p-Bromphenyl-3,3,3-trichlor-prop-1-enyl-keton | 73498-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-Bromphenyl-3,3,3-trichlor-prop-1-enyl-keton
• 英文别名: 1-(4-Bromophenyl)-4,4,4-trichlorobut-2-en-1-one
• CAS: 73498-41-6
• 化学式: C₁₀H₆BrCl₃O
• 分子量: 328.42
• InChiKey: FRTIDAJCXLPVRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-Bromphenyl-3,3,3-trichlor-prop-1-enyl-keton 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 以56%的产率得到3-(p-Bromphenyl)-5-trichlormethyl-Δ²-isoxazolin
  参考文献：
  名称：

  Voigt, Helga, Zeitschrift fur Chemie, 1980, vol. 20, # 1, p. 19

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(4-bromophenyl)-4,4,4-trichloro-3-hydroxybutan-1-one 在 硫酸 作用下， 生成 p-Bromphenyl-3,3,3-trichlor-prop-1-enyl-keton
  参考文献：
  名称：

  Voigt,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1978, vol. 320, p. 933 - 936

  摘要：

  DOI：

文献信息

• A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones
  作者：Antonio Guirado、Enrique Alarcón、Yesica Vicente、Raquel Andreu

  DOI：10.1016/j.tetlet.2013.07.075

  日期：2013.9

  2-Trichloroethylideneacetophenones reacted with benzamidines leading to novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. These compounds were efficiently dehydrated to obtain previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines, which were able to undergo aromatisation via chloroform elimination to give 2,4-diarylpyrimidines in high

  已经开发了一种有利的2，4-二芳基嘧啶的新方法。2,2,2-三氯亚乙基苯乙酮与苄am反应，以接近定量的产率得到新型的2,6-二芳基-6-羟基-4-三氯甲基-1,4,5,6-四氢嘧啶。这些化合物被有效地脱水以获得先前未知的2,4-二芳基-6-三氯甲基-1,6-二氢嘧啶，这些化合物能够通过氯仿消除进行芳构化，从而以高收率得到2,4-二芳基嘧啶。该方法的主要改进在于避免了二氢嘧啶中间体的氧化脱氢。该制备过程也已经适应于一锅法方案。
• A new convenient synthetic approach to diarylpyrimidines
  作者：Antonio Guirado、Enrique Alarcón、Yesica Vicente、Raquel Andreu、Delia Bautista、Jesús Gálvez

  DOI：10.1016/j.tet.2016.05.018

  日期：2016.7

  A new synthetic method in pyrimidine chemistry has been developed. 2,2,2-Trichloroethylideneacetophenones, easily available from chloral and acetophenones, reacted with benzamidines to provide novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. Efficient dehydration of these compounds gave previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines

  已开发出嘧啶化学的一种新的合成方法。2,2,2-三氯亚乙基苯乙酮，很容易从氯醛和苯乙酮中获得，与苯甲idine反应，以接近定量的产率提供新的2,6-二芳基-6-羟基-4-三氯甲基-1,4,5,6-四氢嘧啶。这些化合物的有效脱水产生了以前未知的2,4-二芳基-6-三氯甲基-1,6-二氢嘧啶，发现它们能够进行碱诱导的氯仿消除，从而以高收率得到2,4-二芳基嘧啶。通过单晶X射线衍射确定最终和中间化合物的分子结构。该方法的主要改进在于通过氯仿消除工艺来规避二氢嘧啶中间体的氧化芳构化。
• Highly enantioselective yttrium(iii)-catalyzed Friedel–Crafts alkylation of β-trichloro(trifluoro)methyl aryl enones with indoles
  作者：Wentao Wang、Xiangjin Lian、Donghui Chen、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1039/c1cc12306h

  日期：——

  An efficient yttrium(III)-catalyzed highly enantioselective Friedel-Crafts alkylation of beta-trichloro(trifluoro)methyl aryl enones is described. The reaction delivered a series of functionalized indoles with a chiral tertiary carbon center bearing a trichloro(trifluoro)methyl group in excellent results (up to 96% ee and 99% yield) under mild conditions.

  描述了有效的钇（III）催化的β-三氯（三氟）甲基芳基烯酮的高度对映选择性的弗瑞德-克来福特烷基化。该反应在温和的条件下以优异的结果（高达96％ee和99％收率）提供了一系列带有手性叔碳中心的带有三氯（三氟）甲基的官能化吲哚。
• A new and efficient approach to pyrazolines. First synthesis of 3-aryl-5-dichloromethyl-2-pyrazolines
  作者：Antonio Guirado、Bruno Martiz、Raquel Andreu、Delia Bautista

  DOI：10.1016/j.tet.2009.05.084

  日期：2009.8

  An efficient synthetic method for dichloromethylated pyrazolines has been established. 1-Aryl-4,4-dichlorobut-3-en-1-ones 4 were efficiently prepared by treatment of acetophenones with anhydrous chloral, followed by dehydration and reductive dechlorination. Compounds 4 reacted with hydrazine hydrate and methylhydrazine to give the respective 5-dichloromethyl-2-pyrazolines in high to quantitative yields. The molecular structure of 5-dichoromethyl-1-methyl-3-(2-naphthyl)-2-pyrazoline has been determined by X-ray crystallography. (C) 2009 Elsevier Ltd. All rights reserved.
• A new and efficient approach to isoxazolines. First synthesis of 3-aryl-5-dichloromethyl-2-isoxazolines
  作者：Antonio Guirado、Bruno Martiz、Raquel Andreu、Delia Bautista

  DOI：10.1016/j.tet.2011.05.110

  日期：2011.8

  An efficient synthetic method for 3-aryl-5-dichloromethyl-2-isoxazolines has been established. Reactions between anhydrous chloral and acetophenones in hot acetic acid lead to 1-aryl-4,4,4-trichloro-3-hydroxybutan-1-ones (chloralacetophenones), which provided 1-aryl-4,4-dichlorobut-3-en-1-ones (2,2-dichlorovinylacetophenones) by dehydration and subsequent electrochemical reduction. These beta,gamma-unsaturated enones reacted with hydroxylamine yielding oxime intermediates whose treatment with aqueous sodium hydroxide gave novel 3-aryl-5-dichloromethyl-2-isoxazolines in fair to high yields. The molecular structure of a member of this family of compounds, 5-dichoromethyl-3-(4-methoxyphenyl)-2-isoxazoline, was determined by X-ray crystallography. (C) 2011 Elsevier Ltd. All rights reserved.