2,2-dichlorovinyl-4'-methylacetophenone | 926890-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dichlorovinyl-4'-methylacetophenone
• 英文别名: 4,4-dichloro-1-(4-tolyl)but-3-en-1-one；4,4-Dichloro-1-(4-methylphenyl)but-3-en-1-one
• CAS: 926890-67-7
• 化学式: C₁₁H₁₀Cl₂O
• 分子量: 229.106
• InChiKey: PALURMCUCWBMDO-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C(Solv: ligroine (8032-32-4))
• 沸点：
  352.9±42.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2,2-dichlorovinyl-4'-methylacetophenone 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以45%的产率得到4,4-dichloro-1-(4-tolyl)but-2-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
• 作为产物：
  描述：

  p-Tolyl-3,3,3-trichlor-prop-1-enyl-keton 生成 2,2-dichlorovinyl-4'-methylacetophenone
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.05.084

文献信息

• 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.