3-mesityl-4-(3-hydroxyphenyl)-5-phenyl-4,5-dihydroisoxazole

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-mesityl-4-(3-hydroxyphenyl)-5-phenyl-4,5-dihydroisoxazole
• 英文别名: 3-[(4S,5S)-5-phenyl-3-(2,4,6-trimethylphenyl)-4,5-dihydro-1,2-oxazol-4-yl]phenol
• 化学式: C₂₄H₂₃NO₂
• 分子量: 357.452
• InChiKey: GPOFFPRGDICORS-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间羟基苯甲醛 在 hydroxide 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 3-mesityl-4-(3-hydroxyphenyl)-5-phenyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Cycloadditions of Mesitonitrile Oxide with Hydroxy- and Methoxy-substituted Stilbenes. A Directing Hydrogen Bonding Model

  摘要：

  The regioselectivity of the reaction of mesitonitrile oxide with o-hydroxystilbene in favour of the 5-(2-hydroxyphenyl) isomer (regioisomeric ratio 5:1) is accounted by a directing hydrogen bonding model, while for reactions of the p-hydroxy- and p-methoxystilbene which show a 2:1 ratio between the 5- and 4-regioisomer, an electron-donor effect is invoked. These phenomena of regioselectivity are supported by semiempirical AM1 calculations.

  DOI：

  10.3987/com-97-8099

文献信息

• Cycloadditions of Mesitonitrile Oxide with Hydroxy- and Methoxy-substituted Stilbenes. A Directing Hydrogen Bonding Model
  作者：Antonino Corsaro、Giuseppe Buemi、Ugo Chiacchio、Venerando Pistarà、Antonio Rescifina

  DOI：10.3987/com-97-8099

  日期：——

  The regioselectivity of the reaction of mesitonitrile oxide with o-hydroxystilbene in favour of the 5-(2-hydroxyphenyl) isomer (regioisomeric ratio 5:1) is accounted by a directing hydrogen bonding model, while for reactions of the p-hydroxy- and p-methoxystilbene which show a 2:1 ratio between the 5- and 4-regioisomer, an electron-donor effect is invoked. These phenomena of regioselectivity are supported by semiempirical AM1 calculations.