(E)-Ethyl 3-ethyl-4-methyl-2,4-pentadienoate | 136707-80-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-Ethyl 3-ethyl-4-methyl-2,4-pentadienoate
• 英文别名: ethyl (2E)-3-ethyl-4-methylpenta-2,4-dienoate
• CAS: 136707-80-7
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: SNQLEAMDQMEKQG-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2E)-2-methyl-2-penten-1-ol 、 1-(phenylsulfinyl)-2,2,2-triethoxyethane 在 2,4,6-三甲基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到(E)-Ethyl 3-ethyl-4-methyl-2,4-pentadienoate
  参考文献：
  名称：

  One-flask, regiospecific conversions of allylic alcohols into 2-carbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoester

  摘要：

  Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100-degrees-C sequentially via a [3,3] sigmatropic rearrangement and then a beta-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45-95% yields. This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific gamma-attachment of a two-carbon (ethoxycarbonyl)methylene unit via the synthetic equivalent of an S(N)2' process. Two examples are given in which rationally designed dienoates 20 and 24, prepared via this one-flask process and carrying a pendant alkene unit, undergo intramolecular 2 + 4 cycloaddition producing bicyclic cyclohexenes 21 and 25.

  DOI：

  10.1021/jo00025a008

文献信息

• One-flask, regiospecific conversions of allylic alcohols into 2-carbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoester
  作者：Gary H. Posner、R. David Crouch、Chris M. Kinter、Jean Christophe Carry

  DOI：10.1021/jo00025a008

  日期：1991.12

  Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100-degrees-C sequentially via a [3,3] sigmatropic rearrangement and then a beta-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45-95% yields. This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific gamma-attachment of a two-carbon (ethoxycarbonyl)methylene unit via the synthetic equivalent of an S(N)2' process. Two examples are given in which rationally designed dienoates 20 and 24, prepared via this one-flask process and carrying a pendant alkene unit, undergo intramolecular 2 + 4 cycloaddition producing bicyclic cyclohexenes 21 and 25.