4-苯基-4-(2-苯基-1H-吲哚-3-基)丁烷-2-酮 | 729580-76-1

• 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
• 中文名称: 4-苯基-4-(2-苯基-1H-吲哚-3-基)丁烷-2-酮
• 英文名称: 4-phenyl-4-(2-phenyl-1H-indol-3-yl)butan-2-one
• 英文别名: 2-Butanone, 4-phenyl-4-(2-phenyl-1H-indol-3-yl)-
• CAS: 729580-76-1
• 化学式: C₂₄H₂₁NO
• 分子量: 339.437
• InChiKey: GACNCPIGRJZYJS-UHFFFAOYSA-N

物化性质

• 沸点：
  546.9±38.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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-苯基乙炔基胺 、 苄叉丙酮 在 palladium dichloride 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以75%的产率得到4-苯基-4-(2-苯基-1H-吲哚-3-基)丁烷-2-酮
  参考文献：
  名称：

  The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

  摘要：

  A cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2 provided 2,3-disubstituted indole derivatives, whereas, in the presence of Pd(OAc)(2), the same reaction resulted in the production of N-alkylated-2-alkynylaniline derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.081

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。
• Samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins
  作者：Zhuang-Ping Zhan、Rui-Feng Yang、Kai Lang

  DOI：10.1016/j.tetlet.2005.03.174

  日期：2005.5

  The SmI3-catalyzed reaction of indoles with electron-deficient olefins generated the corresponding Michael adducts in high yields. The substitution on the indole nucleus occurred exclusively at the 3-position and N-alkylation products have not been observed.

  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。
• 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.