(E)-1-(3-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one

• 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
• 英文名称: (E)-1-(3-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one
• 英文别名: (E)-1-(3-hydroxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one；1-(3-hydroxy-phenyl)-3-(2-nitro-phenyl)-propenone
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: INFDRUVVQFRLNU-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基苯乙酮 、 邻硝基苯甲醛 在 silica gel supported KHSO₄ 作用下， 92.0~99.0 ℃ 、570.01 kPa 条件下， 反应 0.1h， 以81%的产率得到(E)-1-(3-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one
  参考文献：
  名称：

  Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen–Schmidt condensation

  摘要：

  The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO4-SiO2 as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.106

文献信息

• Visible Light Activated Radical Denitrative Benzoylation of<i>β</i>-Nitrostyrenes: A Photocatalytic Approach to Chalcones
  作者：Shubhangi Tripathi、Ritu Kapoor、Lal Dhar S. Yadav

  DOI：10.1002/adsc.201701559

  日期：2018.4.3

  A metal‐free, convenient photocatalytic approach to chalcones from β‐nitrostyrenes and benzaldehydes via a radical denitrative benzoylation pathway is reported. The salient features of the protocol include the utilization of visible light as an inexpensive and ecosustainable energy source, N‐hydroxyphthalimide (NHPI) as a reusable organophotocatalyst and acetonitrile as an acceptable green solvent

  据报道，一种无金属，方便的光催化方法可通过自由基反硝化苯甲酰化途径从β-硝基苯乙烯和苯甲醛中分离出查耳酮。该协议的显着特征包括利用可见光作为一种廉价且生态可持续的能源，使用N-羟基邻苯二甲酰亚胺（NHPI）作为可重复使用的有机光催化剂，使用乙腈作为一种可接受的绿色溶剂，以在室温下以优异的产率提供查耳酮。锅程序。值得注意的是，这是β-硝基苯乙烯作为查尔酮合成的现成底物的首次应用，也是该领域中光催化的第一个实例。
• A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate
  作者：T. Narender、K. Papi Reddy

  DOI：10.1016/j.tetlet.2007.03.054

  日期：2007.4

  Chalcones are secondary metabolites of terrestrial plants, precursors for the biosynthesis of ilavonoids and exhibit various biological activities. Condensation of substituted acetophenones (2a-12a) with various aromatic aldehydes (1b-7b) in the presence of BF3-Et2O at room temperature gave chalcones in 75-96% yield. (c) 2007 Published by Elsevier Ltd.