3-(1'-acetoxypentyl)-8-(1'-hydroxypropyl)-1,2,8,9-decatetraene | 1131881-32-7

• 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: 3-(1'-acetoxypentyl)-8-(1'-hydroxypropyl)-1,2,8,9-decatetraene
• CAS: 1131881-32-7
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: XCYOHIWDRNBCMR-UHFFFAOYSA-N

物化性质

• 沸点：
  441.5±45.0 °C(predicted)
• 密度：
  0.922±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1'-acetoxypentyl)-8-(1'-hydroxypropyl)-1,2,8,9-decatetraene 在 sodium iodide 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以80%的产率得到1-ethyl-4-methylene-5-(1'(E)-pentylidene)-1,3,4,5,6,7,8,9-octahydrocycloocta[c]furan
  参考文献：
  名称：

  An Efficient Synthesis of 2,5-Dihydrofuran-Fused Bicyclic Skeletons via the Pd(II)-Catalyzed Tandem-Cyclization Reaction of 1,ω-Bisallenols

  摘要：

  A palladium(II)-catalyzed tandem double-cyclization reaction of 1,omega-bisallenols was developed to form 2,5-dihydrofuran-fused bicyclic skeletons. With "unsymmetric" substrates, the reaction may also be realized with one hydroxyl group being protected as the acetate. Optically active bicyclic products were prepared by applying the Novozym-435 catalyzed kinetic resolution and the tandem double cyclization of these optically active allenol-allenyl acetates. The reaction may proceed via an oxypalladation, insertion, and elimination process.

  DOI：

  10.1021/ol802794t
• 作为产物：
  描述：

  3-(7'-iodo-5'-heptynyl)octa-1,2-dien-4-yl acetate 、 丙醛 在 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以75%的产率得到3-(1'-acetoxypentyl)-8-(1'-hydroxypropyl)-1,2,8,9-decatetraene
  参考文献：
  名称：

  An Efficient Synthesis of 2,5-Dihydrofuran-Fused Bicyclic Skeletons via the Pd(II)-Catalyzed Tandem-Cyclization Reaction of 1,ω-Bisallenols

  摘要：

  A palladium(II)-catalyzed tandem double-cyclization reaction of 1,omega-bisallenols was developed to form 2,5-dihydrofuran-fused bicyclic skeletons. With "unsymmetric" substrates, the reaction may also be realized with one hydroxyl group being protected as the acetate. Optically active bicyclic products were prepared by applying the Novozym-435 catalyzed kinetic resolution and the tandem double cyclization of these optically active allenol-allenyl acetates. The reaction may proceed via an oxypalladation, insertion, and elimination process.

  DOI：

  10.1021/ol802794t

文献信息

• An Efficient Synthesis of 2,5-Dihydrofuran-Fused Bicyclic Skeletons via the Pd(II)-Catalyzed Tandem-Cyclization Reaction of 1,ω-Bisallenols
  作者：Youqian Deng、Yunlong Shi、Shengming Ma

  DOI：10.1021/ol802794t

  日期：2009.3.19

  A palladium(II)-catalyzed tandem double-cyclization reaction of 1,omega-bisallenols was developed to form 2,5-dihydrofuran-fused bicyclic skeletons. With "unsymmetric" substrates, the reaction may also be realized with one hydroxyl group being protected as the acetate. Optically active bicyclic products were prepared by applying the Novozym-435 catalyzed kinetic resolution and the tandem double cyclization of these optically active allenol-allenyl acetates. The reaction may proceed via an oxypalladation, insertion, and elimination process.