2-Methyl-cyclopent-1-enecarboxylic acid tert-butyl ester | 110614-28-3

• 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: 2-Methyl-cyclopent-1-enecarboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-methylcyclopentene-1-carboxylate
• CAS: 110614-28-3
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: ZICATEANDDROGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-cyclopent-1-enecarboxylic acid tert-butyl ester 在 对甲苯磺酸 作用下， 以 环己烷 为溶剂， 反应 2.0h， 生成 (6ci,9ci)-2-甲基-1-环戊烯-1-羧酸
  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
• 作为产物：
  描述：

  2-acetyl-hept-6-ynoate de tertiobutyle 在 Pd(dppe) potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以172 mg的产率得到2-Methyl-cyclopent-1-enecarboxylic acid tert-butyl 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

• Mayr, Herbert; Brueggen, Uwe von der, Chemische Berichte, 1988, vol. 121, p. 339 - 346
  作者：Mayr, Herbert、Brueggen, Uwe von der

  DOI：——

  日期：——
• MAYR, HERBERT;VON, DER BRUGGEN UWE, CHEM. BER., 121,(1988) N 2, 339-345
  作者：MAYR, HERBERT、VON, DER BRUGGEN UWE

  DOI：——

  日期：——
• 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.