4,4,4-trichloro-1-(4-phenylphenyl)but-2-en-1-one | 1184912-94-4

• 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: 4,4,4-trichloro-1-(4-phenylphenyl)but-2-en-1-one
• CAS: 1184912-94-4
• 化学式: C₁₆H₁₁Cl₃O
• 分子量: 325.622
• InChiKey: PYHXHQXNIQJONM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,4,4-trichloro-1-(4-phenylphenyl)but-2-en-1-one 在 羟胺 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 2,2-dichlorovinyl-4'-phenylacetophenone oxime
  参考文献：
  名称：

  A new and efficient approach to isoxazolines. First synthesis of 3-aryl-5-dichloromethyl-2-isoxazolines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.05.110

文献信息

• 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。
• 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.