2,12-Bis-methoxycarbonyl-8-methylene-tridec-6-ynedioic acid dimethyl ester | 134149-24-9

• 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: 2,12-Bis-methoxycarbonyl-8-methylene-tridec-6-ynedioic acid dimethyl ester
• CAS: 134149-24-9
• 化学式: C₂₀H₂₈O₈
• 分子量: 396.438
• InChiKey: YPAGUXREQUWRFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  dimethyl 4-pentenylmalonate 在 Pd(dppe) 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到2,12-Bis-methoxycarbonyl-8-methylene-tridec-6-ynedioic acid dimethyl ester
  参考文献：
  名称：

  Formation de derives cyclopentaniques assistee par une espece hydrure de palladium : Aspects synthetiques et mecanisme

  摘要：

  In the presence of a palladium(0) complex and potassium t-butoxide, the acetylenic compounds 2 bearing in delta a nucleophilic functionality are smoothly transformed with excellent yields, either into 2,2-difunctionalized methylene cyclopentanes or into monofunctionalized 2-methylcyclopentenes. Each of these compounds can be specifically obtained depending on the choice of the experimental conditions.A set of diverse reactions involving mainly potassium hydride as the base showed clearly that HPdOtBu is not the active catalytic species which is mainly a sigma-ethynylpalladium hydride formed by the metal insertion in the acetylenic carbon hydrogen bond.

  DOI：

  10.1016/s0040-4020(01)89040-2

文献信息

• Cyclisation of ω-unsaturated β-dicarbonylcompounds catalyzed by a palladium hydride species
  作者：Nuno Monteiro、Geneviève Balme、Jacques Gore

  DOI：10.1016/s0040-4039(00)74294-8

  日期：1991.3

  When treated with potassium t-butoxide and then with a palladium(O) complex, the title compounds 1, 2, or 9 are smoothly cyclized by an attack of the enolates onto the unsaturation assisted by a palladium (II) species of tBuO-Pd-H type. The formation of a five-membered ring is particularly favored in such a process.