3-(2-phenyl-1H-indol-3-yl)cyclohexanone | 729580-77-2

• 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-(2-phenyl-1H-indol-3-yl)cyclohexanone
• 英文别名: Cyclohexanone, 3-(2-phenyl-1H-indol-3-yl)-；3-(2-phenyl-1H-indol-3-yl)cyclohexan-1-one
• CAS: 729580-77-2
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: DPZPMTRHEVAEBW-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-环己烯-1-酮 、 2-苯基吲哚 在 samarium (III) iodide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以90%的产率得到3-(2-phenyl-1H-indol-3-yl)cyclohexanone
  参考文献：
  名称：

  io三碘化物催化的吲哚与缺电子烯烃的共轭加成反应

  摘要：

  吲哚与SmI 3催化的缺电子烯烃反应以高收率生成了相应的迈克尔加合物。吲哚核上的取代仅发生在3-位，并且未观察到N-烷基化产物。

  DOI：

  10.1016/j.tetlet.2005.03.174

文献信息

• 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。
• Microwave-Accelerated Samarium Triiodide Catalyzed Conjugate Addition of Indoles with Electron-Deficient Olefins
  作者：Zhuang-Ping Zhan、Kai Lang

  DOI：10.1055/s-2005-869849

  日期：——

  A fast, efficient, environmentally benign, solvent-free procedure under microwave irradiation, using silica gel supported reagents, for the samarium triiodide catalyzed conjugated addition of indoles with electron-deficient olefins has been developed.

  已经开发了一种在微波辐射下使用硅胶支持的试剂快速、高效、环境友好、无溶剂的程序，用于三碘化钐催化吲哚与缺电子烯烃的共轭加成。
• Gold-Catalyzed Reactions of 2-Alkynyl-phenylamines with α,β-Enones
  作者：Maria Alfonsi、Antonio Arcadi、Massimiliano Aschi、Gabriele Bianchi、Fabio Marinelli

  DOI：10.1021/jo047793i

  日期：2005.3.1

  The gold-catalyzed reaction of 2-alkynyl-phenylamines with alpha,beta-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/alpha,beta-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 degrees C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.
• Lewis Acid Catalysis with Cationic Dinuclear Gold(II,II) and Gold(III,III) Phosphorus Ylide Complexes
  作者：Benjamin R. Reiner、Mark W. Bezpalko、Bruce M. Foxman、Casey R. Wade

  DOI：10.1021/acs.organomet.6b00403

  日期：2016.9.12

  The.dinuclear gold(II,II) and gold(III,III) complexes [Au-2(mu-PY)(2)(MeCN)(2)]OTf2 (2-OTf2) and [Au-2(mu-PY)(2)(mu-CH2)(MeCN)(2)]OTf2 (3-OTf2) (PY = [(CH2)(2)PPh2](-)) have been synthesized and evaluated as Lewis acid catalysts for Mukaiyama addition and alkyne hydroamination reactions. 2-OTf2 and 3-OTf2 provide similar or improved catalytic activity for these reactions compared to the commonly used gold(I) Lewis acids Ph3PAuOTf and IPrAuOTf. The versatile Lewis acidity of 2-OTf2 was further demonstrated by its superior performance in a cascade reaction involving intramolecular hydroamination followed by intermolecular conjugate addition to generate a 2,3-substituted indole.