methyl 10-methoxystearate | 29647-24-3

• 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 10-methoxystearate
• 英文别名: methyl 10-methoxyoctadecanoate；Methyl-10-methoxy-stearate
• CAS: 29647-24-3
• 化学式: C₂₀H₄₀O₃
• 分子量: 328.536
• InChiKey: QBIIWKRXWVUFSU-UHFFFAOYSA-N

物化性质

• 沸点：
  388.3±15.0 °C(Predicted)
• 密度：
  0.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 油酸甲酯 在 aluminium(III) triflate 作用下， 反应 1.0h， 生成 methyl 9-methoxyoctadecanoate 、 methyl 10-methoxystearate
  参考文献：
  名称：

  金属三氟甲磺酸盐催化剂在麻疯树油与甲醇和高级醇的酯交换反应中的应用

  摘要：

  本文描述了金属三氟甲磺酸盐在脂肪酯（三油精，油酸甲酯，亚油酸甲酯），脂肪酸（油酸）以及麻风树油与甲醇的（反式）酯化中的应用的实验研究。以及高级醇（乙醇，正丙醇，异丙醇，异丁醇，叔丁醇）。评估了金属类型（scan，铋，铝，镧，铜，锌）和工艺条件对反应性能的影响。使用Al（OTf）3获得最高的转化率。三油精与甲醇的反应在165°C下进行1小时的转化率为99 mol％，主要产物为甲酯。此外，尽管在混合物中的分数小于20摩尔％，但观察到脂肪酸链中碳-碳双键的部分甲氧基化。所述反式-esterification反应还成功地使用高级醇，得到> 95％的转化为乙醇进行，Ñ丙醇，异丙醇和异丁醇，而叔丁醇不具有反应性。对于油酸与甲醇的反应，观察到定量酯化，碳-碳双键的部分甲氧基化以及少量内酯的形成。使用的Al的方法（OTF）3被成功所执行的反式JO的-esterification反应（2.1重量％的FFA含

  DOI：

  10.1007/s11746-013-2364-3

文献信息

• Neighboring methoxyl participation in the acid catalyzed methoxylation of methylene-interrupted fatty acids
  作者：Néstor M. Carballeira、Marı́a V. González、Mayra Pagán

  DOI：10.1016/s0009-3084(97)00062-5

  日期：1997.10

  The boron trifluoride-methanol derivatization of methyl 9,12-octadecadienoate was studied. This methylene-interrupted diene was reacted with 50% BF3-MeOH for 15 h at 0-5 degrees C and the four monomethoxy and two dimethoxy derivatives thus obtained were analyzed by gas chromatography-mass spectrometry. The only dimethoxy adducts observed were characterized as methyl 9,12-dimethoxyoctadecanoate and methyl 10,13-dimethoxyoctadecanoate. The complete regiospecificity observed in the formation of the dimethoxy adducts is best explained by a common O-methyltetrahydrofuranium ion as the only intermediate under these reaction conditions. (C) 1997 Elsevier Science Ireland Ltd.
• Methoxylation of methyl oleate in the presence of dealuminated Y faujasites in their protonic form
  作者：Clément Lansalot-Matras、Paul Lozano、Daniel Pioch、Annie Finiels、Claude Moreau、Sylvain Claude

  DOI：10.1007/s11746-006-5030-1

  日期：2006.8

  AbstractMethoxylation of methyl oleate into methyl methoxy stearate was carried out in a batch reactor at temperatures ranging from 150 to 190°C in the presence of dealuminated H‐Y faujasites as catalysts. In the presence of an excess of methanol, the H‐Y faujasite with a Si/Al ratio of 15 was shown to achieve the title reaction with a yield of methyl methoxy stearate that does not exceed 40% because of the parallel formation, at comparable rates, of methyl oleate isomers identified as methyl elaidate, methyl trans‐vaccenate, and methyl cis‐vaccenate. Isomerization reactions were confirmed to occur rapidly in an independent manner. FFA are also present in small amounts owing to the in situ dehydration of methanol and subsequent hydrolysis of the esters. Finally, starting from pure oleic acid leads to results similar to those obtained with methyl oleate as the starting material.