4,4-dichloro-1-(4-chlorophenyl)but-3-en-1-one | 807331-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-dichloro-1-(4-chlorophenyl)but-3-en-1-one
• 英文别名: 2,2-dichlorovinyl-4'-chloroacetophenone
• CAS: 807331-46-0
• 化学式: C₁₀H₇Cl₃O
• 分子量: 249.524
• InChiKey: XIWSHQVXOAQODM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  3
• 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：

  4,4-dichloro-1-(4-chlorophenyl)but-3-en-1-one 在 肼 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以93%的产率得到5-dichloromethyl-3-(4-chlorophenyl)-2-pyrazoline
  参考文献：
  名称：

  3-芳基-5-二氯甲基-2-吡唑啉的首次合成。电化学生成2，2-二氯乙烯基苯乙酮是关键步骤

  摘要：

  已经建立了标题化合物的有效合成途径。Chloralacetophenones 2被治疗的苯乙酮的制备1用无水三氯乙醛。中间体的脱水2的酸性条件下得到2,2,2- trichloroethylideneacetophenones 3，将其转化为2,2- dichlorovinylacetophenones 5中任一处或汞石墨电极几乎定量的产率通过选择性电化学monodechlorination。最后，用肼或甲基肼处理化合物5可有效地获得3-芳基-5-二氯甲基-2-吡唑啉7。

  DOI：

  10.1016/j.tetlet.2004.09.101
• 作为产物：
  描述：

  4,4,4-trichloro-1-(4-chlorophenyl)-3-hydroxybutan-1-one 在 硫酸 、 lithium perchlorate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 4,4-dichloro-1-(4-chlorophenyl)but-3-en-1-one
  参考文献：
  名称：

  1-芳基-4,4-二氯丁-3-烯-1-酮的首次合成。1-芳基-4,4,4-三氯丁-2-烯-1-酮的电化学还原是关键步骤

  摘要：

  报道了合成1-芳基-4，4-二氯丁-3-烯-1-酮的第一种方法。用无水氯醛处理苯乙酮可得到接近定量产率的1-芳基-4,4,4-三氯-3-羟基丁-1-酮。用硫酸或对甲苯磺酸将这些化合物有效脱水，得到1-芳基-4,4,4-三氯丁-2-烯-1-酮，通过电化学将其选择性转化为标题化合物，以公平至定量的收率减少。已经确定了4，4-二氯-1-（4-甲氧基苯基）but-3-en-1-one的X射线晶体结构。借助于HF和B3LYP密度泛函理论方法，讨论了β，γ-不饱和酮的优先形成以及相应的α，β-不饱和异构体的完全排除。

  DOI：

  10.1016/j.tet.2006.11.054

文献信息

• First synthesis of 3-aryl-5-dichloromethyl-2-pyrazolines. The electrochemical generation of 2,2-dichlorovinylacetophenones as a key step
  作者：Antonio Guirado、Bruno Martiz、Raquel Andreu

  DOI：10.1016/j.tetlet.2004.09.101

  日期：2004.11

  intermediates 2 under acidic conditions yielded 2,2,2-trichloroethylideneacetophenones 3, which were transformed to 2,2-dichlorovinylacetophenones 5 in nearly quantitative yields by selective electrochemical monodechlorination at either mercury or graphite electrodes. Finally, 3-aryl-5-dichloromethyl-2-pyrazolines 7 were efficiently obtained on treatment of compounds 5 with either hydrazine or methylhydrazine

  已经建立了标题化合物的有效合成途径。Chloralacetophenones 2被治疗的苯乙酮的制备1用无水三氯乙醛。中间体的脱水2的酸性条件下得到2,2,2- trichloroethylideneacetophenones 3，将其转化为2,2- dichlorovinylacetophenones 5中任一处或汞石墨电极几乎定量的产率通过选择性电化学monodechlorination。最后，用肼或甲基肼处理化合物5可有效地获得3-芳基-5-二氯甲基-2-吡唑啉7。
• 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.
• First synthesis of 1-aryl-4,4-dichlorobut-3-en-1-ones. The electrochemical reduction of 1-aryl-4,4,4-trichlorobut-2-en-1-ones as a key step
  作者：Antonio Guirado、Bruno Martiz、Raquel Andreu、Delia Bautista、Jesús Gálvez

  DOI：10.1016/j.tet.2006.11.054

  日期：2007.1

  The first method for the synthesis of 1-aryl-4,4-dichlorobut-3-en-1-ones is reported. Treatment of acetophenones with anhydrous chloral leads to 1-aryl-4,4,4-trichloro-3-hydroxybutan-1-ones in near quantitative yields. These compounds were efficiently dehydrated with either sulfuric or p-toluenesulfonic acid to give 1-aryl-4,4,4-trichlorobut-2-en-1-ones, which were selectively converted to the title

  报道了合成1-芳基-4，4-二氯丁-3-烯-1-酮的第一种方法。用无水氯醛处理苯乙酮可得到接近定量产率的1-芳基-4,4,4-三氯-3-羟基丁-1-酮。用硫酸或对甲苯磺酸将这些化合物有效脱水，得到1-芳基-4,4,4-三氯丁-2-烯-1-酮，通过电化学将其选择性转化为标题化合物，以公平至定量的收率减少。已经确定了4，4-二氯-1-（4-甲氧基苯基）but-3-en-1-one的X射线晶体结构。借助于HF和B3LYP密度泛函理论方法，讨论了β，γ-不饱和酮的优先形成以及相应的α，β-不饱和异构体的完全排除。
• 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.