(E/Z)-1-ethoxy-4-methyl-3-methylenepent-1-ene | 26643-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E/Z)-1-ethoxy-4-methyl-3-methylenepent-1-ene
• 英文别名: (E/Z)-1-ethoxy-3-isopropylbuta-1,3-diene；1-ethoxy-3-isopropyl-buta-1,3-diene；1-ethoxy-4-methyl-3-methylidenepent-1-ene
• CAS: 26643-38-9
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: AZVAXZICKHOKLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E/Z)-1-ethoxy-4-methyl-3-methylenepent-1-ene 、 methyl 2-(4-bromophenyl)-2-diazoacetate 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 、 (1R,2R)-1-(4-bromophenyl)-2-(2-ethoxyvinyl)-2-isopropylcyclopropane 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：

  3-甲基-1-丁炔 、 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83%的产率得到(E/Z)-1-ethoxy-4-methyl-3-methylenepent-1-ene
  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