(E)-2-(1,2-diphenylethenyl)-N,N-dimethylbenzamide | 1370704-87-2

• 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: (E)-2-(1,2-diphenylethenyl)-N,N-dimethylbenzamide
• 英文别名: 2-[(E)-1,2-diphenylethenyl]-N,N-dimethylbenzamide
• CAS: 1370704-87-2
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: BQQDYMUNIJQYQP-OQKWZONESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基乙炔 、 N,N-二甲基苯甲酰胺 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以81%的产率得到(E)-2-(1,2-diphenylethenyl)-N,N-dimethylbenzamide
  参考文献：
  名称：

  钌（II）催化的C–H官能化催化炔烃的区域和立体选择性加氢芳基化

  摘要：

  钌与苯甲酰胺催化的炔烃加氢芳基化反应通过定向C–H键断裂在区域和立体选择性上进行。初步的机理研究表明该反应涉及酰胺定向的原金属化，炔烃的碳金属化和质子分解。类似地，苯唑也可以区域选择性地添加到炔烃中。

  DOI：

  10.1021/ol300579m

文献信息

• Regioselective C–H Bond Cleavage/Alkyne Insertion under Ruthenium Catalysis
  作者：Yuto Hashimoto、Koji Hirano、Tetsuya Satoh、Fumitoshi Kakiuchi、Masahiro Miura

  DOI：10.1021/jo3025237

  日期：2013.1.18

  The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.
• Cationic Ir(I)-Catalyzed sp³ C−H Bond Alkenylation of Amides with Alkynes
  作者：Kyoji Tsuchikama、Mitsugu Kasagawa、Kohei Endo、Takanori Shibata

  DOI：10.1021/ol900404r

  日期：2009.4.16

  A cationic Ir(I)-BINAP catalyst cleaved sp(3) C-H bonds of arylamides rather than sp(2) C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp(3) C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.