{2-[(1E)-1,2-diphenylethenyl]phenyl}-1-pyrrolidinylmethanone | 1110635-82-9

• 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: {2-[(1E)-1,2-diphenylethenyl]phenyl}-1-pyrrolidinylmethanone
• 英文别名: (2-(1,2-diphenylvinyl)phenyl)pyrrolidin-1-ylmethanone；[2-[(E)-1,2-diphenylethenyl]phenyl]-pyrrolidin-1-ylmethanone
• CAS: 1110635-82-9
• 化学式: C₂₅H₂₃NO
• 分子量: 353.464
• InChiKey: GALKCNROLMZQOB-LYBHJNIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  苯基(1-吡咯烷基)甲酮 、 二苯基乙炔 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79%的产率得到{2-[(1E)-1,2-diphenylethenyl]phenyl}-1-pyrrolidinylmethanone
  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

• Ruthenium(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes via Directed C–H Functionalization
  作者：Yuto Hashimoto、Koji Hirano、Tetsuya Satoh、Fumitoshi Kakiuchi、Masahiro Miura

  DOI：10.1021/ol300579m

  日期：2012.4.20

  The ruthenium-catalyzed hydroarylation of alkynes with benzamides proceeds regio- and stereoselectively through a directed C–H bond cleavage. Preliminary mechanistic investigations indicate that the reaction involves amide-directed ortho-metalation, carbometalation of alkyne, and protonolysis. Similarly, phenylazoles also add to alkynes regioselectively.

  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。
• Amide-Directed Alkenylation of sp² C−H Bonds Catalyzed by a Cationic Rh(I)/BIPHEP Complex Under Mild Conditions: Dramatic Rate Acceleration by a 1-Pyrrolidinecarbonyl Group
  作者：Yu Shibata、Yousuke Otake、Masao Hirano、Ken Tanaka

  DOI：10.1021/ol802767s

  日期：2009.2.5

  A cationic rhodium(I)/BIPHEP complex catalyzes amide-directed regioselective alkenylations of olefinic or aromatic sp(2) C-H bonds in good yields under mild reaction conditions. The use of a 1-pyrrolidinecarbonyl group as a directing group dramatically accelerates the reaction.
• 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.