1,3-二苯基-3-(2-苯基-1H-吲哚-3-基)丙烷-1-酮 | 557785-79-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3-二苯基-3-(2-苯基-1H-吲哚-3-基)丙烷-1-酮
• 英文名称: 1,3-diphenyl-3-(2-phenyl-1H-indol-3-yl)propan-1-one
• CAS: 557785-79-2
• 化学式: C₂₉H₂₃NO
• 分子量: 401.508
• InChiKey: FCTSEHSPSISHKE-UHFFFAOYSA-N

物化性质

• 沸点：
  646.4±55.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1,3-二苯基-3-(2-苯基-1H-吲哚-3-基)丙烷-1-酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到1,3-diphenyl-3-(2-phenyl-3-indolyl)-1-propanol
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1021725312271
• 作为产物：
  描述：

  2-苯基乙炔基胺 、 反式-查耳酮 在 sodium tetrachloroaurate(III) 作用下， 以 乙醇 为溶剂， 反应 9.0h， 以82%的产率得到1,3-二苯基-3-(2-苯基-1H-吲哚-3-基)丙烷-1-酮
  参考文献：
  名称：

  Gold-Catalyzed Reactions of 2-Alkynyl-phenylamines with α,β-Enones

  摘要：

  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.

  DOI：

  10.1021/jo047793i

文献信息

• Fluorinated Alcohol-Mediated S_N1-Type Reaction of Indolyl Alcohols with Diverse Nucleophiles
  作者：Hao Wen、Liang Wang、Lubin Xu、Zhihui Hao、Chang-Lun Shao、Chang-Yun Wang、Jian Xiao

  DOI：10.1002/adsc.201500500

  日期：2015.12.14

  This paper describes an efficient SN1-type reaction of 3-indolylmethanols with miscellaneous nucleophiles, featuring a catalyst-free procedure, low cost, wide substrate scope and mild reaction conditions. This approach provides green and efficient methods for the synthesis of diverse 3-substituted indolyl derivatives as well as unsymmetrical bisindolylmethanes and triarylmethanes.

  本文介绍了3-吲哚甲醇与杂种亲核试剂的高效S N 1型反应，具有无催化剂操作，成本低，底物范围宽和反应条件温和的特点。这种方法为合成各种3-取代的吲哚基衍生物以及不对称的双吲哚基甲烷和三芳基甲烷提供了绿色有效的方法。
• Catalyst-free dehydrative S_N1-type reaction of indolyl alcohols with diverse nucleophiles “on water”
  作者：Jian Xiao、Hao Wen、Liang Wang、Lubin Xu、Zhihui Hao、Chang-Lun Shao、Chang-Yun Wang

  DOI：10.1039/c5gc01838b

  日期：——

  An efficient dehydrative S_N1-type reaction of indolyl alcohols with diverse nucleophiles was developed using water as the solvent, affording versatile 3-indolyl derivatives in high yields. The advantages of being catalyst-free, environmentally benign, and wide substrate scope make it a promising method for preparation of indolyl compounds.

  利用水作为溶剂，开发了一种高效的无催化剂的脱水性SN1型反应，可将吲哚醇与多样的亲核试剂反应，产率高，得到多功能的3-吲哚衍生物。无需催化剂、环境友好且底物范围广泛的优点使其成为制备吲哚化合物的一种有前景的方法。
• Metal-Free Dehydrogenative Double C–H Sulfuration To Access Thieno[2,3-<i>b</i>]indoles Using Elemental Sulfur
  作者：Jianming Liu、Yanyan Zhang、Yuanyuan Yue、Zhixian Wang、Huibin Shao、Kelei Zhuo、Qingzhang Lv、Zhiguo Zhang

  DOI：10.1021/acs.joc.9b01586

  日期：2019.10.18

  synthesis of thieno[2,3-b]indole derivatives. This method combined four C-H σ-bond cleavage reactions of two different kinds of C-H bonds and two C-S σ-bond formation processes. A series of thieno[2,3-b]indoles were obtained starting from 3-benzylindole derivatives with good yields and high regioselectivity, with the elemental sulfur serving as a cheap and readily available sulfur source. Good efficiency

  我们报告了碱促进的无金属合成噻吩并[2,3-b]吲哚衍生物的方法。该方法结合了两种不同CH键的四个CHσ键断裂反应和两个CSσ键形成过程。从3-苄基吲哚衍生物以良好的收率和高的区域选择性获得了一系列的噻吩并[2，3-b]吲哚，元素硫是一种廉价且容易获得的硫源。即使以克为单位进行反应，也可以保持良好的效率。在机理研究的基础上提出了一个合理的机制。
• Al(OTf)3 Catalysed Friedel-Crafts Michael Type Addition of Indoles to α,β-Unsaturated Ketones with PEG-200 as Recyclable Solvent
  作者：Mukut Gohain、Jc Jacobs、Charlene Marais、Barend C. B. Bezuidenhoudt

  DOI：10.1071/ch13254

  日期：——

  An Al(OTf)3 catalysed efficient Friedel–Crafts Michael type addition of indoles to α,β-unsaturated ketones using recyclable PEG-200 as an alternative reaction solvent is disclosed. The reaction under microwave irradiation is clean, leads to excellent yields in minutes and reduces the use of volatile organic compounds.

  公开了使用可回收的PEG-200作为替代反应溶剂的Al（OTf）3催化的吲哚向α，β-不饱和酮的高效Friedel-Crafts Michael型加成反应。微波辐射下的反应是干净的，可在数分钟内获得优异的收率，并减少了挥发性有机化合物的使用。
• The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles
  作者：Donala Janreddy、Veerababurao Kavala、Chun-Wei Kuo、Ting-Shen Kuo、Chiu-Hui He、Ching-Fa Yao

  DOI：10.1016/j.tet.2013.01.081

  日期：2013.4

  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.