3-(4-Bromo-benzyl)-6-(4-bromo-phenyl)-3,5,5-trimethyl-dihydro-pyran-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(4-Bromo-benzyl)-6-(4-bromo-phenyl)-3,5,5-trimethyl-dihydro-pyran-2,4-dione
• 英文别名: 3-(4-bromobenzyl)-6-(4-bromophenyl)-3,5,5-trimethyldihydro-2H-pyran-2,4(3H)-dione；6-(4-bromophenyl)-3-[(4-bromophenyl)methyl]-3,5,5-trimethyloxane-2,4-dione
• 化学式: C₂₁H₂₀Br₂O₃
• 分子量: 480.196
• InChiKey: MIQOXYZDVDPVMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对硝基溴化苄 、 sodium;2-(4-bromophenyl)-3,3,5-trimethyl-6-oxo-2H-pyran-4-olate 在 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 3-(4-Bromo-benzyl)-6-(4-bromo-phenyl)-3,5,5-trimethyl-dihydro-pyran-2,4-dione 、 4-(4-Bromo-benzyloxy)-6-(4-bromo-phenyl)-3,5,5-trimethyl-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  摘要：

  Zinc enolates of 3-alkyl-6-aryl-5,5-dimethyl-2,3,5,6-tetrahydropyrane-2,4-diones react with acyl chlorides to form O-acylation products, 4-acyloxy-3-alkyl-6-aryl-5,5-dimethyl-5,6-dihydropyrane-2-ones. Sodium enolates of these pyranediones react in DMSO with substituted benzyl bromides to give mainly C-alkylation products, 3-alkyl-6-aryl-3-(4-R-benzyl)-5,5-dimethyl-2,3,5,6-tetrahydropyrane-2,4-diones, as single geometric isomers. In some cases, O-alkylation products, 4-alkoxy-3-alkyl-6-aryl-5,5-dimethyl-5,6-dihydropyrane-2-ones, are formed as by-products (similar to10-15%).

  DOI：

  10.1023/a:1026191021119

文献信息

• ——
  作者：V. V. Shchepin、Yu. Kh. Sazhneva、N. Yu. Russkikh、M. I. Vakhrin

  DOI：10.1023/a:1026191021119

  日期：——

  Zinc enolates of 3-alkyl-6-aryl-5,5-dimethyl-2,3,5,6-tetrahydropyrane-2,4-diones react with acyl chlorides to form O-acylation products, 4-acyloxy-3-alkyl-6-aryl-5,5-dimethyl-5,6-dihydropyrane-2-ones. Sodium enolates of these pyranediones react in DMSO with substituted benzyl bromides to give mainly C-alkylation products, 3-alkyl-6-aryl-3-(4-R-benzyl)-5,5-dimethyl-2,3,5,6-tetrahydropyrane-2,4-diones, as single geometric isomers. In some cases, O-alkylation products, 4-alkoxy-3-alkyl-6-aryl-5,5-dimethyl-5,6-dihydropyrane-2-ones, are formed as by-products (similar to10-15%).