ethyl 3-amino-7-cyano-1,6-dimethyl-4-(trifluoromethyl)-1H-indole-2-carboxylate | 853052-90-1

• 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: ethyl 3-amino-7-cyano-1,6-dimethyl-4-(trifluoromethyl)-1H-indole-2-carboxylate
• 英文别名: Ethyl 3-amino-7-cyano-1,6-dimethyl-4-(trifluoromethyl)indole-2-carboxylate；ethyl 3-amino-7-cyano-1,6-dimethyl-4-(trifluoromethyl)indole-2-carboxylate
• CAS: 853052-90-1
• 化学式: C₁₅H₁₄F₃N₃O₂
• 分子量: 325.29
• InChiKey: BJBMTWKNEDCFBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-7-cyano-1,6-dimethyl-4-(trifluoromethyl)-1H-indole-2-carboxylate 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 2.0h， 以78%的产率得到3-amino-7-(aminocarbonyl)-1,6-dimethyl-4-(trifluoromethyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Regioselective cyclization of unsymmetrical dicyanoanilines to novel 2,3-bifunctionalised indole regioisomers and their use in the synthesis of 4,5-dihydro[1,3]oxazino[5,4-b]indole-6-carbonitriles

  摘要：

  Synthesis of novel-2,3-bifunetionalised indole regioisomers (2/3 and 6/7) from unsymmetrical dicyanoanilines 1 by regioselective cyclization in two independent ways. Regioisomers 6 are further utilized in synthesis of novel 4,5-dihydro[1,3]oxazino[5,4-b] indole-6-carbonitriles 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.046
• 作为产物：
  描述：

  2-iodo-4-methyl-6-(trifluoromethyl)isophthalonitrile 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 ethyl 3-amino-7-cyano-1,6-dimethyl-4-(trifluoromethyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Regioselective cyclization of unsymmetrical dicyanoanilines to novel 2,3-bifunctionalised indole regioisomers and their use in the synthesis of 4,5-dihydro[1,3]oxazino[5,4-b]indole-6-carbonitriles

  摘要：

  Synthesis of novel-2,3-bifunetionalised indole regioisomers (2/3 and 6/7) from unsymmetrical dicyanoanilines 1 by regioselective cyclization in two independent ways. Regioisomers 6 are further utilized in synthesis of novel 4,5-dihydro[1,3]oxazino[5,4-b] indole-6-carbonitriles 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.046

文献信息

• Synthesis and Anticancer Activity of Novel Amide Tagged Trifluoromethyl Indole and Pyrimido Indole Derivatives
  作者：Manoj Kumar Mandadi、Ramana Reddy Bobbala、Balakrishna Kolli、Rambabu Gundla

  DOI：10.14233/ajchem.2021.23313

  日期：——

  of novel amide tagged trifluoromethyl indole and pyrimido indole derivatives 4a-e & 5a-e and 6a-d & 7a-d were synthesized from 4-methyl-2-(methylamino)-6-(trifluoromethyl)isophthalonitrile (1) on reaction with bromoethyl acetate to obtain 2a and 2b isomers. Compound 2a treated with hydrazine hydrate followed by Schiff base reaction to get compounds 4a-e. In another way, compound 2a on reaction with

  以 4-甲基-2-(甲氨基)-6-(三氟甲基)间苯二甲腈 (1) 为原料，合成了一系列新型酰胺标记的三氟甲基吲哚和嘧啶吲哚衍生物 4a-e & 5a-e 和 6a-d & 7a-d与溴乙酸乙酯反应，得到2a和2b异构体。化合物2a用水合肼处理，然后进行希夫碱反应，得到化合物4a-e。另一种方式，化合物2a与脂肪族伯胺反应得到化合物6a-d。为了环化，用三氟乙酸处理化合物4a-e和6a-d，分别得到化合物5a-e和7a-d。所有合成的化合物 4a-e 和 5a-e 以及 6a-d 和 7a-d 均测试了对四种人类癌细胞系的抗癌活性，例如 A549-肺癌 (CCL-185)、MCF7-乳腺癌 (HTB-22) )、DU145-前列腺癌 (HTB-81) 和 HeLa-宫颈癌 (CCL-2)。发现化合物 9e 和 9f 在微摩尔浓度下具有良好的抗癌活性。
• Regioselective cyclization of unsymmetrical dicyanoanilines to novel 2,3-bifunctionalised indole regioisomers and their use in the synthesis of 4,5-dihydro[1,3]oxazino[5,4-b]indole-6-carbonitriles
  作者：D. Maitraie、G. Venkat Reddy、V.V.V.N.S. Rama Rao、S. Ravikanth、B. Narsaiah、P. Shanthan Rao、K. Ravikumar、B. Sridhar

  DOI：10.1016/j.tet.2005.02.046

  日期：2005.4

  Synthesis of novel-2,3-bifunetionalised indole regioisomers (2/3 and 6/7) from unsymmetrical dicyanoanilines 1 by regioselective cyclization in two independent ways. Regioisomers 6 are further utilized in synthesis of novel 4,5-dihydro[1,3]oxazino[5,4-b] indole-6-carbonitriles 9. (c) 2005 Elsevier Ltd. All rights reserved.