2-methyl-1,3-diphenylbut-3-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-methyl-1,3-diphenylbut-3-en-1-one
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: KXNSNXAAWXZBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  alpha- 溴苯乙烯 、 苯丙酮 在 1,2,3,4,5-五苯基-1′-(二叔丁基膦)二茂铁 、 palladium diacetate 、 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以71%的产率得到2-methyl-1,3-diphenylbut-3-en-1-one
  参考文献：
  名称：

  Palladium-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions

  摘要：

  A protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates has been developed using a Pd/Q-Phos catalyst. Efficient intermolecular coupling of a variety of ketones with alkenyl bromides was achieved with a slight excess of LiHMDS and temperatures down to 0 °C.

  DOI：

  10.1021/ol5017965

文献信息

• Ethenylation of Silyl Enol Ether with Silylethyne
  作者：Masahiko Yamaguchi、Toru Tsukagoshi、Mieko Arisawa

  DOI：10.1021/ja984022l

  日期：1999.4.1
• Palladium-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions
  作者：Michael Grigalunas、Tobias Ankner、Per-Ola Norrby、Olaf Wiest、Paul Helquist

  DOI：10.1021/ol5017965

  日期：2014.8.1

  A protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates has been developed using a Pd/Q-Phos catalyst. Efficient intermolecular coupling of a variety of ketones with alkenyl bromides was achieved with a slight excess of LiHMDS and temperatures down to 0 °C.
• Ni-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions: Catalyst Identification and Optimization
  作者：Michael Grigalunas、Tobias Ankner、Per-Ola Norrby、Olaf Wiest、Paul Helquist

  DOI：10.1021/jacs.5b02945

  日期：2015.6.10

  A procedure for Ni-catalyzed cross-coupling of ketone enolates with alkenyl halides has been developed. Intermolecular coupling of aromatic and aliphatic ketone lithium enolates with a variety of alkenyl halides is achieved in the presence of Ni(cod)(2) catalyst (5 mol %), an N-heterocyclic carbene (NHC) ligand, and LiI (10 mol %) at 6-22 degrees C for 0.5-12 h with yields of up to 90%. During the initial development of this reaction, a misleading result with respect to the actual active catalyst was obtained using commercially available Q:Phos ligand, which was found to contain a trace of Pd metal contaminant sufficient to catalyze the reaction. However, under the final conditions optimized for Ni(cod)(2) in the presence of an NHC ligand, Pd was incompetent as a catalyst.