5,8-dimethyl-3-methoxycarbonyl-9H-carbazole

• 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: 5,8-dimethyl-3-methoxycarbonyl-9H-carbazole
• 英文别名: methyl 5,8-dimethyl-9H-carbazole-3-carboxylate
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: TWOCLONDWOZFNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-己二醇 、 吲哚-5-甲酸甲酯 在 montmorillonite K-10 作用下， 反应 0.5h， 以79%的产率得到5,8-dimethyl-3-methoxycarbonyl-9H-carbazole
  参考文献：
  名称：

  Microwave-Assisted Solid-Acid-Catalyzed Friedel-Crafts Alkylation and Electrophilic Annulation of Indoles Using Alcohols as Alkylating Agents

  摘要：

  醇类被认为是环境友好的烷基化试剂，因为它们反应的唯一副产物是水。本文报道了利用微波辅助的Friedel-Crafts烷基化和亲电环化反应，使用醇作为烷基化试剂对吲哚进行修饰。使用叔丁醇对吲哚进行烷基化反应，得到3-取代的叔丁基吲哚。通过使用己二醇-2,5作为反应剂，可实现吲哚的亲电环化/芳构化级联反应，生成取代的咔唑。该反应由强固体酸催化剂蒙脱石K-10催化。产物获得了良好的产率和高度选择性。

  DOI：

  10.1055/s-0029-1217052

文献信息

• Solvent-Free Solid Acid-Catalyzed Electrophilic Annelations: A New Green Approach for the Synthesis of Substituted Five-Membered N-Heterocycles
  作者：Mohammed Abid、Andrew Spaeth、Béla Török

  DOI：10.1002/adsc.200606200

  日期：2006.10

  An effective microwave-induced, solid acid-catalyzed, environmentally benign synthesis of substituted pyrroles, indoles and carbazoles under solvent-free conditions is described. The new synthetic methodology is based on the use of a considerably strong solid acid, K-10 montmorillonite. Both the cyclialkylation of amines and annelation of pyrroles and indoles have been completed within minutes and

  描述了在无溶剂条件下有效的微波诱导的，固体酸催化的环境友好的取代吡咯，吲哚和咔唑的合成。新的合成方法是基于使用相当强的固体酸K-10蒙脱石。胺的环烷基化以及吡咯和吲哚的脱嵌均在数分钟内完成，并提供了优异的产率（75–98％），选择性几乎为100％。
• Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: part I
  作者：Anna Caruso、Adele Chimento、Hussein El-Kashef、Jean-Charles Lancelot、Antonella Panno、Vincenzo Pezzi、Carmela Saturnino、Maria Stefania Sinicropi、Rosa Sirianni、Sylvain Rault

  DOI：10.3109/14756366.2011.603132

  日期：2012.8.1

  Several 9H-carbazole derivatives are used for various pharmacological applications. Many of these compounds demonstrated cytotoxic and anticancer activities. In this work, we have investigated the cytotoxic activity of some substituted carbazoles against cancer cell lines (MCF-7, and ISK). The derivative 2a showed the highest inhibitory activity against both cell lines.
• Microwave-Assisted Solid-Acid-Catalyzed Friedel-Crafts Alkylation and Electrophilic Annulation of Indoles Using Alcohols as Alkylating Agents
  作者：Béla Török、Aditya Kulkarni、Phong Quang

  DOI：10.1055/s-0029-1217052

  日期：2009.12

  Alcohols are considered environmentally benign alkylating agents since the only by-product generated in their reactions is water. Herein, we report a microwave-assisted Friedel-Crafts alkylation and electrophilic annulation of indoles using alcohols as alkylating agents. Alkylation of indoles using tert-butyl alcohol gives 3-substituted tert-butylindoles. A domino electrophilic annulation/aromatization­ of indoles using hexane-2,5-diol results in the formation of substituted carbazoles. The reaction is catalyzed by a strong, solid-acid catalyst montmorillonite K-10. The products were obtained in good yields and high selectivities.

  醇类被认为是环境友好的烷基化试剂，因为它们反应的唯一副产物是水。本文报道了利用微波辅助的Friedel-Crafts烷基化和亲电环化反应，使用醇作为烷基化试剂对吲哚进行修饰。使用叔丁醇对吲哚进行烷基化反应，得到3-取代的叔丁基吲哚。通过使用己二醇-2,5作为反应剂，可实现吲哚的亲电环化/芳构化级联反应，生成取代的咔唑。该反应由强固体酸催化剂蒙脱石K-10催化。产物获得了良好的产率和高度选择性。