3-(5-methoxy-1H-indol-3-yl)cyclohex-2-en-1-one

• 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-(5-methoxy-1H-indol-3-yl)cyclohex-2-en-1-one
• 英文别名: 3-(5-methoxy-1H-indol-3-yl)-cyclohex-2-enone
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: JUJCRWOLEVFDHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 1,3-环己二酮 在 三氯化铁 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以86%的产率得到3-(5-methoxy-1H-indol-3-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  FeCl3-catalyzed alkylation of indoles with 1,3-dicarbonyl compounds: an expedient synthesis of 3-substituted indoles

  摘要：

  Indoles undergo smooth alkylation at the 3-position with 1,3-dicarbonyl compounds in the presence of 20 mol % of FeCl3 under mild reaction conditions to produce a wide range of 3-substituted indoles in excellent yields and with high E-selectivity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.166

文献信息

• Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications
  作者：Zhen-Kang Wen、Xiao-Xue Wu、Wen-Kai Bao、Jing-Jing Xiao、Jian-Bin Chao

  DOI：10.1021/acs.orglett.0c01763

  日期：2020.6.19

  Herein, we report a palladium-catalyzed dehydrogenative cross-coupling of indoles with cyclic enones to give β-indolyl cyclic enones under mild and neutral reaction conditions. The key to the success is to explore a mild condition, which ensures the indole C–H activation and subsequent syn β-hydride elimination through rapid enolization isomerization of Pd(II)-enolate while suppressing other undesired

  本文中，我们报道了在温和和中性反应条件下，钯催化的吲哚与环烯酮的脱氢交叉偶联，从而得到β-吲哚基环状的烯酮。成功的关键是探索一种温和的条件，该条件可确保Pd（II）-烯酸酯的快速烯化异构化，同时抑制其他不希望的副反应，从而确保吲哚C–H活化和随后的顺式β-氢化物消除。在偶联产物向间苯酚和苯并[a]咔唑的柔性转化中也证明了合成用途。
• Task-specific ionic liquid-catalyzed efficient couplings of indoles with 1,3-dicarbonyl compounds: an efficient synthesis of 3-alkenylated indoles
  作者：Sougata Santra、Adinath Majee、Alakananda Hajra

  DOI：10.1016/j.tetlet.2011.05.069

  日期：2011.7

  Direct alkenylation of indoles at the 3-position with 1,3-dicarbonyl compounds under Bronsted acidic ionic liquid catalysis has been developed. The yields were excellent, and the catalyst can be reused at least six times without noticeable loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.