3-(3-methyl-1H-indol-2-yl)cyclohexanone

• 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: 3-(3-methyl-1H-indol-2-yl)cyclohexanone
• 英文别名: 3-(3-methyl-2-indolyl)cyclohexan-1-one；3-(3-methyl-1H-indol-2-yl)cyclohexan-1-one
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: AMQPDLMPTZZOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基吲哚 、 2-环己烯-1-酮 在 sodium tetrachloroaurate(III) 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以75%的产率得到3-(3-methyl-1H-indol-2-yl)cyclohexanone
  参考文献：
  名称：

  吲哚与α,β-烯酮的金催化共轭加成反应

  摘要：

  3-未取代的吲哚通过金催化的与α,β-烯酮的共轭加成反应在吲哚核的3-位发生区域选择性烷基化。3-取代的吲哚经历 C-2 烷基化。用二亚苄基丙酮对吲哚进行连续的 C-3/C-2 金催化烷基化得到多环吲哚 b 环，并具有七元环。

  DOI：

  10.1055/s-2004-822903

文献信息

• Bismuth Nitrate-Catalyzed Versatile Michael Reactions
  作者：Neeta Srivastava、Bimal K. Banik

  DOI：10.1021/jo026550s

  日期：2003.3.1

  Bismuth nitrate-catalyzed versatile Michael reaction was developed to reduce the complications that characterize the current standard Michael reaction and used for facile preparation of organic compounds of widely different structures. For example, several substituted amines, imidazoles, thio compounds, indoles, and carbamates were prepared at room temperature by following this method. In contrast

  硝酸铋催化的通用迈克尔反应的开发是为了减少目前标准迈克尔反应所特有的复杂性，并用于方便地制备结构迥异的有机化合物。例如，按照该方法在室温下制备几种取代的胺，咪唑，硫代化合物，吲哚和氨基甲酸酯。与使用许多酸性催化剂的现有方法相比，该方法非常通用，简单，高产率，环境友好并且耐氧气和湿气。但是，目前尚不了解硝酸铋在该反应中的促进作用。
• Gold-Catalyzed Conjugate Addition Type Reaction of Indoles with α,β-Enones
  作者：Antonio Arcadi、Gabriele Bianchi、Marco Chiarini、Gaetano D’Anniballe、Fabio Marinelli

  DOI：10.1055/s-2004-822903

  日期：——

  3-Unsubstituted indoles undergo regioselective alkylation at the 3-position of the indole nucleus through gold-catalyzed conjugated addition type reaction with α,β-enones. 3-Substituted indoles undergo C-2 alkylation. Sequential C-3/C-2 gold catalyzed alkylation of the indole with dibenzylidene acetone gives a polycyclic indole b-annulated with a seven-membered cycle.

  3-未取代的吲哚通过金催化的与α,β-烯酮的共轭加成反应在吲哚核的3-位发生区域选择性烷基化。3-取代的吲哚经历 C-2 烷基化。用二亚苄基丙酮对吲哚进行连续的 C-3/C-2 金催化烷基化得到多环吲哚 b 环，并具有七元环。
• Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition
  作者：Bimal K. Banik、Miguel Fernandez、Clarissa Alvarez

  DOI：10.1016/j.tetlet.2005.02.044

  日期：2005.4

  Michael reaction of indoles with unsaturated ketones has been accomplished in the presence of catalytic amount of iodine under solvent-free condition. (c) 2005 Published by Elsevier Ltd.
• Bismuth Nitrate-Catalyzed Michael Reactions of Indoles in Water
  作者：Bimal K. Banik、Isabella Garcia、Frances R. Morales

  DOI：10.3987/com-06-10957

  日期：——
• Regioselective N- and C2-electrophilic substitution of 3-substituted indoles
  作者：Sarah Leitch、Jennifer Addison-Jones、Adam McCluskey

  DOI：10.1016/j.tetlet.2005.02.153

  日期：2005.4

  The reaction of 3-substituted indoles with 2-cyclohexenone under Lewis acid mediated conditions with Bi(NO3)(3)-5H(2)O has been investigated. We have demonstrated that electrophilic substitution of 3-substituted indoles with 2-cyclohexenone will readily occur at the nitrogen. Furthermore, the extent of regioselectivity is dependent on reaction solvent and the C3-substituent. Excellent conversion is obtained with good to excellent isolated yields of N- and C2-adducts. In general, more polar, aprotic solvents (CH3CN) give greater N-selectivity whereas with polar protic solvents (CH3OH) an increase in the C2-adduct is observed. (c) 2005 Elsevier Ltd. All rights reserved.