2-bromo-5-methoxy-1H-indole | 169383-96-4

• 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: 2-bromo-5-methoxy-1H-indole
• CAS: 169383-96-4
• 化学式: C₉H₈BrNO
• 分子量: 226.073
• InChiKey: DNYRJWVXPHDSBY-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C (decomp)
• 沸点：
  355.6±22.0 °C(Predicted)
• 密度：
  1.591±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-5-methoxy-1H-indole 在 dihydroxyborane 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-甲氧基吲哚
  参考文献：
  名称：

  Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies

  摘要：

  A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared. The optimized inhibitors possess single digit nanomolar activity against p110 alpha (PI3K-alpha), good pharmaceutical properties, selectivity versus p110 gamma (PI3K-gamma), and tunable selectivity versus the mammalian target of rapamycin ( mTOR). Modeling of compounds 9 and 32 in homology models of PI3K-alpha and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.082
• 作为产物：
  描述：

  2-(2,2‐dibromovinyl)‐4‐methoxyaniline 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tri-tert-butylphosphonium tetrafluoroborate 作用下， 以 甲苯 为溶剂， 以66%的产率得到2-bromo-5-methoxy-1H-indole
  参考文献：
  名称：

  Intramolecular cross-coupling of gem-dibromoolefins: a mild approach to 2-bromo benzofused heterocycles

  摘要：

  采用温和的无配体铜催化交叉偶联程序，从容易获得的二溴烯烃中制备出了非常有用的卤代苯并呋喃和苯并噻吩。

  DOI：

  10.1039/b912093a

文献信息

• Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions
  作者：Min Wang、Pinhua Li、Wei Chen、Lei Wang

  DOI：10.1039/c4ra00603h

  日期：——

  2-Bromo(chloro)indoles were readily prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions.

  2-溴（氯）吲哚可通过TBAF促进的2-（gem-二溴（氯）乙烯）苯胺的分子内环化反应，在无金属和微波辐射条件下，以极高的产率轻松制备。
• Practical Synthesis of Chromeno[2,3-<i>b</i>]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy
  作者：Jianming Liu、Na Liu、Yuanyuan Yue、Yanyan Wang、Kaige Chen、Jia Zhang、Shufang Zhao、Kelei Zhuo

  DOI：10.1002/asia.201601681

  日期：2017.2.16

  The synthesis of chromeno[2,3‐b]indole from simple starting materials remains a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis of the product could be achieved

  由简单的起始原料合成苯并[2,3-b]吲哚仍然是一个艰巨的过程。在此，2-溴吲哚经历了水杨醛的亲核攻击，随后在分子内插入醛基并进行芳构化以生成所需的chromeno [2,3- b ]吲哚。此外，可以容忍各种官能团，并且在最佳条件下可以实现克级的产物合成。
• Heteroaryl radicals in synthesis: Radical cyclisation reactions of 2-bromoindoles
  作者：Adrian P. Dobbs、Keith Jones、Ken T. Veal

  DOI：10.1016/s0040-4020(97)10423-9

  日期：1998.3

  The synthesis and radical cyclisations of 2-bromoindoles carrying an unsaturated N-alkyl group is described.

  描述了带有不饱和N-烷基的2-溴吲哚的合成和自由基环化。
• Indole radical cyclisations: a rapid route to mitosenes
  作者：Adrian P. Dobbs、Keith Jones、Ken T. Veal

  DOI：10.1016/0040-4039(95)00838-4

  日期：1995.7

  The syntheses and radical cyclisations of 2-bromoindoles carrying an unsaturated N-alkyl group is described.

  描述了带有不饱和N-烷基的2-溴吲哚的合成和自由基环化。
• Halogen–Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate
  作者：Qingqiang Tian、Suqin Shang、Huajun Wang、Guoqiang Shi、Zhiyao Li、Jianyong Yuan

  DOI：10.3390/molecules22111952

  日期：——

  bromine-metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination of i-PrMgCl and n-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen-lithium exchange, but also

  通过对现有方案的简单修改，开发了在非低温条件下在带有酸性质子的带有取代基的溴杂环上进行的选择性实用溴金属交换。我们将i-PrMgCl和n-BuLi结合使用的方案不仅解决了分子间淬灭的问题，这种问题通常在单独使用烷基锂作为卤素-锂交换试剂时发生，而且还提供了一种高度选择性的溴化方法。通过螯合作用在二溴芳烃化合物上进行金属交换。