2-bromo-4,4'-dimethoxybenzophenone

• 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-4,4'-dimethoxybenzophenone
• 英文别名: (2-Bromo-4-methoxyphenyl)(4-methoxyphenyl)methanone；(2-bromo-4-methoxyphenyl)-(4-methoxyphenyl)methanone
• 化学式: C₁₅H₁₃BrO₃
• 分子量: 321.17
• InChiKey: NSELRAIXBHFDSA-UHFFFAOYSA-N

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：
  0.13
• 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-4,4'-dimethoxybenzophenone 在 溴 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(3-bromo-4-methoxyphenyl)(2,5-dibromo-4-methoxyphenyl)methanone
  参考文献：
  名称：

  新型溴酚的合成和表征：测定其抗胆碱能，抗糖尿病和抗氧化活性。

  摘要：

  本文合成了一系列新型的溴酚衍生物，并对其乙酰胆碱酯酶和α-糖苷酶的抑制特性和抗氧化活性进行了评估。合成了二芳基甲烷酮，并进行了溴化反应。在溴化过程中，一些化合物通过区域选择性的O-去甲基化生成了新的溴酚。溴化二芳基甲烷也用BBr 3脱甲基，得到新的溴酚。此外，我们使用几种体外生物分析方法，例如2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸）（ABTS⋅ +）和1,1-二苯基- 2-吡啶甲酰肼基自由基（DPPH ）清除活性，Fe 3+Cu 2+还原活性和亚铁（Fe 2+）离子螯合活性。此外，还测试了新型溴酚和甲氧基化溴酚衍生物的抗乙酰胆碱酯酶和α-糖苷酶的作用，这些酶与某些代谢性疾病有关。新型溴酚对AChE的Ki值在8.94±0.73–59.45±14.97 nM的范围内，对α-糖苷酶的Ki值在4.31±1.93–44.14±2.19 nM的范围内。

  DOI：

  10.1016/j.bioorg.2019.03.010
• 作为产物：
  描述：

  4-溴苯甲醚 、 间溴苯甲醚 、 1,1-二氯甲醚 以60%的产率得到2-bromo-4,4'-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

文献信息

• Photoinduced C−Br Homolysis of 2-Bromobenzophenones and Pschorr Ring Closure of 2-Aroylaryl Radicals to Fluorenones
  作者：Jarugu Narasimha Moorthy、Subhas Samanta

  DOI：10.1021/jo7017872

  日期：2007.12.1

  [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.
• Synthesis and characterization of novel bromophenols: Determination of their anticholinergic, antidiabetic and antioxidant activities
  作者：Necla Öztaşkın、Rüya Kaya、Ahmet Maraş、Ertan Şahin、İlhami Gülcin、Süleyman Göksu

  DOI：10.1016/j.bioorg.2019.03.010

  日期：2019.6

  In this paper, a series of novel bromophenol derivatives were synthesized and evaluated for their acetylcholinesterase and α-glycosidase enzymes inhibition properties and antioxidant activity. Diarylmethanones were synthesized and their bromination was carried out. During bromination, some compounds gave new bromophenols via regioselective O-demethylation. Demethylation of brominated diarylmethanones

  本文合成了一系列新型的溴酚衍生物，并对其乙酰胆碱酯酶和α-糖苷酶的抑制特性和抗氧化活性进行了评估。合成了二芳基甲烷酮，并进行了溴化反应。在溴化过程中，一些化合物通过区域选择性的O-去甲基化生成了新的溴酚。溴化二芳基甲烷也用BBr 3脱甲基，得到新的溴酚。此外，我们使用几种体外生物分析方法，例如2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸）（ABTS⋅ +）和1,1-二苯基- 2-吡啶甲酰肼基自由基（DPPH ）清除活性，Fe 3+Cu 2+还原活性和亚铁（Fe 2+）离子螯合活性。此外，还测试了新型溴酚和甲氧基化溴酚衍生物的抗乙酰胆碱酯酶和α-糖苷酶的作用，这些酶与某些代谢性疾病有关。新型溴酚对AChE的Ki值在8.94±0.73–59.45±14.97 nM的范围内，对α-糖苷酶的Ki值在4.31±1.93–44.14±2.19 nM的范围内。