methyl (E)-tetradec-7-enoate | 135982-43-3

• 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 (E)-tetradec-7-enoate
• 英文别名: (E)-methyl tetradec-7-enoate；7-Tetradecenoic acid, methyl ester
• CAS: 135982-43-3
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: IWXVCJGSCBUTCJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-tetradec-7-enoate 在 甲基磺酰胺 、 AD-mix-β 、 sodium sulfite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 115.5h， 以75%的产率得到methyl (R,R)-7,8-dihydroxytetradecanoate
  参考文献：
  名称：

  Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450BioI

  摘要：

  A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450(BioI). This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.027
• 作为产物：
  描述：

  (E)-2-(tetradec-7-en-1-yloxy)tetrahydro-2H-pyran 在 甲醇 、 Jones reagent 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 3.33h， 生成 methyl (E)-tetradec-7-enoate
  参考文献：
  名称：

  Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450BioI

  摘要：

  A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450(BioI). This mediates the biosynthesis of pimelic acid via C-C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.027

文献信息

• Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
  作者：D. M. Zubrytski、D. G. Kananovich、E. A. Matiushenkov

  DOI：10.1134/s107042801706001x

  日期：2017.6

  endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl

  的氧化裂解外-和内-烷基-和羟烷基取代的双环[ Ñ .1.0]的烷-1-醇与（乙酰氧基λ 3 -iodanyl）苯，得到相应的甲基烯酸酯只与Ë或Ž双键的构型。该反应被用作害虫昆虫信息素的立体异构纯组分合成的关键阶段：（E）-dodec-9-en-1-yl乙酸酯（欧洲松枝蛾Rhyacionia buoliana），（Z）-tetradec -11 -en-1-yl醋酸盐（欧洲橡木卷叶草Tortrix viridana）和（3 E，8 Z，11 Z）-十四烷基-3,8,11-三烯-1-基乙酸酯（番茄切叶机Tuta absoluta）。
• PRODUCTION OF COMMERCIAL BIODIESEL FROM GENETICALLY MODIFIED MICROORGANISMS
  申请人：LS9, Inc.

  公开号：EP2417244A1

  公开（公告）日：2012-02-15
• PRODUCTION OF FATTY ACID DERIVATIVES
  申请人：LS9, Inc.

  公开号：EP2417246A1

  公开（公告）日：2012-02-15
• COMPOSITIONS COMPRISING AND METHODS FOR PRODUCING BETA-HYDROXY FATTY ACID ESTERS
  申请人：Pandey Archana

  公开号：US20140215904A1

  公开（公告）日：2014-08-07

  Disclosed are fatty ester compositions comprising beta-hydroxy fatty esters, as well as methods for producing beta-hydroxy fatty esters, and recombinant microorganisms useful in methods of producing beta-hydroxy fatty esters
• [EN] PRODUCTION OF COMMERCIAL BIODIESEL FROM GENETICALLY MODIFIED MICROORGANISMS<br/>[FR] PRODUCTION DE BIODIESEL COMMERCIAL A PARTIR DE MICROORGANISMES GENETIQUEMENT MODIFIES
  申请人：LS9 INC

  公开号：WO2010118409A1

  公开（公告）日：2010-10-14

  The invention provides a fermentation and recovery process for the production of biodiesel of commercial grade quality according to commercial and environmental standards (e.g., ASTM ANP, or EPA trace elements and emissions standards), by fermentation of carbohydrates using a genetically modified microorganism. The process provides a direct route for the production of fatty esters, without the need for producing oils which are later chemically transesterified with the concomitant production of large quantities of glycerin and other undesirable side -products.