2-(2-bromophenyl)-5-methyl-1H-indole | 899694-59-8

• 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: 2-(2-bromophenyl)-5-methyl-1H-indole
• CAS: 899694-59-8
• 化学式: C₁₅H₁₂BrN
• 分子量: 286.171
• InChiKey: VECROWKNCMCPCU-UHFFFAOYSA-N

物化性质

• 沸点：
  434.5±30.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-5-methyl-1H-indole 在 盐酸 、 palladium diacetate 、 caesium carbonate 、 双(2-二苯基磷苯基)醚 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 2-methyl-6H-isoindolo[2,1-a]indol-6-one
  参考文献：
  名称：

  Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: an investigation of Pd-catalyzed isocyanide insertion

  摘要：

  A novel Pd-catalyzed intramolecular cyclization via tert-butyl isocyanide insertion from 2-(2-bromophenyl)-1H-indoles has been developed, which demonstrates the utility of isocyanides in C-N or C-C bond construction. Treatment of 2-(2-bromophenyl)-1H-indoles with tert-butyl isocyanide affords 6H-isoindolo[2,1-a]indol-6-ones with high efficiency. However, N-methyl or N-Boc protected 2-(2-bromophenyl)-1H-indoles gives indenoindolones in excellent yields under the same condition, which reveals that under the described situation, isocyanides insertion for the formation of C-N bonds is prior to that of C-C bonds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.018
• 作为产物：
  描述：

  4-甲基苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(2-bromophenyl)-5-methyl-1H-indole
  参考文献：
  名称：

  二苯基氧化膦吲哚的直接铜催化 C-3 芳基化

  摘要：

  我们开发了一种简单有效的方法，用于在温和条件下在 CuI 存在下对含磷吲哚化合物进行 C-3 芳基化。该反应为配体的修饰提供了可靠的方法。

  DOI：

  10.1055/a-1633-8792

文献信息

• Copper-Catalyzed Cascade Synthesis of 1<i>H</i>-Indolo[1,2-<i>c</i>]quinazoline Derivatives
  作者：Hao Zhang、Yibao Jin、Hongxia Liu、Yuyang Jiang、Hua Fu

  DOI：10.1002/ejoc.201200953

  日期：2012.12

  A simple, efficient and practical approach to 1H-indolo[1,2-c]quinazoline derivatives has been developed that uses inexpensive and readily-available catalyst and substrates. The method should provide a new strategy for N-fused heterocycles and will show wide application in organic chemistry and medicinal chemistry.

  已经开发了一种简单、有效和实用的 1H-吲哚[1,2-c] 喹唑啉衍生物方法，该方法使用廉价且易于获得的催化剂和底物。该方法将为N-稠合杂环提供一种新的策略，并将在有机化学和药物化学中显示出广泛的应用。
• Synthesis of Indolo[2,1-a]isoquinolines via Copper-Catalyzed C–C Coupling and Cyclization of 2-(2-Bromoaryl)-1H-indoles with 1,3-Diketones
  作者：Chan Cho、Ha Lee、Pham Dao、Young-su Kim

  DOI：10.1055/s-0036-1591589

  日期：2018.8

  Abstract 2-(2-Bromoaryl)-1H-indoles are coupled and cyclized with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic amount of copper(I) iodide along with a base to afford the corresponding indolo[2,1-a]isoquinolines in moderate to good yields. 2-(2-Bromoaryl)-1H-indoles are coupled and cyclized with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic

  摘要 通过在催化量的碘化亚铜（I）和碱存在下，在DMF中微波辐射，将2-（2-溴芳基）-1 H-吲哚偶联并与1,3-二酮环合，得到相应的吲哚[ 2,1- a ]异喹啉的产量中等至良好。 通过在催化量的碘化亚铜（I）和碱存在下，在DMF中微波辐射，将2-（2-溴芳基）-1 H-吲哚偶联并与1,3-二酮环合，得到相应的吲哚[ 2,1- a ]异喹啉的产量中等至良好。
• Nickel-Catalyzed Cyclization Strategy for the Synthesis of Pyrroloquinolines, Indoloquinolines, and Indoloisoquinolines
  作者：Sampath Thavaselvan、Kanniyappan Parthasarathy

  DOI：10.1021/acs.orglett.0c01055

  日期：2020.5.15

  An inexpensive and benchtop stable Ni-catalyst/Zn system for the synthesis of pyrrolo/indoloquinolines and indolo[2,1-a]isoquinolines is explored. This platform provides a one-pot entry for the preparation of various pyrrolo and indoloquinolines/isoquinolines, which involves successive C-C and C-N bond formation, respectively. In addition, we have also performed the preliminary photophysical studies

  探索了一种廉价且台式稳定的镍催化剂/锌体系，用于合成吡咯并/吲哚并喹啉和吲哚并[2,1-a]异喹啉。该平台为制备各种吡咯啉和吲哚喹啉/异喹啉提供了一个一站式方法，分别涉及连续的CC和CN键形成。此外，我们还对合成的化合物进行了初步的光物理研究。
• General and efficient copper-catalyzed aerobic oxidative synthesis of N-fused heterocycles using amino acids as the nitrogen source
  作者：Qing Liu、Haijun Yang、Yuyang Jiang、Yufen Zhao、Hua Fu

  DOI：10.1039/c3ra41644e

  日期：——

  efficient copper-catalyzed aerobic oxidative method for the synthesis of N-fused heterocycles has been developed by using readily available α-amino acids as the nitrogen source. The reactions underwent N-arylation, aerobic oxidative dehydrogenation, intramolecular cyclization and dissociation of formic acid. This method should provide a general and practical strategy for the construction of N-fused

  通过使用容易获得的α-氨基酸作为氮源，已经开发了用于合成N-稠合杂环的通用且有效的铜催化的需氧氧化方法。反应进行了N-芳基化，好氧氧化脱氢，分子内环化和C的解离甲酸。该方法应为构建N-稠合杂环提供通用和实用的策略。
• Copper-catalyzed synthesis of benzocarbazoles via α-C-arylation of ketones
  作者：Ruilong Xie、Yun Ling、Hua Fu

  DOI：10.1039/c2cc36403d

  日期：——

  A simple and efficient copper-catalyzed method for the synthesis of 11H-benzo[a]carbazoles has been developed. The protocol uses readily available substituted 2-(2-bromophenyl)-1H-indoles and ketones as starting materials and an inexpensive catalyst system. The corresponding 11H-benzo[a]carbazoles were obtained in moderate to excellent yields.

  已开发出一种简单高效的铜催化法合成11H-苯并[a]喹唑。该方案采用易得的取代2-(2-溴苯基)-1H-吲哚和酮作为起始材料，并使用廉价的催化剂系统。相应的11H-苯并[a]喹唑以中等到优异的产率得到。