1-nonylbut-3-enyl acrylate | 949171-50-0

• 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: 1-nonylbut-3-enyl acrylate
• 英文别名: Tridec-1-en-4-yl prop-2-enoate
• CAS: 949171-50-0
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: RDQDKGSRANDFAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  1-nonylbut-3-enyl acrylate 在 Ru=CH-Ph(PCy₃)2Cl₂ 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以62%的产率得到6-nonyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor

  摘要：

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.

  DOI：

  10.1021/jo070600h
• 作为产物：
  描述：

  癸醛 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-nonylbut-3-enyl acrylate
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor

  摘要：

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.

  DOI：

  10.1021/jo070600h