[1,1′-biphenyl]-2-yl(p-tolyl)methanone | 113449-31-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: [1,1′-biphenyl]-2-yl(p-tolyl)methanone
• 英文别名: ([1,1'-Biphenyl]-2-yl)(4-methylphenyl)methanone；(4-methylphenyl)-(2-phenylphenyl)methanone
• CAS: 113449-31-3
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: WWVMATARFOVKRE-UHFFFAOYSA-N

物化性质

• 沸点：
  464.3±24.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1,1′-biphenyl]-2-yl(p-tolyl)methanone 以70%的产率得到
  参考文献：
  名称：

  SAITO, TAKAO;KIKUCHI, YASUHISA;SUMIZAWA, NORIO;MOTOKI, SHINICHI, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1987) N 7, 1385-1392

  摘要：

  DOI：
• 作为产物：
  描述：

  二氢-3-(异十二碳烯基)呋喃-2,5-二酮 在 aluminum (III) chloride 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 [1,1′-biphenyl]-2-yl(p-tolyl)methanone
  参考文献：
  名称：

  芳基邻联芳基酮中的6-芳基菲啶与1,1,1,3,3,3-六甲基二硅氮杂和分子碘

  摘要：

  在甲苯中Sc（OTf）3存在下，通过与1,1,1,1,3,3,3-六甲基二硅氮烷反应，将芳基联芳基酮有效地转化为6-芳基菲啶，然后除去溶剂，然后进行后续反应分子碘和THF和甲醇的混合物中的K 2 CO 3。

  DOI：

  10.1002/ejoc.201901278

文献信息

• One-Pot Synthesis of Polysubstituted Spirofluorene–Indene via Ru(II)-Catalyzed [3 + 2] Annulation and Intramolecular Friedel–Crafts Cyclization
  作者：Yu-Qin Zhu、Lin Dong

  DOI：10.1021/acs.joc.5b01517

  日期：2015.10.16

  Ru(II)-catalyzed one-pot synthesis of polysubstituted spirofluorene–indenes via [3 + 2] annulation and then intramolecular Friedel–Crafts alkylation has been achieved. The simple method provides a broad scope of aryl ketones and internal alkynes, achieving PAHs skeletons in moderate to good yields.

  Ru（II）通过[3 + 2]环化催化一锅法合成多取代的螺芴-茚，然后实现了分子内Friedel-Crafts烷基化。这种简单的方法提供了广泛的芳基酮和内部炔烃，以中等到良好的产率获得了PAHs骨架。
• Divergent Synthesis of Highly Substituted Pyridines and Benzenes from Dienals, Alkynes, and Sulfonyl Azides
  作者：Han Luo、You Li、Luan Du、Xiaolan Xin、Tao Wang、Jingpeng Han、Yi Tian、Baosheng Li

  DOI：10.1021/acs.orglett.1c02900

  日期：2021.10.15

  Divergent synthesis is extremely important for the highly efficient preparation of structurally diverse target molecules. Herein, we describe a multicomponent cascade reaction, which allows access to highly substituted pyridines and benzenes by combining four individual steps in a one-pot manner from the same set of readily available starting materials. The azepine intermediates were first used as

  发散合成对于高效制备结构多样的目标分子极为重要。在此，我们描述了一种多组分级联反应，该反应允许通过将四个单独的步骤以一锅法从同一组容易获得的起始材料中组合来获得高度取代的吡啶和苯。氮杂中间体首先用作 6π 电环化的前体，以可调节的方式构建高度取代的吡啶和苯。
• Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using 2-Chloroimidazolium Chloride as a Coupling Reagent
  作者：Yan Zhang、Yuan-Hua Wang、Qi-Wei Wang、Wei-Xiang Zheng、Jing Zhong、Yi-Ting Yang、Meluze Luobu

  DOI：10.1055/a-1848-3399

  日期：2022.10

  Carboxylic acids are an abundant and structurally diverse class of commercially available materials, which are commonly used as stable reagents in organic synthesis. The Suzuki–Miyaura coupling reaction directly using carboxylic acid as a substrate has been rarely reported. Here, we report an efficient coupling reaction of carboxylic acids with arylboronic acids in toluene in the presence of IPrCl-Cl

  羧酸是一种丰富且结构多样的市售材料，通常用作有机合成中的稳定试剂。很少报道直接使用羧酸作为底物的 Suzuki-Miyaura 偶联反应。在此，我们报道了在 IPrCl-Cl、Pd(OAc) 2、PPh 3和 K 3 PO 4 ·7H 2 O存在下，羧酸与芳基硼酸在甲苯中在 90 °C 下的有效偶联反应，得到相应的芳基酮。
• Chiral TPE Foldamers in Macrocycles: Aggregation Enhanced Emission and Circularly Polarized Luminescence
  作者：Yuxiang Wang、Liwen Cui、Yiran Wang、Fei Li、Yunzhi Li、Qi Meng

  DOI：10.1002/chem.202302373

  日期：2023.12.6

  Chiral TPE foldamers were first constructed through macrocycle architectonics and the chiroptical properties were investigated. Aggregation enhanced emission and unusual circularly polarized luminescence can be discovered due to the folded conformation.

  首先通过大环结构学构建了手性 TPE 折叠体，并研究了手性光学特性。由于折叠构象，可以发现聚集增强的发射和不寻常的圆偏振发光。
• Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines
  作者：Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1021/acs.orglett.5b00797

  日期：2015.5.1

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.