cis-12,13-epoxy-cis-9-octadecenol

• 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: cis-12,13-epoxy-cis-9-octadecenol
• 英文别名: vernanol；(Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-en-1-ol
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: HLSBTIZMXCORIC-UKBCLVJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-12,13-epoxy-cis-9-octadecenol 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 13-hydroxy-cis-10-nonadecyl amine
  参考文献：
  名称：

  13（14）-羟基-顺式-10-壬二烯胺盐酸盐的合成

  摘要：

  AbstractCompatibility between a hydrophilic nanoclay reinforcement and organophilic polymer matrix resin is achieved by ion exchange reaction substitution of intra gallery mono‐ or divalent cation with foreign aliphatic long‐chain cation. The exchange of long‐chain cation increases the organophilicity of the clay layers and provides sufficient layer separation for polymer chains to impregnate into the formation of a nanocomposite. This study demonstrates the synthesis of hydroxy functional longchain amine hydrochloride from Vernonia galamensis oil (VO). Vernonia galamensis oil, containing a naturally epoxidized long‐chain TG, was transesterified under basic conditions to yield VO methyl esters (VOMe). The VOMe were reduced using lithium aluminum hydride (LAH) in hexane to obtain cis‐12,13‐epoxy‐cis‐9‐octadecenol (vernanol) as the primary product. Vernanol was then converted to vernanyl mesylate, followed by reaction with potassium cyanide to obtain cis‐13,14‐epoxy‐cis‐10‐nonadecenitrile (C19 nitrile). The C19 nitrile was reduced with LAH in diethyl ether medium and later reacted with hydrochloric acid to obtain the title product. 1H and 13C NMR, FTIR, and matrixassisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOFMS) techniques were used to characterize the intermediates and the title product.

  DOI：

  10.1007/s11746-003-0728-7

文献信息

• Synthesis of Sodium (+)-(12S,13R)-Epoxy-cis-9-octadecenyl Sulfonate from Vernonia Oil
  作者：Darryl C. Sutton、Nikki S. Johnson、Caswell Hlongwane、Folahan O. Ayorinde

  DOI：10.1007/s11746-009-1377-4

  日期：2009.7

  synthesized from vernonia oil (VO) by a series of simple reactions that include transesterification, metal hydride reduction, tosylation, and SN2 reactions. Conversion of VO into vernonia oil methyl esters (VOME) using sodium methoxide was quantitative. Subsequent reduction of VOME with lithium aluminum hydride yielded (+)‐(12S,13R)‐epoxy‐cis‐9‐octadecenol (94%), along with minor amounts of hexadecenol, octadecenol

  通过一系列简单的反应，从vernonia油（VO）合成了一种水溶性的发泡环氧烯烃磺酸钠（+）-（12 S，13 R）-环氧-顺式-9-十八碳烯基磺酸钠氢化物还原，甲苯磺酸化和S N 2反应。使用甲醇钠将VO转化为紫罗兰油甲酯（VOME）是定量的。随后的还原VOME的用氢化铝锂，得到（+） - （12小号，13 - [R ）-环氧顺-9-十八烯醇（94％），以及少量的hexadecenol，十八烯醇，沿顺-9-十八烯醇，和顺-9,12-十八烷二烯醇。（+）-（12秒将，13 R）-环氧顺式-9-十八碳烯醇与对甲苯磺酰氯甲苯磺酸化，以96％的收率得到（+）-（12 S，13 R）-环氧顺式-9-十八碳烯基甲苯磺酸酯。用碘化钠对甲苯磺酸盐进行碘化，然后与亚硫酸钠进行S N 2反应，得到（+）-（12 S，13 R）-环氧-顺式-9-十八碳烯基磺酸盐（63％收率）。这项研究证明了在不破坏（+）-（12
• Synthesis of 13(14)-hydroxy-<i>cis</i> -10-nonadecenyl amine hydrochloride
  作者：S. Balakrishnan、D. Raghavan

  DOI：10.1007/s11746-003-0728-7

  日期：2003.5

  AbstractCompatibility between a hydrophilic nanoclay reinforcement and organophilic polymer matrix resin is achieved by ion exchange reaction substitution of intra gallery mono‐ or divalent cation with foreign aliphatic long‐chain cation. The exchange of long‐chain cation increases the organophilicity of the clay layers and provides sufficient layer separation for polymer chains to impregnate into the formation of a nanocomposite. This study demonstrates the synthesis of hydroxy functional longchain amine hydrochloride from Vernonia galamensis oil (VO). Vernonia galamensis oil, containing a naturally epoxidized long‐chain TG, was transesterified under basic conditions to yield VO methyl esters (VOMe). The VOMe were reduced using lithium aluminum hydride (LAH) in hexane to obtain cis‐12,13‐epoxy‐cis‐9‐octadecenol (vernanol) as the primary product. Vernanol was then converted to vernanyl mesylate, followed by reaction with potassium cyanide to obtain cis‐13,14‐epoxy‐cis‐10‐nonadecenitrile (C19 nitrile). The C19 nitrile was reduced with LAH in diethyl ether medium and later reacted with hydrochloric acid to obtain the title product. 1H and 13C NMR, FTIR, and matrixassisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOFMS) techniques were used to characterize the intermediates and the title product.