1-Phenyl-2-brom-3-formylindol | 68770-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-Phenyl-2-brom-3-formylindol
• 英文别名: 2-bromo-1-phenyl-indole-3-carbaldehyde；2-Bromo-1-phenylindole-3-carbaldehyde
• CAS: 68770-85-4
• 化学式: C₁₅H₁₀BrNO
• 分子量: 300.154
• InChiKey: JQWMCLVPXJARLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Phenyl-2-brom-3-formylindol 在 水 、 重水 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 12.0h， 生成 2-(2-oxo-2-phenylethyl-D₂)-1-phenyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

  摘要：

  Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. gamma-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.

  DOI：

  10.1021/acs.orglett.9b01649
• 作为产物：
  描述：

  N-苯基吲哚酮 、 N,N-二甲基甲酰胺 在 三溴氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 1-Phenyl-2-brom-3-formylindol
  参考文献：
  名称：

  Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

  摘要：

  Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. gamma-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.

  DOI：

  10.1021/acs.orglett.9b01649

文献信息

• Transition-Metal-Free Access to Pyridocarbazoles from 2-Alkynylindole-3-carbaldehydes via Azomethine Ylide
  作者：Shalini Verma、Pawan K. Mishra、Manoj Kumar、Souvik Sur、Akhilesh K. Verma

  DOI：10.1021/acs.joc.8b00980

  日期：2018.6.15

  An efficient approach for the synthesis of functionalized tetrahydro-pyrido/quinolinocarbazoles from 2-alkynylindole-3-carbaldehydes and l-proline utilizing a metal-free decarboxylative cyclization, ring expansion, and ring contraction strategy via the generation of azomethine ylide was developed. The reaction of 2-alkynylindole-3-carbaldehydes with l-thioproline leads to the formation of γ-carbolines

  开发了一种有效的方法，该方法利用无金属的脱羧环化，环的扩展和环的收缩策略，通过偶氮甲meth内酯的生成，由2-炔基吲哚-3-甲醛和1-脯氨酸合成功能化的四氢吡啶基/喹啉咔唑。2-炔基吲哚-3-甲醛与1-硫代脯氨酸的反应导致形成γ-咔啉。借助于这种方便的方法，可以有效地合成多种生物活性的杂环咔唑。
• MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
  申请人：Merck Patent GmbH

  公开号：US20220177478A1

  公开（公告）日：2022-06-09

  The invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.

  本发明涉及一种适用于电子设备的化合物，以及包含该化合物的电子设备，特别是有机电致发光器件。
• MATERIALIEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP3941920A1

  公开（公告）日：2022-01-26
• [EN] MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES<br/>[FR] MATÉRIAUX POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES<br/>[DE] MATERIALIEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN
  申请人：MERCK PATENT GMBH

  公开号：WO2020187865A1

  公开（公告）日：2020-09-24

  Die vorliegende Erfindung betrifft Verbindungen, die sich für die Verwendung in elektronischen Vorrichtungen eignen, sowie elektronische Vorrichtungen, insbesondere organischen Elektrolumineszenzvorrichtungen, enthaltend diese Verbindungen.
• Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls
  作者：Shalini Verma、Manoj Kumar、Pawan K. Mishra、Akhilesh K. Verma

  DOI：10.1021/acs.orglett.9b01649

  日期：2019.7.5

  Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. gamma-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.