(E)-9,10-epoxyoctadecanoic acid methyl ester

• 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: (E)-9,10-epoxyoctadecanoic acid methyl ester
• 英文别名: Methyl (E)-9,10-epoxyoctadecanoate；methyl trans-9,10-epoxyoctadecanoate；trans-methyl 8-(3-octyloxiran-2-yl)octanoate；methyl 8-(3-octyloxiran-2-yl)octanoate；(+/-)-threo-9,10-epoxy-octadecanoic acid methyl ester；(+/-)-threo-9,10-Epoxy-octadecansaeure-methylester；trans-9,10-Epoxy-stearinsaeure-methylester；methyl trans-9,10-epoxystearate；methyl oleate epoxide；trans-9,10-Epoxystearic acid methyl ester；methyl 8-[(2S,3S)-3-octyloxiran-2-yl]octanoate
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: CAMHHLOGFDZBBG-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-9,10-epoxyoctadecanoic acid methyl ester 在 氢氧化钾 作用下， 生成 外消旋反式-9,10-环氧硬脂酸
  参考文献：
  名称：

  Gunstone; Jacobsberg, 1972, vol. 9, p. 26,32

  摘要：

  DOI：
• 作为产物：
  描述：

  油酸甲酯 在 甲酸 、 双氧水 作用下， 反应 3.5h， 生成 (E)-9,10-epoxyoctadecanoic acid methyl ester
  参考文献：
  名称：

  环氧化物的催化开环：在生物增塑剂合成中的应用

  摘要：

  乙酸酐将一，二或三取代的环氧化物开环成相应的二乙酸酯，是由弱碱（如碳酸形式的水滑石）催化的。该反应在没有溶剂的情况下在423K下进行，并且在简单再生4次后以恒定转化率重复使用固体催化剂。油酸甲酯环氧化物的开环导致有用的二乙酸油酸甲酯的形成。 从植物油开始，在三个催化步骤（甲烷分解，环氧化然后开环）中制备聚乙酸酯衍生物。通过将这些产品与PVC混合来制备塑料溶胶，并评估其流变性。记录的数据表明它们可以充当生物增塑剂，其行为与邻苯二甲酸酯参考物相似。

  DOI：

  10.1016/j.apcata.2010.11.020

文献信息

• Synthesis and desaturation of monofluorinated fatty acids 1
  作者：Peter H. Buist、Kostas A. Alexopoulos、Behnaz Behrouzian、Brian Dawson、Bruce Black

  DOI：10.1039/a701571b

  日期：——

  A series of monofluoro C16 and C18 fatty acids have been synthesized and used as mechanistic probes for fatty acid desaturation. Only fluoroolefinic products are obtained when these compounds are processed by an in vivo Saccharomyces cerevisiae ω9 desaturating system as determined by 1H-decoupled 19F NMR and GC–MS analysis. No evidence for fluorohydrin formation has been found when either methyl (R,S)-9- or 10-fluoropalmitate (stearate) 3a,b and 5a,b was incubated with the ω9 desaturase. On desaturation α- and β-fluorine substituent effects (kH/kF) of magnitude 6.2 and 2.4, respectively, have been measured by direct competition experiments between 3a and 3b and between methyl 16-fluoropalmitate 3c and 3b. These results do not support the involvement of discrete hydroxylated and carbocationic intermediates in fatty acid desaturation. Substantial apparent steric effects have been observed for monofluorostearoyl substrates 5c–f bearing a fluorine distal from the site of initial oxidation. In the case of (R,S)-methyl 12-fluorostearate 5f, we show that both enantiomers are desaturated at comparable rates.

  一系列单氟代的C16和C18脂肪酸已被合成并作为机制探针用于脂肪酸脱饱和的研究。当这些化合物经过体内酿酒酵母ω9脱饱和系统处理后，根据1H去耦19F核磁共振和气相色谱-质谱分析，仅得到了含氟烯烃的产物。无论是甲基（R,S）-9-还是10-氟代棕榈酸（硬脂酸）3a,b和5a,b与ω9脱饱和酶共孵育时，均未发现形成氟醇的迹象。在脱饱和过程中，通过3a与3b以及甲基16-氟代棕榈酸3c与3b之间的直接竞争实验，分别测得α-和β-氟代取代基效应（kH/kF）大小为6.2和2.4。这些结果不支持脂肪酸脱饱和过程中涉及离散的羟基化和碳正离子中间体。对于远离初始氧化位点的氟代硬脂酰基底物5c–f，观察到了显著的表观立体效应。就（R,S）-甲基12-氟代硬脂酸5f而言，我们证明了两种对映体以相近速率进行脱饱和。
• PROCESS FOR FUNCTIONALIZATION OF UNSATURATED COMPOUNDS
  申请人：Casciato Stefano

  公开号：US20130211033A1

  公开（公告）日：2013-08-15

  The present invention relates to a process for synthesizing a multifunctional compound, including the reaction of a compound of formula (II) with atmospheric or molecular oxygen, in the presence of at least one aldehyde of formula (III), and optionally in the presence of at least one catalyst or at least one radical initiator; wherein: R 10 , R 20 , R 30 , R 40 , R 50 , L 2 , R 60 , R 7 , R 8 , and R 9 are as described in the claims. The invention also relates to the use of these compounds as monomers for the preparation of polyurethane. The invention also relates to the use of these compounds as monomers of polymers or of biopolymers.

  本发明涉及一种合成多功能化合物的方法，包括将式（II）的化合物与大气或分子氧在至少一种醛（式（III））的存在下反应，可选地在至少一种催化剂或至少一种自由基引发剂的存在下；其中：R10、R20、R30、R40、R50、L2、R60、R7、R8和R9如权利要求中所述。该发明还涉及将这些化合物用作聚氨酯制备中的单体的用途。该发明还涉及将这些化合物用作聚合物或生物聚合物的单体的用途。
• Cooperative catalyst system for the synthesis of oleochemical cyclic carbonates from CO₂and renewables
  作者：Nils Tenhumberg、Hendrik Büttner、Benjamin Schäffner、Daniela Kruse、Michael Blumenstein、Thomas Werner

  DOI：10.1039/c6gc00671j

  日期：——

  Taking Control! The binary catalyst system composed of MoO3 and an organic phoshponium salt [Bu4P]X proved very efficient to produce oleochemical cyclic carbonates from renewables.

  掌控一切！由MoO 3和有机磷鎓盐[Bu 4 P] X组成的二元催化剂体系经证明可非常有效地从可再生能源生产油化学环状碳酸酯。
• Synthesis of fatty ketoesters by tandem epoxidation–rearrangement with heterogeneous catalysis
  作者：Vicente Dorado、Lena Gil、José A. Mayoral、Clara I. Herrerías、José M. Fraile

  DOI：10.1039/c9cy01899a

  日期：——

  Fatty ketoesters are obtained from unsaturated fatty esters in a tandem two-step process with a combination of two heterogeneous catalysts, without intermediate purification and with maximum productivity of the catalysts through recycling and reuse.

  脂肪酮酯是从不饱和脂肪酯中通过串联两步过程获得的，使用两种异质催化剂的组合，无需中间纯化，通过循环再利用最大限度地提高催化剂的生产率。
• The fluorine gauche effect. Langmuir isotherms report the relative conformational stability of (±)-erythro- and (±)-threo-9,10-difluorostearic acidsElectronic supplementary information (ESI) available: characterisation of compounds 4, 5, 7–9, 11–13. See http://www.rsc.org/suppdata/cc/b2/b202891c/
  作者：Mustafa Tavasli、David O’Hagan、Christopher Pearson、Michael C. Petty

  DOI：10.1039/b202891c

  日期：2002.5.17

  (±)-Erythro- and (±)-threo- 9,10-difluorostearic acids, which differ only by a stereogenic interconversion of a single C–F bond, have significantly different conformational stabilities.

  (±)-红栓酸和(±)-白栓酸这两种9,10-二氟硬脂酸仅在一个C-F键的立体异构互变上有所不同，但它们的构象稳定性却有显著差异。