ethyl 1-(5-(5,5-dimethylcyclopent-1-enyl)pent-4-ynyl)-2-oxocyclohexanecarboxylate | 1040475-48-6

• 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: ethyl 1-(5-(5,5-dimethylcyclopent-1-enyl)pent-4-ynyl)-2-oxocyclohexanecarboxylate
• CAS: 1040475-48-6
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: GWGBLBBCYHAOIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-(5-(5,5-dimethylcyclopent-1-enyl)pent-4-ynyl)-2-oxocyclohexanecarboxylate 在 gold(III) chloride 、 silver hexafluoroantimonate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以75%的产率得到ethyl-7,7-dimethyl-8-oxo-2,3,4,5,6,7,8,8a,9,10,11,11a-dodecahydro-1H-pentaleno[2,1-j]naphthalene-11a-carboxylate
  参考文献：
  名称：

  Gold-Catalyzed Synthesis of Polycyclic Enones from Carbon Tethered 1,3-Enynyl Carbonyls via Tandem Heteroenyne Metathesis and Nazarov Reaction

  摘要：

  An efficient and general Au(III)-catalyzed tandem reaction, heteroenyne metathesis and Nazarov cyclization, of 1,3-enynyl ketones to produce fused tri- and tetracyclic enones has been developed. The products were formed with excellent regioselectivity of the double bond position and with very high diastereoselectivities. In this reaction, the Au(III) catalyst exhibits dual roles for activating both alkynes and carbonyls.

  DOI：

  10.1021/ol801265s
• 作为产物：
  描述：

  1-(5-iodopent-1-yn-1-yl)-5,5-dimethylcyclopent-1-ene 、 2-环己酮甲酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以80%的产率得到ethyl 1-(5-(5,5-dimethylcyclopent-1-enyl)pent-4-ynyl)-2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  Gold-Catalyzed Synthesis of Polycyclic Enones from Carbon Tethered 1,3-Enynyl Carbonyls via Tandem Heteroenyne Metathesis and Nazarov Reaction

  摘要：

  An efficient and general Au(III)-catalyzed tandem reaction, heteroenyne metathesis and Nazarov cyclization, of 1,3-enynyl ketones to produce fused tri- and tetracyclic enones has been developed. The products were formed with excellent regioselectivity of the double bond position and with very high diastereoselectivities. In this reaction, the Au(III) catalyst exhibits dual roles for activating both alkynes and carbonyls.

  DOI：

  10.1021/ol801265s