E/Z ethyl (4-benzoyl-3-methylene-1-butenyl)ether | 549504-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: E/Z ethyl (4-benzoyl-3-methylene-1-butenyl)ether
• 英文别名: ethyl 4-benzoyloxy-3-methylene-1-butenyl ether；(4-ethoxy-2-methylidenebut-3-enyl) benzoate
• CAS: 549504-65-6
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: RBPIHNAWFXMGAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 E/Z ethyl (4-benzoyl-3-methylene-1-butenyl)ether 在 对苯二酚 作用下， 以 甲苯 为溶剂， 反应 66.0h， 以94.6 mg的产率得到(7-ethoxy-2-methyl-1,3-dioxo-2,3,3',4,7,7'-hexahydro-1H-isoindol-5-yl)methyl benzoate
  参考文献：
  名称：

  Intermolecular Enol Ether−Alkyne Metathesis

  摘要：

  [GRAPHICS]A new intermolecular metathesis between a variety of alkynes and alkyl enol ethers is described. The best results were obtained with the second generation Grubbs' precatalysts. The reaction occurred with a high degree of regioselectivity and provided electron-rich dienes, which underwent a variety of [4 + 2] cycloadditions.

  DOI：

  10.1021/ol034459k
• 作为产物：
  描述：

  苯酸炔丙酯 、 乙烯基乙醚 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 苯 为溶剂， 反应 0.17h， 以98%的产率得到E/Z ethyl (4-benzoyl-3-methylene-1-butenyl)ether
  参考文献：
  名称：

  Metal Carbene-Promoted Sequential Transformations for the Enantioselective Synthesis of Highly Functionalized Cycloheptadienes

  摘要：

  A two-step, three-component coupling of an alkyne, enol ether, and vinyl diazoester was accomplished by use of successive metal carbene-catalyzed transformations. This efficient approach to cycloheptadienes is both diastereo- and enantioselective. Kinetic resolution was accomplished on dienol ethers bearing a racemic chiral center at the propargylic position. A model is offered which explains the observed selectivity and accounts for the reactivity difference between trans- and cis-dienol ethers.

  DOI：

  10.1021/ja045173t

文献信息

• Alkyne-Enol Ether Cross-Metathesis in the Presence of CuSO₄: Direct Formation of 3-Substituted Crotonaldehydes in Aqueous Medium
  作者：Daniele Castagnolo、Lorenzo Botta、Maurizio Botta

  DOI：10.1021/jo900205x

  日期：2009.4.17

  An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO4 and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from terminal alkyl-alkynes. All of the reactions were carried out under microwave irradiation and were completed in a few minutes. Water was used as the cosolvent, making c, this approach safer, economic, and desiderable from an enviromental point of view.
• Metal Carbene-Promoted Sequential Transformations for the Enantioselective Synthesis of Highly Functionalized Cycloheptadienes
  作者：Liang Deng、Anthony J. Giessert、Oksana O. Gerlitz、Xing Dai、Steven T. Diver、Huw M. L. Davies

  DOI：10.1021/ja045173t

  日期：2005.2.1

  A two-step, three-component coupling of an alkyne, enol ether, and vinyl diazoester was accomplished by use of successive metal carbene-catalyzed transformations. This efficient approach to cycloheptadienes is both diastereo- and enantioselective. Kinetic resolution was accomplished on dienol ethers bearing a racemic chiral center at the propargylic position. A model is offered which explains the observed selectivity and accounts for the reactivity difference between trans- and cis-dienol ethers.
• Intermolecular Enol Ether−Alkyne Metathesis
  作者：Anthony J. Giessert、Lee Snyder、Jordan Markham、Steven T. Diver

  DOI：10.1021/ol034459k

  日期：2003.5.1

  [GRAPHICS]A new intermolecular metathesis between a variety of alkynes and alkyl enol ethers is described. The best results were obtained with the second generation Grubbs' precatalysts. The reaction occurred with a high degree of regioselectivity and provided electron-rich dienes, which underwent a variety of [4 + 2] cycloadditions.