(E)-ethyl-5,5-dimethyloct-2-en-7-ynoate | 517893-66-2

• 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: (E)-ethyl-5,5-dimethyloct-2-en-7-ynoate
• 英文别名: ethyl (E)-5,5-dimethyloct-2-en-7-ynoate
• CAS: 517893-66-2
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: IGTUAPWWNPJFOF-BQYQJAHWSA-N

物化性质

• 沸点：
  257.1±33.0 °C(predicted)
• 密度：
  0.936±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl-5,5-dimethyloct-2-en-7-ynoate 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 、 乙腈 为溶剂， 以54%的产率得到7,7-dimethyl-4-(ethoxycarbonyl)bicyclo[3.3.0]oct-1-en-3-one
  参考文献：
  名称：

  Intramolecular Pauson−Khand Reactions of α,β-Unsaturated Esters and Related Electron-Deficient Olefins

  摘要：

  The intramolecular Pauson-Khand (PK) reaction of a variety of electron-poor enynes having an ester, cyano, or phosphonate group at the olefin terminus is described. Depending on the reaction conditions and substitution at the enyne, their dicobalthexacarbonyl complexes led preferentially to the exocyclic 1,3-diene or to the PK cyclopentenone product. In general, the 1,3-diene was obtained as the major product under N-oxide-promoted conditions, while the PK product was selectively formed in refluxing acetonitrile.

  DOI：

  10.1021/jo026828g
• 作为产物：
  描述：

  5,5-dimethyl-3-trifluoromethylsulfonyloxycyclohex-2-en-1-one 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 3.66h， 生成 (E)-ethyl-5,5-dimethyloct-2-en-7-ynoate
  参考文献：
  名称：

  Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination

  摘要：

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.

  DOI：

  10.1021/ol401839e