[3-(3,4-dimethoxyphenyl)oxiran-2-yl]phenylmethanone | 107418-77-9

• 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]phenylmethanone
• 英文别名: 3-(3,4-dimethoxy-phenyl)-2,3-epoxy-1-phenyl-propan-1-one；3-(3,4-Dimethoxy-phenyl)-2,3-epoxy-1-phenyl-propan-1-on；[3-(3,4-Dimethoxyphenyl)oxiran-2-yl]-phenylmethanone
• CAS: 107418-77-9
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: JSPRPOJTEAHBPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-(3,4-dimethoxyphenyl)oxiran-2-yl]phenylmethanone 、 尿素 在 氢氧化钾 作用下， 生成 5-phenyl-5-veratryl-imidazolidine-2,4-dione
  参考文献：
  名称：

  Enebaeck, Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 1528

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基查耳酮 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以90%的产率得到[3-(3,4-dimethoxyphenyl)oxiran-2-yl]phenylmethanone
  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

文献信息

• Algar; McKenna, Proceedings of the Royal Irish Academy, Section B: Biological, Geological and Chemical Science, 1943, vol. 49 B, p. 225,233
  作者：Algar、McKenna

  DOI：——

  日期：——
• Enebaeck, Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 1528
  作者：Enebaeck

  DOI：——

  日期：——
• Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator
  作者：Nan-ning Lu、Ni-tao Zhang、Cheng-Chu Zeng、Li-Ming Hu、Seung Joon Yoo、R. Daniel Little

  DOI：10.1021/jo5022184

  日期：2015.1.16

  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.