2-bromo-3-(3-indolyl)-1,4-naphthoquinone | 1262224-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3-(3-indolyl)-1,4-naphthoquinone
• 英文别名: 2-bromo-3-(1H-indol-3-yl)naphthalene-1,4-dione
• CAS: 1262224-63-4
• 化学式: C₁₈H₁₀BrNO₂
• 分子量: 352.187
• InChiKey: KJHFEWMLKQPTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-碘吲哚 、 2-溴-1,4-萘醌 以 溶剂黄146 为溶剂， 反应 72.0h， 以29%的产率得到2-bromo-3-(3-indolyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Reaction of 3-iodoindole with 1,4-naphthoquinones

  摘要：

  Abstract magnified image The usefulness of 3‐iodoindole available for introduction of an indole unit is presented. The reaction of 3‐iodoindole with 2‐bromo(or methyl)‐1,4‐naphthoquinone in acetic acid gave 2‐bromo(or methyl)‐3‐(3‐indolyl)‐1,4‐naphthoquinone. On the other hand, the reaction of 3‐iodoindole with 2‐bromo‐1,4‐naphthoquinone in the presence of cesium carbonate in acetonitrile produced 2‐(1‐indolyl‐3‐iodo)‐1,4‐naphthoquinone. J. Heterocyclic Chem., (2010).

  DOI：

  10.1002/jhet.492

文献信息

• Reaction of Some Indoles with 1,4-Naphthoquinones in the Presence of Pd(OAc)₂
  作者：Yasuhiro Tanoue、Norihisa Kai、Takeshi Nagai、Mikio Noda

  DOI：10.1002/jhet.2000

  日期：2014.8

  introduction of an indole unit into the 1,4-naphthoquinone skeleton is described. The reaction of the indoles with 1,4-naphthoquinones in CH3CN in the presence of Pd(OAc)2 gave the corresponding 2-(3-indolyl)-1,4-naphthoquinones in moderate yield.

  描述了可用于将吲哚单元引入1，4-萘醌骨架中的反应。在Pd（OAc）2存在下，吲哚与1,4-萘醌在CH 3 CN中的反应以中等收率得到了相应的2-（3-吲哚基）-1,4-萘醌。
• One‐Pot Mechanochemical Synthesis of Mono‐ and Bis‐Indolylquinones via Solvent‐Free Multiple Bond‐Forming Processes
  作者：Marta Piquero、Cristina Font、Natalia Gullón、Pilar López‐Alvarado、J. Carlos Menéndez

  DOI：10.1002/cssc.202101529

  日期：2021.11.4

  with fungi: Bis-indolylquinones are fungal natural products endowed with interesting pharmacological properties. Here a new one-pot mechanochemical methodology for the synthesis of indolylquinones is described, which takes place via domino Michael addition/oxidation processes starting from indoles and dihaloquinones in the presence of FeCl3 or p-TsOH as catalysts and Fetizon's reagent as an oxidant

  有趣的真菌：双吲哚基醌是真菌天然产物，具有有趣的药理特性。这里描述了一种用于合成吲哚基醌的新一锅机械化学方法，该方法通过多米诺迈克尔加成/氧化过程从吲哚和二卤醌开始，在 FeCl 3或p- TsOH 作为催化剂和 Fetizon 试剂作为氧化剂的存在下发生。
• Reaction of 3-iodoindole with 1,4-naphthoquinones
  作者：Yasuhiro Tanoue、Takashi Teraoka、Norihisa Kai、Takeshi Nagai、Kazutoshi Ushio

  DOI：10.1002/jhet.492

  日期：2010.11

  Abstract magnified image The usefulness of 3‐iodoindole available for introduction of an indole unit is presented. The reaction of 3‐iodoindole with 2‐bromo(or methyl)‐1,4‐naphthoquinone in acetic acid gave 2‐bromo(or methyl)‐3‐(3‐indolyl)‐1,4‐naphthoquinone. On the other hand, the reaction of 3‐iodoindole with 2‐bromo‐1,4‐naphthoquinone in the presence of cesium carbonate in acetonitrile produced 2‐(1‐indolyl‐3‐iodo)‐1,4‐naphthoquinone. J. Heterocyclic Chem., (2010).