(Z)-1-(2-(1,2-diphenylvinyl)phenyl)ethanone | 1101863-60-8

• 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: (Z)-1-(2-(1,2-diphenylvinyl)phenyl)ethanone
• 英文别名: 1-(2-(1,2-diphenylvinyl)phenyl)ethanone
• CAS: 1101863-60-8
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: XOIHRTOVAZTPBD-JWGURIENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-(2-(1,2-diphenylvinyl)phenyl)ethanone 在 tetrakis(trimethylphosphine)cobalt(0) 作用下， 以 甲苯 为溶剂， 生成 (E)-1-[2-(1,2-diphenylvinyl)phenyl]ethanone
  参考文献：
  名称：

  C–H Activation/Functionalization Catalyzed by Simple, Well-Defined Low-Valent Cobalt Complexes

  摘要：

  A facile C-H activation and functionalization of aromatic imines is presented using low-valent cobalt catalysts. Using Co(PMe3)(4) as catalyst we have developed an efficient and simple protocol for the C-H/hydroarylation of alkynes with an anti selectivity. Deuterium-labeling experiments, DFT calculations coupled with the use of a well-defined catalyst have for the first time shed light on the elusive black box of cobalt catalyzed C-H functionalization.

  DOI：

  10.1021/ja512728f
• 作为产物：
  描述：

  1-(2-(phenylethynyl)phenyl)ethanol 、 苯磺酰氯 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以45%的产率得到(Z)-1-(2-(1,2-diphenylvinyl)phenyl)ethanone
  参考文献：
  名称：

  Redox-triggered hydroarylation of o-(hydroxyalkyl)arylalkynes with arylsulfonyl chlorides using visible light catalysis

  摘要：

  报道了一种通过邻（羟基烷基）芳基炔与芳基磺酰氯的氧化性氢芳基化反应，合成1-(2-(1,2-二芳基乙烯)苯基)乙酮的新型自由基介导方法。该可见光催化方法通过一系列反应过程实现，包括芳基团对碳-碳叁键的自由基加成、质子化和氧化还原反应，并代表了一种由邻位羟基引导的新型氧化还原转化反应。

  DOI：

  10.1007/s11426-015-5529-0

文献信息

• Cobalt-Catalyzed, Room-Temperature Addition of Aromatic Imines to Alkynes via Directed C–H Bond Activation
  作者：Pin-Sheng Lee、Takeshi Fujita、Naohiko Yoshikai

  DOI：10.1021/ja2047073

  日期：2011.11.2

  A quaternary catalytic system consisting of a cobalt salt, a triarylphosphine ligand, a Grignard reagent, and pyridine has been developed for chelation-assisted C-H bond activation of an aromatic imine, followed by insertion of an unactivated internal alkyne that occurs at ambient temperature. The reaction not only tolerates potentially senstitive functional groups (e.g., Cl, Br, CN, and tertiary amide)

  已开发出由钴盐、三芳基膦配体、格氏试剂和吡啶组成的四元催化系统，用于芳族亚胺的螯合辅助 CH 键活化，然后在环境温度下插入未活化的内部炔。该反应不仅可以耐受潜在的敏感官能团（例如，Cl、Br、CN 和叔酰胺），而且还显示出独特的区域选择性。因此，在亚氨基间位的取代基如甲氧基、卤素和氰基的存在导致在空间位阻更大的邻位选择性形成CC键。在酸性条件下，二烷基-和烷基芳基乙炔的加氢芳基化产物经过环化得到苯并富烯衍生物，而二芳基乙炔的那些以中等至良好的产率提供相应的酮。借助氘标记实验和动力学分析对反应进行的机理研究表明，邻位 CH 键的氧化加成是反应的限速步骤。动力学分析还揭示了四元催化系统的复杂性。
• Ruthenium(0)-catalyzed hydroarylation of alkynes via ketone-directed C–H functionalization using in situ-generated ruthenium complexes
  作者：Feng Hu、Michal Szostak

  DOI：10.1039/c6cc04537e

  日期：——

  Ketone-directed Ru(0)-catalyzed hydroarylation of alkynes enabled by in situ generation of a Ru(0) catalyst from an air-stable, inexpensive and user-friendly Ru(II) precatalyst is reported.

  据报道，通过从稳定的，便宜的和用户友好的Ru（II）预催化剂原位生成Ru（0）催化剂，可以实现酮类Ru-（0）催化的炔烃加氢芳基化反应。
• Cationic iridium–BINAP complex-catalyzed addition of aryl ketones to alkynes and alkenes via directed C–H bond cleavage
  作者：Kyoji Tsuchikama、Mitsugu Kasagawa、Yu-Ki Hashimoto、Kohei Endo、Takanori Shibata

  DOI：10.1016/j.jorganchem.2008.09.065

  日期：2008.12

  Cationic Ir complex ([Ir(cod)2]BF4 + BINAP) catalyzed the addition of ortho-C–H bonds in aryl ketones to alkynes, which gave alkenylated products in good to high yield. Styrene derivatives were good substrates, and the enantioselective addition to norbornene was also described.

  阳离子Ir络合物（[Ir（cod）2 ] BF 4  + BINAP）催化芳基酮中的邻位C-H键加成至炔烃，从而以高收率得到高收率的烯化产物。苯乙烯衍生物是良好的底物，并且还描述了降冰片烯的对映选择性加成。
• Cobalt-Catalyzed Hydroarylation of Alkynes through Chelation-Assisted C−H Bond Activation
  作者：Ke Gao、Pin-Sheng Lee、Takeshi Fujita、Naohiko Yoshikai

  DOI：10.1021/ja106814p

  日期：2010.9.8

  Ternary catalytic systems consisting of cobalt salts, phosphine ligands, and Grignard reagents promote addition of arylpyridines and imines to unactivated internal alkynes with high regio- and stereoselectivities. Deuterium-labeling experiments suggest that the reaction involves chelation-assisted oxidative addition of the aryl C-H bond to the cobalt center and insertion of the C-C triple bond into the Co-H bond, followed by reductive elimination of the resulting diorganocobalt species.