(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester | 90080-97-0

• 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: (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester
• 英文别名: methyl (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoate；methyl 13(S)-hydroxyoctadeca-9(Z),11(E),15(Z)-trienoate；methyl 13-hydroxylinolenate
• CAS: 90080-97-0
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: JMEPYUAUPCWTSQ-GOSIXVIOSA-N

物化性质

• 沸点：
  421.4±33.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  22.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以73%的产率得到(9Z,11E,13S,15Z)-13-羟基-9,11,15-十八碳三烯酸
  参考文献：
  名称：

  Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

  摘要：

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

  DOI：

  10.1016/s0040-4020(01)80454-3
• 作为产物：
  描述：

  methyl (9Z,11E,13S,15Z)-13-t-butyldimethylsilyloxyoctadeca-9,11,15-trienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以92%的产率得到(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

  摘要：

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

  DOI：

  10.1016/s0040-4020(01)80454-3

文献信息

• Production of Hydroxy Unsaturated Fatty Acids Using Crude Lipoxygenase Obtained from Infected Rice Plants
  作者：Tadahiro Kato、Tsutomu Watanabe、Toshifumi Hirukawa、Norihiro Tomita、Tsuneo Namai

  DOI：10.1246/bcsj.69.1663

  日期：1996.6

  In order to explore the oxidation mode of lipoxygenase (LOX) obtained from infected rice plants, typical unsaturated fatty acids (3—8) were treated with LOX and oxygen. It was observed that ω-10 and ω-6 positions of unsaturated fatty acids were oxidized predominantly in the cases of exotic ω-6 (4 and 5) and ω-3 (7 and 8) series, respectively. In the case of endogenous fatty acids (3 and 6), oxidation at ω-6 position predominated. All the allylic alcohols obtained by reduction of the oxidation products with NaBH4 possess S-configuration.

  为了探索从感染的水稻植物中获得的脂氧化酶（LOX）的氧化模式，通过LOX和氧气处理了典型的不饱和脂肪酸（3—8）。观察到在异源ω-6（4和5）和ω-3（7和8）系列的不饱和脂肪酸中，主要在ω-10和ω-6位发生氧化。而在内源性脂肪酸（3和6）的情况下，ω-6位的氧化占主导地位。通过用NaBH4还原氧化产物获得的所有烯丙醇均具有S构型。
• Regio- and Stereoselective Monoepoxidation of Dienes using Methyltrioxorhenium: Synthesis of Allylic Epoxides
  作者：Saroj Ranjan De、Ganesh Kumar、Jawahar L. Jat、Saritha Birudaraju、Biao Lu、Rajkumar Manne、Narender Puli、Adeniyi Michael Adebesin、John R. Falck

  DOI：10.1021/jo501958d

  日期：2014.11.7

  Methyltrioxorhenium (MTO) complexed with pyridine was shown to be a highly effective catalyst for the regioselective monoepoxidation of conjugated di- and trienes using 30% H2O2 at or below room temperature. The resultant allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures present in many bioactive natural products. The site of epoxidation

  与吡啶络合的甲基三氧铼 (MTO) 被证明是在室温或低于室温下使用 30% H 2 O 2对共轭二烯和三烯进行区域选择性单环氧化的高效催化剂。由此产生的烯丙基环氧化物和由它们衍生的三醇是通用的合成中间体以及存在于许多生物活性天然产物中的亚结构。环氧化位点取决于烯烃取代、烯烃几何形状（Z与E)，以及相邻碳原子上存在吸电子取代基。对于 1-酰基（甲硅烷基）氧基五-2,4-二烯，与 Sharpless、过酸和羟基化二烯的其他定向环氧化的相邻区域选择性特征相比，通常有利于远端烯烃的环氧化。
• Regio- and Enantioselective Catalytic Monoepoxidation of Conjugated Dienes: Synthesis of Chiral Allylic <i>cis</i>-Epoxides
  作者：Jawahar L. Jat、Saroj Ranjan De、Ganesh Kumar、Adeniyi Michael Adebesin、Shyam K. Gandham、John R. Falck

  DOI：10.1021/acs.orglett.5b00281

  日期：2015.2.20

  Ti(IV)-salan 4 catalyzes the diastereo- and enantioselective monoepoxidation of conjugated dienes using 30% H2O2 at rt or below even in the presence of other olefins and adjacent stereocenters. Its enantiomer, ent-4, provides access to the opposite diastereomer or enantiomer. The resultant chiral allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures

  即使在其他烯烃和相邻立构中心存在的情况下，Ti(IV)-salan 4在室温或更低温度下使用 30% H 2 O 2催化共轭二烯的非对映和对映选择性单环氧化。其对映体ent - 4可提供相反的非对映体或对映体。所得的手性烯丙环氧化物以及由它们衍生的三醇是多用途的合成中间体以及存在于许多生物活性天然产物中的子结构。环氧化对于Z-烯烃具有高度特异性。对于 1-酰基（甲硅烷基）氧基五-2,4-二烯，与 Sharpless、过酸和羟基化二烯的其他直接环氧化的相邻区域选择性特征相比，通常有利于远端烯烃的环氧化。