6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole | 4329-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole
• 英文别名: 5,6,7,8-tetrahydro-γ-carbolin；6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole；6,7,8,9-Tetrahydro-5H-pyrido[4,3-b]indol；6,7,8,9-Tetrahydro-γ-carbolin
• CAS: 4329-69-5
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: OPSBNIJCFIELHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole 在 palladium on activated carbon 作用下， 以 二苯醚 为溶剂， 反应 0.66h， 以77%的产率得到5H-吡啶并[4,3-b]吲哚
  参考文献：
  名称：

  A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

  摘要：

  A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alpha-carboline (1).

  DOI：

  10.1021/acs.joc.7b00323
• 作为产物：
  描述：

  1-(4-喹啉基)甲胺 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 palladium on activated carbon 、 氢气 、 铜 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 22.25h， 生成 6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

  摘要：

  A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alpha-carboline (1).

  DOI：

  10.1021/acs.joc.7b00323

文献信息

• [EN] TETRAHYDROCARBOLINE DERIVATIVES AS EG5 INHIBITORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDROCARBOLINE COMME INHIBITEURS DE L'EG5
  申请人：SANOFI SA

  公开号：WO2011084439A1

  公开（公告）日：2011-07-14

  The present invention relates to substituted tetrahydro-β-carbolines and substituted tetrahydro-γ-carbolines. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are inhibitors of Eg5 kinesin. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of diseases.

  本发明涉及替代的四氢-β-咔啉和替代的四氢-γ-咔啉。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是Eg5肌动蛋白的抑制剂。因此，本发明的化合物在药物制剂中具有用途，特别是在治疗和/或预防疾病方面。
• Rapid and Efficient Microwave-Assisted Synthesis of 4-, 5-, 6- and 7-Azaindoles
  作者：Nicolas Lachance、Myriam April、Marc-André Joly

  DOI：10.1055/s-2005-872100

  日期：——

  imines/ enamines formed between aminopyridines and ketones are converted in moderate to good yields to the corresponding 4-, 5-, 6- or 7-azaindoles via the Hegedus-Mori-Heck reaction (intramolecular Heck reaction). A systematic examination of all isomeric azaindoles synthesis revealed this one-pot procedure to be general in scope.

  在微波辐照条件下，氨基吡啶和酮之间形成的亚胺/烯胺通过 Hegedus-Mori-Heck 反应（分子内 Heck 反应）以中等至良好的产率转化为相应的 4-、5-、6-或 7-氮杂吲哚。对所有异构氮杂吲哚合成的系统检查表明，这种一锅法在范围上是通用的。
• Mann et al., Journal of the Chemical Society, 1959, p. 3830,3832
  作者：Mann et al.

  DOI：——

  日期：——
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  作者：Plutitskii, D. N.、Smushkevich, Yu. I.、Mulyashov, S. A.、Sapunov, V. N.、Suvorov, N. N.、et al.

  DOI：——

  日期：——
• Plutitskii, D. N.; Smushkevich, Yu. I.; Suvorov, N. N., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1395 - 1397
  作者：Plutitskii, D. N.、Smushkevich, Yu. I.、Suvorov, N. N.

  DOI：——

  日期：——