(E)-dimethyl 5-ethylidenecyclohex-3-ene-1,1-dicarboxylate | 1380875-94-4

• 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: (E)-dimethyl 5-ethylidenecyclohex-3-ene-1,1-dicarboxylate
• CAS: 1380875-94-4
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: AJNGBKHCZGDMBB-WTKPLQERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  diethyl octa-1-ene-7-yne-5,5-dicarboxylate 在 1.2 molpercent gold nanoparticles supported on TiO₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 (E)-dimethyl 5-ethylidenecyclohex-3-ene-1,1-dicarboxylate 、 (Z)-dimethyl 5-ethylidenecyclohex-3-ene-1,1-dicarboxylate 、 dimethyl 3-{(E)-prop-1-enyl}cyclopent-3-ene-1,1-dicarboxylate 、 (Z)-dimethyl 3-(prop-1-en-1-yl)cyclopent-3-ene-1,1-dicarboxylate
  参考文献：
  名称：

  Cyclization of 1,6-Enynes Catalyzed by Gold Nanoparticles Supported on TiO₂: Significant Changes in Selectivity and Mechanism, as Compared to Homogeneous Au-Catalysis

  摘要：

  Gold nanoparticles supported on TiO2 (1.2 mol %) catalyze, for the first time under heterogeneous conditions, the cycloisomerization of a series of 1,6-enynes in high yields. In several cases, the product selectivity differs significantly as compared to homogeneous Au(I)-catalysis. Based on product analysis and stereoisotopic studies it is proposed that the major or exclusive pathway involves a 5-exo cyclization mode to form stereoselectively gold cyclopropyl carbenes that undergo a single cleavage pathway, in contrast to homogeneous Au-catalysis where the double cleavage pathway operates substantially.

  DOI：

  10.1021/ol301212j