2-bromo-3',5'-dimethoxybenzophenone | 951892-04-9

• 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: 2-bromo-3',5'-dimethoxybenzophenone
• 英文别名: (2-bromophenyl)-(3,5-dimethoxyphenyl)methanone
• CAS: 951892-04-9
• 化学式: C₁₅H₁₃BrO₃
• mdl: MFCD09801534
• 分子量: 321.17
• InChiKey: ZRTJMTZHOYTQGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  442.0±40.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3',5'-dimethoxybenzophenone 以 乙腈 为溶剂， 反应 72.0h， 以80%的产率得到2,4-dimethoxy-9H-fluoren-9-one
  参考文献：
  名称：

  Photoinduced C−Br Homolysis of 2-Bromobenzophenones and Pschorr Ring Closure of 2-Aroylaryl Radicals to Fluorenones

  摘要：

  [Graphics]A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl sigma-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl pi-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.

  DOI：

  10.1021/jo7017872
• 作为产物：
  描述：

  (2-Bromophenyl)-(3,5-dimethoxyphenyl)methanol 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到2-bromo-3',5'-dimethoxybenzophenone
  参考文献：
  名称：

  Photoinduced C−Br Homolysis of 2-Bromobenzophenones and Pschorr Ring Closure of 2-Aroylaryl Radicals to Fluorenones

  摘要：

  [Graphics]A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl sigma-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl pi-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.

  DOI：

  10.1021/jo7017872