[3-(3,4-dimethoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)-methanone | 861881-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-(3,4-dimethoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)-methanone
• 英文别名: Methanone, [3-(3,4-dimethoxyphenyl)oxiranyl](4-methoxyphenyl)-；[3-(3,4-dimethoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)methanone
• CAS: 861881-87-0
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: OYHUVSXXTRGUON-UHFFFAOYSA-N

物化性质

• 沸点：
  480.5±45.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  呋喃 、 [3-(3,4-dimethoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)-methanone 在 lithium perchlorate 、 2-(4-bromophenyl)-1-methyl-4,5-diphenyl-1H-imidazole 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以16%的产率得到3-(3,4-dimethoxyphenyl)-3-(furan-2-yl)-2-hydroxy-1-(4-methoxypheny)propan-1-one
  参考文献：
  名称：

  Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator

  摘要：

  The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med(center dot+) and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel-Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med(center dot+) initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.

  DOI：

  10.1021/jo5022184
• 作为产物：
  描述：

  3-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以89%的产率得到[3-(3,4-dimethoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)-methanone
  参考文献：
  名称：

  Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator

  摘要：

  The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med(center dot+) and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel-Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med(center dot+) initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.

  DOI：

  10.1021/jo5022184