2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine | 99131-94-9

• 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: 2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine
• 英文别名: 2-(2-Aminoethyl)-1,2,3,4,9-tetrahydrocarbazole；2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethanamine
• CAS: 99131-94-9
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: MEZXTQPMHGJMGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine 在 sodium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-b]indole Framework of the Uleine and Strychnos Alkaloids

  摘要：

  The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 Can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

  DOI：

  10.1021/jo302132d
• 作为产物：
  描述：

  2-[4-(2-Nitrophenyl)-5-oxocyclohex-3-en-1-yl]acetonitrile 在 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 66.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以87%的产率得到2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine
  参考文献：
  名称：

  A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-b]indole Framework of the Uleine and Strychnos Alkaloids

  摘要：

  The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 Can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

  DOI：

  10.1021/jo302132d

文献信息

• Studies on the synthesis of pentacyclic strychnos indole alkaloids. photocyclization of n-chloroacetyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole derivatives
  作者：Joan Bosch、Mercedes Amat、Enric Sanfeliu、Miguel Angel Miranda

  DOI：10.1016/s0040-4020(01)96651-7

  日期：1985.1

  give a 1 ,2 ,3 ,4 , 5 ,6-hexahydro-2 ,11-ethano-1 ,5-methanoazocino [4 , 3-6] indole system. Consequently, the method appears to be unsuitable for constructing the pyrrolidine ring of pentacyclic Strychnos indole alkaloids.

  在吲哚的4-位上发生2-氯乙酰基-1,2,3,4,5,6-六氢-1,5-甲亚偶氮并[4,3-b]吲哚（）的光环化反应，得到1,2， 3，4，5，6-六氢-2，11-乙基-1，5-甲亚氮并[4，3-6]吲哚体系。因此，该方法似乎不适用于构建五环马兜铃吲哚生物碱的吡咯烷环。
• Structural, electronic, and spectroscopic study on 1,5-methanoazocino[4,3-b]indole synthesized by TFB-based route
  作者：Goncagül Serdaroğlu、Nesimi Uludağ

  DOI：10.1007/s11696-021-01683-y

  日期：——

  This work proposed a new route to synthesizing pharmaceutical important molecules just in three steps. This synthetic route provides an economical way for synthetic chemistry to get the key products concerning the biochemical importance economically including the monoterpene alkaloids, uleine, tubifolidine. This route involves ring closure and the reaction also involved a cyclization reaction tetrahydrocarbazole

  这项工作提出了一条只需三个步骤即可合成药物重要分子的新途径。该合成路线为合成化学以经济的方式获得具有生化重要性的关键产品包括单萜生物碱、脲碱、烟花碱等提供了一种经济的途径。该路线涉及闭环，该反应还涉及环化反应四氢咔唑在 C-2 位具有胺侧链，并且该环化由四氟-1,4-苯醌 (TFB) 介导。在提议的基于 TFB 的路线中，(4) (2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine), (5) 2,3,4,5, 6,7-hexahydro-1H-1,5-methanoazocino[4,3-b]indole, (6) 甲基 (1R,5S)-1,3,4,5,6,7-hexahydro-2H-1, 5-methanoazocino[4,3-b]indole-2-carboxylate, (7) 甲基 (1R,5S)-6-oxo-1,3,4,5
• An Improved Approach to the Synthesis of Tetracyclic 20-Deethyl-4-demethyldasycarpidone and 20-Deethyldasycarpidone
  作者：N. Uludag、H. Mutlu

  DOI：10.1134/s1070428022090111

  日期：2022.9

  been reported for the synthesis of 20-deethyl-4-demethyldasycarpidone and 20-deethyldasycarpidone by tetracholoro-1,4-benzoquinone (TCB)-mediated cyclization of intermediate tetrahydrocarbazole obtained from tert-butyl [2-methyl-1-(4-methylbenzenesulfonyl)-1H-indol-3-yl]methyl carbonate. 2-[9-(4-Methylbenzenesulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]acetonitrile as the ABCD sub­struc­ture of Strychnos

  摘要 报道了一种通过四氯-1,4-苯醌 (TCB) 介导的由叔丁基 [2-甲基-1- (4-甲基苯磺酰基)-1 H-吲哚-3-基]碳酸甲酯。2-[9-(4-Methylbenzosulfonyl)-2,3,4,9-tetrahydro-1 H -carbazol-2-yl]乙腈作为马钱子生物碱家族的ABCD亚结构首次以不同的方式合成.
• A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-<i>b</i>]indole Framework of the Uleine and <i>Strychnos</i> Alkaloids
  作者：Tristan A. Reekie、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/jo302132d

  日期：2012.12.7

  The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 Can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.