allyl Δ²-cyclooctenyl ether | 105598-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl Δ²-cyclooctenyl ether
• 英文别名: (1Z)-3-prop-2-enoxycyclooctene
• CAS: 105598-44-5
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: VVQJUFLKMUCOAQ-VURMDHGXSA-N

物化性质

• 沸点：
  233.9±19.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  allyl Δ²-cyclooctenyl ether 在 Grubbs catalyst first generation 、 乙烯 作用下， 以 二氯甲烷 为溶剂， 22.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 以89%的产率得到2-(6-heptenyl)-2,5-dihydrofuran
  参考文献：
  名称：

  Zr-Catalyzed Kinetic Resolution of Aliphatic Cyclic Allylic Ethers. Carbocycles to Heterocycles by Ru- and Mo-Catalyzed Ring-Opening and Ring-Closing Metathesis

  摘要：

  The Zr-catalyzed kinetic resolution of aliphatic allylic ethers derived from five-, six-, seven-, and eight-membered ring allylic alcohols is reported. The level of resolution efficiency varies as a function of ring size and substitution pattern of the pendant alkene. The metal-catalyzed transformation of the above unsaturated ethers to dihydrofurans is also disclosed. Seven- and eight-membered ring substrates are readily converted to furans; in the presence of 10 mol % Ru catalyst 16. In contrast, the less reactive cyclopentenol systems demand the more potent Mo-based metathesis catalyst 3. The selectivity and reactivity patterns in the Zr-catalyzed process and the Ru- or Mo-catalyzed reactions differ from the previously reported reactions of the related styrenyl ethers.

  DOI：

  10.1021/jo991323k
• 作为产物：
  描述：

  (Z)-2-cycloocten-1-ol 、 3-溴丙烯 在 六甲基磷酰三胺 、 sodium hydride 作用下， 生成 allyl Δ²-cyclooctenyl ether
  参考文献：
  名称：

  Copper(I) catalysis of olefin photoreactions. 15. Synthesis of cyclobutanated butyrolactones via copper(I)-catalyzed intermolecular photocycloadditions of homoallyl vinyl or diallyl ethers

  摘要：

  DOI：

  10.1021/jo00377a015

文献信息

• Copper(I) catalysis of olefin photoreactions. 15. Synthesis of cyclobutanated butyrolactones via copper(I)-catalyzed intermolecular photocycloadditions of homoallyl vinyl or diallyl ethers
  作者：Subrata Ghosh、Swadesh R. Raychaudhuri、Robert G. Salomon

  DOI：10.1021/jo00377a015

  日期：1987.1
• Zr-Catalyzed Kinetic Resolution of Aliphatic Cyclic Allylic Ethers. Carbocycles to Heterocycles by Ru- and Mo-Catalyzed Ring-Opening and Ring-Closing Metathesis
  作者：Jeffrey A. Adams、J. Gair Ford、Paul J. Stamatos、Amir H. Hoveyda

  DOI：10.1021/jo991323k

  日期：1999.12.1

  The Zr-catalyzed kinetic resolution of aliphatic allylic ethers derived from five-, six-, seven-, and eight-membered ring allylic alcohols is reported. The level of resolution efficiency varies as a function of ring size and substitution pattern of the pendant alkene. The metal-catalyzed transformation of the above unsaturated ethers to dihydrofurans is also disclosed. Seven- and eight-membered ring substrates are readily converted to furans; in the presence of 10 mol % Ru catalyst 16. In contrast, the less reactive cyclopentenol systems demand the more potent Mo-based metathesis catalyst 3. The selectivity and reactivity patterns in the Zr-catalyzed process and the Ru- or Mo-catalyzed reactions differ from the previously reported reactions of the related styrenyl ethers.