ethyl (12Z)-10-hydroxy-9-nitro-12-octadecenoate

• 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 (12Z)-10-hydroxy-9-nitro-12-octadecenoate
• 英文别名: ethyl (Z)-10-hydroxy-9-nitrooctadec-12-enoate
• 化学式: C₂₀H₃₇NO₅
• 分子量: 371.517
• InChiKey: WYCIKXIJKMUIKC-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  亚油酸乙酯 在 硫酸 、 sodium nitrite 作用下， 以 环己烷 为溶剂， 生成 ethyl (12Z)-10-hydroxy-9-nitro-12-octadecenoate 、 ethyl (12Z)-9-hydroxy-10-nitro-12-octadecenoate 、 ethyl (9Z)-12-hydroxy-13-nitro-9-octadecenoate 、 ethyl (9Z)-13-hydroxy-12-nitro-9-octadecenoate
  参考文献：
  名称：

  Acid-Promoted Reactions of Ethyl Linoleate with Nitrite Ions:  Formation and Structural Characterization of Isomeric Nitroalkene, Nitrohydroxy, and Novel 3-Nitro-1,5-hexadiene and 1,5-Dinitro-1,3-pentadiene Products

  摘要：

  The reaction of ethyl linoleate (1) with NO2- in different air-equilibrated acidic media resulted in the formation of complex patterns of products, some of which could be isolated by repeated TLC fractionation and were formulated as the nitroalkenes 2-5, the novel (1E, 5Z)-3-nitro-1,5-hexadienes 6/7, the novel (E,E)-1,5-dinitro-1,3-pentadiene derivatives 8 and 9, and the nitro alcohols 10/11 and 12/13 by extensive GC-MS and 2D NMR analysis, as aided by 1D Hartmann-Hahn proton mapping experiments. Similar reaction of methyl oleate gave mainly nitroalkene (14/15) and allylic nitro derivatives (16/17). Formation of 2-13 may be envisaged in terms of HNO2-mediated nitration pathways in which regioisomeric beta-nitroalkyl radical intermediates derived from attack of NO2 to the 1,4-pentadiene moiety of 1 evolve through competitive H-atom abstraction and free radical combination routes.

  DOI：

  10.1021/jo000090q

文献信息

• Acid-Promoted Reactions of Ethyl Linoleate with Nitrite Ions:  Formation and Structural Characterization of Isomeric Nitroalkene, Nitrohydroxy, and Novel 3-Nitro-1,5-hexadiene and 1,5-Dinitro-1,3-pentadiene Products
  作者：Alessandra Napolitano、Emanuela Camera、Mauro Picardo、Marco d'Ischia

  DOI：10.1021/jo000090q

  日期：2000.8.1

  The reaction of ethyl linoleate (1) with NO2- in different air-equilibrated acidic media resulted in the formation of complex patterns of products, some of which could be isolated by repeated TLC fractionation and were formulated as the nitroalkenes 2-5, the novel (1E, 5Z)-3-nitro-1,5-hexadienes 6/7, the novel (E,E)-1,5-dinitro-1,3-pentadiene derivatives 8 and 9, and the nitro alcohols 10/11 and 12/13 by extensive GC-MS and 2D NMR analysis, as aided by 1D Hartmann-Hahn proton mapping experiments. Similar reaction of methyl oleate gave mainly nitroalkene (14/15) and allylic nitro derivatives (16/17). Formation of 2-13 may be envisaged in terms of HNO2-mediated nitration pathways in which regioisomeric beta-nitroalkyl radical intermediates derived from attack of NO2 to the 1,4-pentadiene moiety of 1 evolve through competitive H-atom abstraction and free radical combination routes.