E/Z acetic acid 4-ethoxy-2-methylene-1-phenylbut-3-enyl ester | 549504-72-5

• 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 acetic acid 4-ethoxy-2-methylene-1-phenylbut-3-enyl ester
• CAS: 549504-72-5
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: UTHCVIOBZAFSLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (E)-methyl 2-diazo-4-phenylbut-3-enoate 、 E/Z acetic acid 4-ethoxy-2-methylene-1-phenylbut-3-enyl ester 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 作用下， 以 正己烷 为溶剂， 反应 0.5h， 生成 (3S,4S,6S)-(acetoxy-phenylmethyl)-4-ethoxy-3-phenylcyclohepta-1,5-diene carboxylic acid methyl ester
  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
• 作为产物：
  描述：

  1-phenylprop-2-ynyl acetate 、 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99%的产率得到E/Z acetic acid 4-ethoxy-2-methylene-1-phenylbut-3-enyl ester
  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