4-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester | 1061215-05-1

• 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: 4-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 4-bromo-5,6-dimethoxy-1H-indole-2-carboxylate
• CAS: 1061215-05-1
• 化学式: C₁₂H₁₂BrNO₄
• 分子量: 314.136
• InChiKey: BUNFVVSTYXMLQF-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188 °C
• 沸点：
  426.6±40.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

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：

  4-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以85%的产率得到4-BroMo-5,6-diMethoxy-1H-indole-2-carboxylic acid
  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
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 在 硫酸 、 MoO₂Cl₂(dmf)2 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 19.0h， 生成 4-Bromo-5,6-dimethoxy-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  简洁，高效，实用的溴5,6-二甲氧基吲哚构建基块的组装

  摘要：

  描述了一种简洁，有效且简单的方法来制备一系列溴吲哚结构单元。邻硝基肉桂酸酯中间体的无纯化制备和干净的改性Cadogan吲哚合成物突显了合成路线。吲哚合成的范围已通过使用各种溶剂和易于除去的膦试剂进行了探索和扩展。

  DOI：

  10.1016/j.tetlet.2011.01.076

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.
• Expedient routes to valuable bromo-5,6-dimethoxyindole building blocks
  作者：Paul B. Huleatt、Sze Shiong Choo、Sheena Chua、Christina L.L. Chai

  DOI：10.1016/j.tetlet.2008.06.080

  日期：2008.9

  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.
• Concise, efficient and practical assembly of bromo-5,6-dimethoxyindole building blocks
  作者：Paul B. Huleatt、Jacelyn Lau、Sheena Chua、Yun Lei Tan、Hung Anh Duong、Christina L.L. Chai

  DOI：10.1016/j.tetlet.2011.01.076

  日期：2011.3

  A concise, efficient and simple route to a series of bromoindole building blocks is described. The synthetic routes are highlighted by purification-free preparation of o-nitrocinnamate intermediates and clean, modified Cadogan indole syntheses. The scope of this indole synthesis has been explored and expanded through the use of a range of solvents and easily removable phosphine reagents.

  描述了一种简洁，有效且简单的方法来制备一系列溴吲哚结构单元。邻硝基肉桂酸酯中间体的无纯化制备和干净的改性Cadogan吲哚合成物突显了合成路线。吲哚合成的范围已通过使用各种溶剂和易于除去的膦试剂进行了探索和扩展。