydrogenation to carbazole 18, followed by demethylation and condensation with trans-p-menthadienol gave N-benzoyl hybrid cannabinoid 22, N-alkylation of which afforded target cannabinoid 4. The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of Delta(8)-THC (K-i=19.3+/-3 nM), and shows comparable potency in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00305-3

文献信息

• Synthesis and pharmacology of a hybrid cannabinoid
  作者：John W. Huffman、Jianzhong Lu、Dong Dai、Aleksandr Kitaygorodskiy、Jenny L. Wiley、Billy R. Martin

  DOI：10.1016/s0968-0896(99)00305-3

  日期：2000.2

  A pentacyclic hybrid cannabinoid (4) has been synthesized, which combines structural elements of traditional cannabinoids and cannabmimetic indoles. Cannabinoid 4 contains a 1-pentylindole structure fused to the 2,3-positions of the partially reduced hydroxydibenzopyran system of THC. The successful approach to 4 employed 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole (17) as the starting material. Dehydrogenation to carbazole 18, followed by demethylation and condensation with trans-p-menthadienol gave N-benzoyl hybrid cannabinoid 22, N-alkylation of which afforded target cannabinoid 4. The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of Delta(8)-THC (K-i=19.3+/-3 nM), and shows comparable potency in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.