2′-acetylbiphenyl-4-carbaldehyde | 400750-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2′-acetylbiphenyl-4-carbaldehyde
• 英文别名: 4-formyl-2'-acetylbiphenyl；4-(2-Acetylphenyl)benzaldehyde
• CAS: 400750-43-8
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: ISPRMRCTKPAWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,5,7,8-tetrahydro-2-(4'-formylphenyl)-6H-[1,3,6,2]dioxazaborocane 、 2-acetylbenzenediazonium tetrafluoroborate 在 1% Pd/C 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以20%的产率得到2′-acetylbiphenyl-4-carbaldehyde
  参考文献：
  名称：

  Base free aryl coupling of diazonium compounds and boronic esters: self-activation allowing an overall highly practical process

  摘要：

  长期以来，硼酸酯一直被认为是与芳烃重氮盐发生交叉偶联反应的不良伙伴。本文报告了自活化硼酸酯在温和友好的条件下与重氮盐进行无碱交叉偶联反应中的前所未有的应用。

  DOI：

  10.1039/b926547n

文献信息

• CuBr₂-Mediated One-Pot Synthesis of Sulfonyl 9-Fluorenylidenes
  作者：Meng-Yang Chang、Yu-Lin Tsai、Hsing-Yin Chen

  DOI：10.1021/acs.joc.0c00035

  日期：2020.6.5

  In this article, a high-yield method for the synthesis of sulfonyl 9-fluorenylidenes is described, which consists of a one-pot straightforward three-step synthetic route, including (i) CuBr2-mediated alpha-bromination of o-arylacetophenone, (ii) sequential nucleophilic substitution of the resulting alpha-bromo o-arylacetophenone with sodium sulfinate (RSO2Na), and (iii) the CuBr2-mediated intramolecular Friedel-Crafts cyclizative dehydration. A plausible mechanism is proposed and discussed. This protocol provides a highly effective regio- and stereoselective annulation via the formation of one carbon-carbon (C-C) bond and one carbon-sulfur (C-S) bond.
• Base free aryl coupling of diazonium compounds and boronic esters: self-activation allowing an overall highly practical process
  作者：Hélène Bonin、Dominique Delbrayelle、Patrice Demonchaux、Emmanuel Gras

  DOI：10.1039/b926547n

  日期：——

  Boronic esters have long been considered as poor partners in cross-coupling reactions with arene diazoniums. Here is reported an unprecedented application of self-activated boronic esters in a base-free cross-coupling reaction with diazonium salts under mild and user friendly conditions.

  长期以来，硼酸酯一直被认为是与芳烃重氮盐发生交叉偶联反应的不良伙伴。本文报告了自活化硼酸酯在温和友好的条件下与重氮盐进行无碱交叉偶联反应中的前所未有的应用。