5-dichloromethyl-3-(4'-methylphenyl)-2-isoxazoline | 1320360-76-6

• 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: 5-dichloromethyl-3-(4'-methylphenyl)-2-isoxazoline
• 英文别名: 5-(Dichloromethyl)-3-(4-methylphenyl)-4,5-dihydro-1,2-oxazole；5-(dichloromethyl)-3-(4-methylphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 1320360-76-6
• 化学式: C₁₁H₁₁Cl₂NO
• 分子量: 244.12
• InChiKey: YEVRXECIUQYOEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-dichlorovinyl-4'-methylacetophenone 在 羟胺 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 5-dichloromethyl-3-(4'-methylphenyl)-2-isoxazoline
  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 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.