methyl (E)-9-hydroperoxyoctadec-10-enoate | 26770-47-8

• 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: methyl (E)-9-hydroperoxyoctadec-10-enoate
• 英文别名: methyl 10-hydroperoxyoctadec-8-enoate
• CAS: 26770-47-8
• 化学式: C₁₉H₃₆O₄
• 分子量: 328.492
• InChiKey: IBCITAFQTDFKGC-NTCAYCPXSA-N

物化性质

• 沸点：
  435.6±38.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-9-hydroperoxyoctadec-10-enoate 生成 (S)-methyl 9-hydroperoxyoctadec-10(E)-enoate
  参考文献：
  名称：

  外消旋氢过氧化物的拆分：光学纯氢过氧化物天然产物的制备

  摘要：

  Le meilleur resultat a ete obtenu en utilisant des ethers devinyle 制备partir du menthol et du (-)-trans-phenyl-2 cyclohexanol, pour synthetiser des peracetals 非对映异构体 avec les hydroperoxydes racemiques

  DOI：

  10.1021/ja00226a070
• 作为产物：
  描述：

  反-9-十八碳烯酸甲酯 生成 methyl (E)-9-hydroperoxyoctadec-10-enoate
  参考文献：
  名称：

  CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631

  摘要：

  DOI：

文献信息

• Bascetta, Emanuele; Gunstone, Frank D., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2207 - 2216
  作者：Bascetta, Emanuele、Gunstone, Frank D.

  DOI：——

  日期：——
• A Mechanistic Study of Oleate Autoxidation: Competing Peroxyl H-Atom Abstraction and Rearrangement
  作者：Ned A. Porter、Karen A. Mills、Randall L. Carter

  DOI：10.1021/ja00094a026

  日期：1994.7

  The mechanism of methyl oleate autoxidation was investigated. HPLC techniques were developed to analyze the products of autoxidation (hydroperoxides and the corresponding alcohols). The alcohols could be completely resolved by normal-phase chromatography, six products being characterized having oxygen substitution and double position as follows: 11-OOH-trans-Delta(9-10), 11-OOH-cis-Delta(9-10), 10-OOH-trans-Delta(8-9), 9-OOH-trans-Delta(10-11), 8-OOH-trans-Delta(9-10), 8-OOH-cis-Delta(9-10) As the hydrogen atom donor concentration of the medium of autoxidation is increased, increased 11-cis, 8-cis, 9-trans, and 10-trans hydroperoxides and decreased 11-trans and 8-trans hydroperoxides were obtained, consistent with a mechanism in which peroxyl H-atom abstraction and [2,3] allylperoxyl rearrangement are in competition. An iterative computer kinetic analysis was developed which modeled the oleate autoxidation mechanism, and rearrangement rate constants were determined. Allylperoxyl radicals undergo rearrangement with different rates depending on the geometry of the allylperoxyl.
• Frankel, Edwin N.; Garwood, Robert F.; Khambay, Bhupinder P. S., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2233 - 2240
  作者：Frankel, Edwin N.、Garwood, Robert F.、Khambay, Bhupinder P. S.、Moss, Gerard P.、Weedon, Basil C. L.

  DOI：——

  日期：——
• Porter Ned A., Mills Karen A., Caldwell Sarah E., Dubay George R., J. Amer. Chem. Soc, 116 (1994) N 15, S 6697-6705
  作者：Porter Ned A., Mills Karen A., Caldwell Sarah E., Dubay George R.

  DOI：——

  日期：——
• FRANKEL, E. N.;GARWOOD, R. F.;KHAMBAY, BHUPINDER, P. S.;MOSS, G. P.;WEEDO+, J. CHEM. SOC. PERKIN TRANS., 1984, N 10, 2233-2240
  作者：FRANKEL, E. N.、GARWOOD, R. F.、KHAMBAY, BHUPINDER, P. S.、MOSS, G. P.、WEEDO+

  DOI：——

  日期：——