tetramethyl 2,2'-(ethane-1,2-diylidene)(2E,2'E)-bis(cyclopentane-1,1-dicarboxylate) | 146445-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tetramethyl 2,2'-(ethane-1,2-diylidene)(2E,2'E)-bis(cyclopentane-1,1-dicarboxylate)
• CAS: 146445-33-2
• 化学式: C₂₀H₂₆O₈
• 分子量: 394.422
• InChiKey: GOVHJOZIZHOTDM-UTLPMFLDSA-N

物化性质

• 沸点：
  443.8±45.0 °C(predicted)
• 密度：
  1.325±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• 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 18-冠醚-6 、 Pd(dppe) 、 potassium hydride 作用下， 生成 1,1-dimethoxycarbonyl-2-methylene cyclopentane 、 tetramethyl 2,2'-(ethane-1,2-diylidene)(2E,2'E)-bis(cyclopentane-1,1-dicarboxylate)
  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

• Formation de derives cyclopentaniques assistee par une espece hydrure de palladium : Aspects synthetiques et mecanisme
  作者：Nuno Monteiro、Jacques Gore、Geneviève Balme

  DOI：10.1016/s0040-4020(01)89040-2

  日期：——

  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.