3-(2,2-diethoxyethyliminomethyl)-1,4,9-trimethylcarbazole | 18073-26-2

• 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: 3-(2,2-diethoxyethyliminomethyl)-1,4,9-trimethylcarbazole
• 英文别名: 3-<2,2-Diethoxyethyl-iminomethyl>-1,4,9-trimethyl-carbazol；3-(2,2-Diethoxyethyliminomethyl)-1,4,9-trimethyl-carbazol；3-(2,2-Diethoxyethyl-iminomethyl)-1,4,9-trimethyl-carbazol；N-(2,2-diethoxyethyl)-1-(1,4,9-trimethylcarbazol-3-yl)methanimine
• CAS: 18073-26-2
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: GVXJBLAVGLVBRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,2-diethoxyethyliminomethyl)-1,4,9-trimethylcarbazole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-(2,2-diethoxyethylaminomethyl)-1,4,9-trimethylcarbazole
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032
• 作为产物：
  描述：

  吲哚 在 sodium hydride 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.25h， 生成 3-(2,2-diethoxyethyliminomethyl)-1,4,9-trimethylcarbazole
  参考文献：
  名称：

  1,4-二甲基咔唑的Vilsmeier-Haack甲酰化修饰及其在玫瑰树碱合成中的应用

  摘要：

  提出了一种制备玫瑰树碱关键中间体3-甲酰基-1,4-二甲基咔唑的改进方法。修改了Vilsmeier-Haack反应的条件，以促进生产作为主要产品的3-甲酰基-1,4-二甲基咔唑，使玫瑰树碱的总产率从3％提高到14％。这种方法也适用于6-甲基玫瑰树碱和9-甲氧基玫瑰树碱的合成。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.598

文献信息

• Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives
  作者：Ryota Mori、Asako Kato、Kousuke Komenoi、Haruaki Kurasaki、Touru Iijima、Masashi Kawagoshi、Y.B. Kiran、Sho Takeda、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.ejmech.2014.05.032

  日期：2014.7

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Modifications to the Vilsmeier-Haack formylation of 1,4-dimethylcarbazole and its application to the synthesis of ellipticines
  作者：Fiona M. Deane、Charlotte M. Miller、Anita R. Maguire、Florence O. McCarthy

  DOI：10.1002/jhet.598

  日期：2011.7

  An improved method for the preparation of 3‐formyl‐1,4‐dimethylcarbazole, a key intermediate in the synthesis of ellipticine, is presented. Conditions of the Vilsmeier‐Haack reaction have been modified to facilitate the production of 3‐formyl‐1,4‐dimethylcarbazole as a major product leading to an overall improvement in yield of ellipticine from 3% to 14%. This approach was also applied to the synthesis

  提出了一种制备玫瑰树碱关键中间体3-甲酰基-1,4-二甲基咔唑的改进方法。修改了Vilsmeier-Haack反应的条件，以促进生产作为主要产品的3-甲酰基-1,4-二甲基咔唑，使玫瑰树碱的总产率从3％提高到14％。这种方法也适用于6-甲基玫瑰树碱和9-甲氧基玫瑰树碱的合成。J.杂环化​​学。（2011）。