3-(1H-indol-3-yl)cyclopent-2-en-1-one | 1227178-00-8

• 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: 3-(1H-indol-3-yl)cyclopent-2-en-1-one
• 英文别名: 3-(1H-indol-3-yl)cyclopent-2-enone
• CAS: 1227178-00-8
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: GXEHNDTWEBUKOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1H-indol-3-yl)cyclopent-2-en-1-one 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 二氯甲烷 为溶剂， 反应 72.0h， 以23%的产率得到4-(2-(1H-indol-3-yl)-5-oxocyclopent-1-enyl)-5-chloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
  参考文献：
  名称：

  New 3-vinylation products of indole and investigation of its Diels–Alder reactivity: synthesis of unusual Morita–Baylis–Hillman-type products

  摘要：

  3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.081
• 作为产物：
  描述：

  3-(1H-indol-3-yl)cyclopentanone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.5h， 以28%的产率得到3-(1H-indol-3-yl)cyclopent-2-en-1-one
  参考文献：
  名称：

  New 3-vinylation products of indole and investigation of its Diels–Alder reactivity: synthesis of unusual Morita–Baylis–Hillman-type products

  摘要：

  3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.081

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。
• New 3-vinylation products of indole and investigation of its Diels–Alder reactivity: synthesis of unusual Morita–Baylis–Hillman-type products
  作者：Ali Enis Sadak、Tayfun Arslan、Neslihan Celebioglu、Nurullah Saracoglu

  DOI：10.1016/j.tet.2010.02.081

  日期：2010.4

  3-Vinylindoles as precursors of carbazole and bis-indole derivatives were synthesized. Then, to form new carbazoles, Diels-Alder reactivity of these vinylindoles was studied with various dienophiles. During the cycloaddition reaction, unusual Morita-Baylis-Hillman-type products were observed. The structure and the formation mechanism of the products is discussed. (C) 2010 Elsevier Ltd. All rights reserved.