ethyl 3-(2-methoxy-5-methylbenzyl)-3-methyl-4-pentenoate | 1189021-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: ethyl 3-(2-methoxy-5-methylbenzyl)-3-methyl-4-pentenoate
• 英文别名: Ethyl 3-[(2-methoxy-5-methylphenyl)methyl]-3-methylpent-4-enoate
• CAS: 1189021-12-2
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: UWJORZOTWDZOKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-4-(2-methoxy-5-methylphenyl)-3-methyl-2-buten-1-ol 、 原乙酸三乙酯 在 丙酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 15.0h， 以61%的产率得到ethyl 3-(2-methoxy-5-methylbenzyl)-3-methyl-4-pentenoate
  参考文献：
  名称：

  The Synthesis of Velloziolide via Nicholas Reaction Based γ-Carbonyl Cations

  摘要：

  The total synthesis of the 9,11-seco-rosane diterpene velloziolide (1) has been accomplished by employing the Nicholas reaction chemistry of 2a as a gamma-carbonyl cation equivalent. An initial model Study demonstrated the utility of Nicholas reactions of 2 in the generation of 4-arylalkynoate Co(2)(CO)(6) complexes, and in conjunction with Gilman cuprate addition and Johnson-Claisen rearrangement chemistry, the preparation of a 3-methyl-3-vinyl-4-arylalkanoate model for velloziolide. The Nicholas reaction/gamma-carbonyl cation methodology was then employed twice in the total synthesis to incorporate onto 3,4-methylenedioxytoluene the 4-carbon unit that became the gem-dimethyltetralin portion of the velloziolide and, subsequently, to incorporate the gamma-arylalkanoate function of the epsilon-lactone.

  DOI：

  10.1021/jo901471b