3-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester | 15794-39-5

• 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-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 3-bromo-5,6-dimethoxy-1H-indole-2-carboxylate
• CAS: 15794-39-5
• 化学式: C₁₂H₁₂BrNO₄
• 分子量: 314.136
• InChiKey: FBECDHUEKOTRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester 在 四(三苯基膦)钯 lithium hydroxide 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3-Benzo[1,3]dioxol-5-yl-1-benzo[1,3]dioxol-5-ylmethyl-5,6-dimethoxy-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  1,3-diaryl-2-carboxyindoles as potent non-peptide endothelin antagonists

  摘要：

  Endothelin-1 is a potent vasoconstrictor that is thought to be involved in many human disease states. We have developed a series of indole non-peptide endothelin antagonists including PD 159110 (31), an ET(A) selective antagonist, and PD 159020 (37), a non-selective ET(A)/ET(B) antagonist. The discovery, synthesis, and structure-activity relationships of this series of compounds are described. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00170-9
• 作为产物：
  描述：

  5,6-二甲氧基吲哚-2-羧酸甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到3-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Expedient routes to valuable bromo-5,6-dimethoxyindole building blocks

  摘要：

  The synthesis of 3-, 4-, 7-bromo and 4,7-dibrominated 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derivatives is reported. Hemetsberger and Bartoli indole syntheses were investigated and expedient routes to the desired compounds were developed. These indoles are valuable substrates for elaboration using transition metal-mediated cross-coupling chemistry. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.080

文献信息

• Synthesis of Biindolyls via Palladium-Catalyzed Reactions
  作者：Hung A. Duong、Sheena Chua、Paul B. Huleatt、Christina L. L. Chai

  DOI：10.1021/jo801846b

  日期：2008.11.21

  An unprecedented synthesis of a range of high value homo-and heterobiindolyls is presented. The one-pot Miyaura borylation and subsequent Suzuki-Miyaura coupling sequence allows for the construction of the highly sterically congested C-C bond between two bromoindoles in modest to good overall yields.