Methyl 13(S)-<(1-methoxy-1-methylethyl)dioxy>-9(Z),11(E)-octadecadienoate | 132194-60-6

• 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 13(S)-<(1-methoxy-1-methylethyl)dioxy>-9(Z),11(E)-octadecadienoate
• 英文别名: Methyl 13(S)-[(1-methoxy-1-methylethyl)dioxy]-9(Z),11(E)-octadecadienoate；methyl (9Z,11E,13S)-13-(2-methoxypropan-2-ylperoxy)octadeca-9,11-dienoate
• CAS: 132194-60-6
• 化学式: C₂₃H₄₂O₅
• 分子量: 398.583
• InChiKey: DHMITAAAIPJVDB-IYQRKSMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  28.0
• 可旋转键数：
  18.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl 13(S)-<(1-methoxy-1-methylethyl)dioxy>-9(Z),11(E)-octadecadienoate 在 platinum on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 methyl 13-hydroperoxyoctadecanoic acid
  参考文献：
  名称：

  Chemoselective Hydrogenation of Unsaturated Peroxides

  摘要：

  Chemoselective hydrogenation of unsaturated monoperoxyketals provides new methodology for the synthesis of saturated and allyl hydroperoxides.

  DOI：

  10.1080/00397919508011807
• 作为产物：
  描述：

  13(S)--过氧羟基-9,11-十八碳二烯酸 在 4-甲基苯磺酸吡啶 作用下， 生成 Methyl 13(S)-<(1-methoxy-1-methylethyl)dioxy>-9(Z),11(E)-octadecadienoate
  参考文献：
  名称：

  通过脂氧合酶和脂酶的区域选择性，立体选择性合成氢过氧化二酰基甘油磷酸胆碱

  摘要：

  1-硬脂酰-2- [13' - （小号）-hydroperoxy-（9' Ž，11' ë）-octadecadienoyl] - SN -glycero -3-磷酸胆碱（11）通过任何区域选择性和没有污染合成立体-异构体通过脂氧合酶催化的过氧化，脂酶催化的硬脂酰化和二环己基碳二亚胺介导的（DCC）酯化反应的组合形成化学异构体。

  DOI：

  10.1039/c39900001281

文献信息

• Baba, N; Yoneda, K; Iwasa, J, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 824 - 827
  作者：Baba, N、Yoneda, K、Iwasa, J、Tahara, S、Kaneko, T、Matsuo, M

  DOI：——

  日期：——
• An organometallic approach to peroxy ketals
  作者：Patrick Dussault、Ayman Sahli、Thane Westermeyer

  DOI：10.1021/jo00072a032

  日期：1993.9

  A new method for peroxyketal synthesis is presented based upon formation of carbon-carbon bonds in the presence of a protected hydroperoxide. The 2-methoxypropyl perketal of 4(S)-hydroperoxy-2(E)-nonenal (2) undergoes reaction with a variety of metal hydrides and organometallic reagents to produce 4-peroxy 2-enols in good to excellent yields via chemoselective addition to the carbonyl carbon. Oxidation of the allylic alcohol to the 4-peroxy 2-enone is followed by deprotection to furnish a single enantiomer of a 4-hydroxyperoxy 2(E)-enone. Photochemical isomerization by the method of Snider induces spontaneous cyclization to epimeric 3-hydroxy-1,2-dioxins (hydroxy endoperoxides). Acidic methanolysis furnishes readily separable diastereomeric perketals as single enantiomers.
• A new synthon for optically active diene hydroperoxides
  作者：Patrick Dussault、In Quen Lee、Scott Kreifels

  DOI：10.1021/jo00013a001

  日期：1991.6

  The olefination of an enzymatically derived gamma-peroxy-alpha,beta-unsaturated aldehyde (1) allows the synthesis of optically active diene hydroperoxides in high enantiomeric excess. The application of this method to the synthesis of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid methyl ester is presented.
• BABA, NAOMICHI;YONEDA, KENJI;TAHARA, SHOICH;IWASA, JUNKICHI;KANEKO, TAKAO+, J. CHEM. SOC. CHEM. COMMUN.,(1990) N8, C. 1281-1282
  作者：BABA, NAOMICHI、YONEDA, KENJI、TAHARA, SHOICH、IWASA, JUNKICHI、KANEKO, TAKAO+

  DOI：——

  日期：——
• DUSSAULT, PATRICK;LEE, IN QUEN;KREIFELS, SCOTT, J. ORG. CHEM., 56,(1991) N3, C. 4087-4089
  作者：DUSSAULT, PATRICK、LEE, IN QUEN、KREIFELS, SCOTT

  DOI：——

  日期：——