methyl 4-(2,2-diphenylacetyl)benzoate | 1259024-99-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 4-(2,2-diphenylacetyl)benzoate
• 英文别名: Methyl 4-(2,2-diphenylacetyl)benzoate
• CAS: 1259024-99-1
• 化学式: C₂₂H₁₈O₃
• 分子量: 330.383
• InChiKey: MFHRYSWTYWPYFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  二苯基溴甲烷 、 对甲酰基苯甲酸甲酯 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到methyl 4-(2,2-diphenylacetyl)benzoate
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aromatic Aldehydes with Activated Alkyl Halides

  摘要：

  N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, a-halo ketones and esters can also be used, as aldehyde reaction partners.

  DOI：

  10.1021/ol102626p

文献信息

• Carbene-Catalyzed Alkylation of Carboxylic Esters via Direct Photoexcitation of Acyl Azolium Intermediates
  作者：Shi-Chao Ren、Wen-Xin Lv、Xing Yang、Jia-Lei Yan、Jun Xu、Fang-Xin Wang、Lin Hao、Huifang Chai、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/acscatal.1c00165

  日期：2021.3.5

  A carbene-catalyzed reductive coupling reaction of carboxylic esters and substituted Hantzsch esters is disclosed. Key steps of this reaction include one-electron reduction of a carbene catalyst-bound acyl azolium intermediate to generate the corresponding radical intermediate for subsequent alkylation reactions. The reaction is promoted by irradiation with visible light without the involvement of

  公开了羧酸酯和取代的汉茨tz酯的卡宾催化的还原偶联反应。该反应的关键步骤包括单电子还原卡宾催化剂所结合的酰基偶氮中间体，以产生相应的自由基中间体用于随后的烷基化反应。在不涉及过渡金属光催化剂的情况下，通过可见光照射可促进反应。机理研究表明，原位形成的酰基偶氮鎓中间体的直接光激发可能是这种光诱导的单电子还原过程的原因。光激发将酰基偶氮中间体转化为单电子氧化剂，从而使Hantzsch酯进行单电子氧化以生成自由基中间体。我们的反应适用于各种芳基羧酸酯和Hantzsch酯底物。可以使用我们的方法，通过非常温和的条件（可以耐受各种官能团）将复杂的结构（包括药物中存在的结构）并入酮分子中。
• N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aromatic Aldehydes with Activated Alkyl Halides
  作者：Mohan Padmanaban、Akkattu T. Biju、Frank Glorius

  DOI：10.1021/ol102626p

  日期：2011.1.7

  N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, a-halo ketones and esters can also be used, as aldehyde reaction partners.