4,6-dichloro-3-phenylcarbamoylethynyl-indole-2-carboxylic acid methyl ester | 153436-31-8

• 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: 4,6-dichloro-3-phenylcarbamoylethynyl-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 3-(3-anilino-3-oxoprop-1-ynyl)-4,6-dichloro-1H-indole-2-carboxylate
• CAS: 153436-31-8
• 化学式: C₁₉H₁₂Cl₂N₂O₃
• 分子量: 387.222
• InChiKey: OHKAPCLENKAVMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-3-phenylcarbamoylethynyl-indole-2-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 11.0h， 以67%的产率得到4,6-dichloro-3-phenylcarbamoylethynyl-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Substituted Indole-2-carboxylates: Versatile Introduction of a Carbamoyl Moiety at the C-3 Position

  摘要：

  This paper deals with a novel and versatile synthetic approach for the introduction of a functionalized ethynyl side chain at the C-3 position of the 2-carboxyindole nucleus. The key step of this process is represented by the coupling reaction between the dianion deriving from the 2-carboxylate-3-acetylide with different isocyanates.

  DOI：

  10.1080/00397919908085936
• 作为产物：
  描述：

  4,6-dichloro-3-formyl-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester 在 1 盐酸 、 lithium hydroxide 、 叔丁基锂 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 13.5h， 生成 4,6-dichloro-3-phenylcarbamoylethynyl-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Substituted Indole-2-carboxylates: Versatile Introduction of a Carbamoyl Moiety at the C-3 Position

  摘要：

  This paper deals with a novel and versatile synthetic approach for the introduction of a functionalized ethynyl side chain at the C-3 position of the 2-carboxyindole nucleus. The key step of this process is represented by the coupling reaction between the dianion deriving from the 2-carboxylate-3-acetylide with different isocyanates.

  DOI：

  10.1080/00397919908085936

文献信息

• Indole-2-carboxylic acid derivatives
  申请人：GLAXO S.p.A.

  公开号：EP0568136A1

  公开（公告）日：1993-11-03

  The invention relates to compounds of formula (I). or a salt, or metabolically labile ester thereof wherein R represents a group selected from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, hydroxy, trifluoromethyl, trifluoromethoxy, nitro, cyano, SO₂R₁ or COR₁ wherein R₁ represents hydroxy, methoxy, or amino; m is zero or an integer 1 or 2; A represents an ethynyl group or an optionally substituted ethenyl, or cyclopropyl group; X represents -O- or NH; R₂ represents an aryl group and when X represents an oxygen atom R₂ may also represent a hydrogen atom or an alkyl group; which are antagonists of excitatory amino acids, to processes for their preparation and to their use in medicine.

  本发明涉及式 (I) 化合物。 其中 R 代表选自卤素、烷基、烷氧基、氨基、烷基氨基、二烷基氨基、羟基、三氟甲基、三氟甲氧基、硝基、氰基、SO₂R₁ 或 COR₁ 的基团，其中 R₁ 代表羟基、甲氧基或氨基；m 为零或 1 或 2 的整数； A 代表乙炔基或任选取代的乙烯基或环丙基； X 代表-O-或 NH； R₂代表芳基，当 X 代表氧原子时，R₂也可以代表氢原子或烷基。
• US5374648A
  申请人：——

  公开号：US5374648A

  公开（公告）日：1994-12-20
• Synthesis of Substituted Indole-2-carboxylates: Versatile Introduction of a Carbamoyl Moiety at the C-3 Position
  作者：Simone A. Giacobbe、Romano Di Fabio、Davide Baraldi、Alfredo Cugola、Daniele Donati

  DOI：10.1080/00397919908085936

  日期：1999.9

  This paper deals with a novel and versatile synthetic approach for the introduction of a functionalized ethynyl side chain at the C-3 position of the 2-carboxyindole nucleus. The key step of this process is represented by the coupling reaction between the dianion deriving from the 2-carboxylate-3-acetylide with different isocyanates.