(E)-3-benzylidene-4-phenylbutan-2-one | 123707-47-1

• 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: (E)-3-benzylidene-4-phenylbutan-2-one
• 英文别名: (E)-3-benzyl-4-phenyl-3-buten-2-one；(E)-3-benzyl-4-phenylbut-3-en-2-one；3-benzyl-4-phenylbut-3-en-2-one
• CAS: 123707-47-1
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: PSFURMCBWJQCRX-SFQUDFHCSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  386.3±21.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：

  (5R,6S)-5-Benzyl-6-phenyl-dihydro-pyran-2,4-dione 在 potassium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以74%的产率得到(E)-3-benzylidene-4-phenylbutan-2-one
  参考文献：
  名称：

  Novel synthesis of indan derivatives.

  摘要：

  在进行与生物活性化合物相关的5,6-二取代4-氧代四氢-2-吡喃酮骨架的合成研究过程中，我们发现了一种便捷的方法，可以区域选择性地在甲基烷基酮中引入双键，并开发了一种新颖的茚衍生物合成方法。

  DOI：

  10.1248/cpb.34.4527

文献信息

• Sequential Reactions of Michael Addition and Peterson Condensation of 1-Silylvinyl Ketones with Grignard Reagents: Study of Stereoselectivity
  作者：Junji Tanaka、Hiroshi Kobayashi、Shuji Kanemasa、Otohiko Tsuge

  DOI：10.1246/bcsj.62.1193

  日期：1989.4.15

  1-Silylvinyl ketones undergo smooth Michael addition with Grignard reagents generating magnesium enolates which are then trapped with benzaldehyde to give E- and Z-isomers of enones after Peterson condensation. (E)-Olefins become major products under a thermodynamic control when the condensation with benzaldehyde is carried out at room temperature in diethyl ether, while Z-isomers are more favored

  1-甲硅烷基乙烯基酮与格氏试剂进行平滑的迈克尔加成，生成烯醇镁，然后在彼得森缩合后用苯甲醛捕获烯酮的 E- 和 Z-异构体。当与苯甲醛在室温下在乙醚中缩合时，(E)-烯烃成为热力学控制下的主要产物，而 Z-异构体在-78°C 的 THF 中作为动力学控制的产物更受欢迎。简要讨论了反应机理。
• Stereospecific Synthesis of Methyl Vinyl Ketones
  作者：A. Chamakh、M. M'hirsi、H. Amri

  DOI：10.1080/00397919708003352

  日期：1997.4

  Abstract A stereospecific synthesis of enones 3 by coupling reaction of α-acetoxy alkyl methyl vinyl ketones 2 and Gilman or Grignard reagents in the presence of a catalytic amount of copper (I) salt at low temperature, is described.

  摘要 描述了在催化量的铜 (I) 盐存在下，通过 α-乙酰氧基烷基甲基乙烯基酮 2 与吉尔曼或格利雅试剂的偶联反应，在低温下立体有择地合成烯酮 3。
• Copper-Catalyzed α-Benzylation of Enones via Radical-Triggered Oxidative Coupling of Two C–H Bonds
  作者：Guiping Qin、Xiangning Chen、Lei Yang、Hanmin Huang

  DOI：10.1021/acscatal.5b00310

  日期：2015.5.1

  A novel copper(II)-catalyzed, regioselective C-H benzylation of enones with toluenes via radical triggered oxidative coupling has been developed. A series of enones and toluenes with different substituents were successfully incorporated, providing a wide range of alpha-benzylated enones with TBP as oxidant by cleavage of C(sp(3)) H bond and C(sp(2)) H bond. Preliminary mechanistic study reveals a benzylic carbon radical is generated, and regioselectively reacts with enones to deliver the corresponding products.
• Palladium-Catalyzed Cross-Coupling of Baylis−Hillman Acetate Adducts with Organosilanes
  作者：George W. Kabalka、Gang Dong、Bollu Venkataiah、Chunlan Chen

  DOI：10.1021/jo051177k

  日期：2005.11.1

  A cross-coupling reaction between acetates of Baylis-Hillman adducts and organosilanes is described. A nonconventional solvent poly(ethylene glycol) (PEG) is used as the reaction medium.
• TANAKA, JUNJI;KOBAYASHI, HIROSHI;KANEMASA, SHUJI;TSUGE, OTOHIKO, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1193-1197
  作者：TANAKA, JUNJI、KOBAYASHI, HIROSHI、KANEMASA, SHUJI、TSUGE, OTOHIKO

  DOI：——

  日期：——