2-((E)-hept-2-ynylidene)-1,1-bis(methoxycarbonyl)cyclopentane | 138769-99-0

• 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-((E)-hept-2-ynylidene)-1,1-bis(methoxycarbonyl)cyclopentane
• 英文别名: dimethyl (2E)-2-hept-2-ynylidenecyclopentane-1,1-dicarboxylate
• CAS: 138769-99-0
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: ZIEKVXSKFGDZTD-JLHYYAGUSA-N

物化性质

• 沸点：
  350.0±42.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-bromohexyne 、 dimethyl 4-pentenylmalonate 在 Pd(0)n potassium tert-butylate 、 potassium bromide 作用下， 生成 2-((E)-hept-2-ynylidene)-1,1-bis(methoxycarbonyl)cyclopentane
  参考文献：
  名称：

  Easy access to 5-(E)-alkynylidene tetrahydro-2 furanones by a palladium catalyzed process

  摘要：

  Biologically active ynenol lactones 1 are stereospecifically obtained when gamma-acetylenic carboxylates are reacted with 1-bromo 1-alkynes in the presence of a palladium(0)-phosphine complex. The reaction is effective only with the potassium carboxylate and the nature of the phosphine is essential for the cyclisation process.

  DOI：

  10.1016/s0040-4039(00)78865-4

文献信息

• Synthesis of ethynylidene cyclopentanes by a cyclisation catalyzed by the simultaneous presence of palladium (0) and copper (I)
  作者：Didier Bouyssi、Geneviève Balme、Jacques Gore

  DOI：10.1016/0040-4039(91)80215-r

  日期：1991.11

  Ethynylidene cyclopentanes can be formed in 35–71% yield from the reaction of the enolates of compounds such as δ-acetylenic malonates with 1-halogeno-1-alkynes. This reaction requires catalysis by both palladium (0) and copper (I) species.

  乙炔基丙二酸酯等化合物的烯醇化物与1-卤代-1-炔烃的反应可形成亚乙基环戊烷，产率为35-71％。该反应需要钯（0）和铜（I）物种的催化。
• An X⁻ (X = I, Br)-Triggered Ring-Opening Cyclization of Cyclopropenyl-Substituted Alkyl Halides or Mesylates: An Efficient and Highly Regio- and Stereoselective Approach to (<i>E)</i>-Haloalkylidene 4−7-Membered Cyclic Compounds
  作者：Jie Chen、Shengming Ma

  DOI：10.1021/jo900389m

  日期：2009.8.7

  Polyfunctionalized (E)-haloalkylidene cyclic products were efficiently synthesized in moderate to excellent yields via a regio- and stereoselective X- (X = I or Br)-triggered ring-opening intramolecular trapping of cyclopropenes 1. The reaction can be used for construction of 4-7-membered products. The E-stereoselectivity of the exo-C=C bond is very high. The carbon-halogen bond in the exo-C=C bond may further be elaborated to prepare differently substituted cyclic products with a stereodefined C=C bond.