1-(3,5-二甲基苯基)吲哚-5-胺 | 360045-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(3,5-二甲基苯基)吲哚-5-胺
• 英文名称: 1-(3,5-dimethylphenyl)-5-aminoindole
• 英文别名: 1H-Indol-5-amine, 1-(3,5-dimethylphenyl)-；1-(3,5-dimethylphenyl)indol-5-amine
• CAS: 360045-07-4
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: VMJINDHDVAPUTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,5-二甲基苯基)吲哚-5-胺 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 生成 1-(3,5-Dimethylphenyl)-2,3-dihydroindol-5-amine
  参考文献：
  名称：

  Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide

  摘要：

  A series of substituted indoline and indole derivatives with cyclooxygenase (COX)-inhibitory activity was prepared during our structural development studies based on thalidomide as a multi-template lead compound. Structure-activity relationship studies indicated that the nature of the substituent introduced at the benzene ring of the indoline (indole) backbone, and the length and type of the linking group between the nitrogen atom of indoline (indole) and the N-substituent are important for the activity. This study has led to the identification of COX-1-selective inhibitors, and these should be useful not only as pharmacological tools to investigate the physiology and pathophysiology of COX, but also as sophisticated leads for the development of novel drugs to treat COX-associated diseases, such as inflammatory diseases, and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.002
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium on activated charcoal 3 A molecular sieve 、 氢气 、 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 1-(3,5-二甲基苯基)吲哚-5-胺
  参考文献：
  名称：

  Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide

  摘要：

  A series of substituted indoline and indole derivatives with cyclooxygenase (COX)-inhibitory activity was prepared during our structural development studies based on thalidomide as a multi-template lead compound. Structure-activity relationship studies indicated that the nature of the substituent introduced at the benzene ring of the indoline (indole) backbone, and the length and type of the linking group between the nitrogen atom of indoline (indole) and the N-substituent are important for the activity. This study has led to the identification of COX-1-selective inhibitors, and these should be useful not only as pharmacological tools to investigate the physiology and pathophysiology of COX, but also as sophisticated leads for the development of novel drugs to treat COX-associated diseases, such as inflammatory diseases, and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.002

文献信息

• Expanding Pd-Catalyzed C−N Bond-Forming Processes:  The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions
  作者：Xiaohua Huang、Kevin W. Anderson、Danilo Zim、Lei Jiang、Artis Klapars、Stephen L. Buchwald

  DOI：10.1021/ja035483w

  日期：2003.6.1

  The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been

  Pd催化芳基甲苯磺酸酯和苯磺酸酯胺化的第一种通用方法是利用配体1开发的，该配体属于新一代联芳基单膦配体。此外，新的催化剂系统首次实现了芳基芳烃磺酸盐的酰胺化和不需要使用助溶剂的水性胺化方案。底物范围已显着扩大到包括含有伯酰胺和游离羧酸基团的芳基卤化物。在多功能基板的情况下，Pd 催化的胺化可以提供与 Cu 催化的 CN 键形成过程互补的选择性。
• Ligands for metals and improved metal-catalyzed processes based thereon
  申请人：——

  公开号：US20040171833A1

  公开（公告）日：2004-09-02

  One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

  本发明的一个方面涉及过渡金属配体。本发明的第二个方面涉及在过渡金属催化的碳-杂原子和碳-碳键形成反应中使用包含这些配体的催化剂。所述方法提供了过渡金属催化反应的许多特征的改进，包括适用底物的范围、反应条件和效率。
• Cyclic phenyl-substituted indazols, a process for their production and their use as anti-inflammatory agents
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1917963A1

  公开（公告）日：2008-05-07

  The present invention relates to the compounds of formula I, processes for their production and their use as anti-inflammatory agents.

  本发明涉及公式I的化合物，其制备方法以及它们作为抗炎药物的用途。
• Indole and indazole derivatives as anti-inflammatory agents
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1921067A1

  公开（公告）日：2008-05-14

  The present invention relates to the compounds of formula I, processes for their production and their use as anti-inflammatory agents.

  本发明涉及式I的化合物，其制备过程及其作为抗炎剂的用途。
• LINEAR PHENYL-SUBSTITUTED INDAZOLES AND INDOLES, A PROCESS FOR THEIR PRODUCTION AND THEIR USE AS ANTI-INFLAMMATORY AGENTS
  申请人：Berger Markus

  公开号：US20080188666A1

  公开（公告）日：2008-08-07

  The present invention relates to the compounds of formula I, processes for their production and their use as anti-inflammatory agents.

  本发明涉及式I的化合物，其制备过程以及它们作为抗炎药物的用途。