methyl (E)-10-cyano-9-decenoate | 173602-43-2

• 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)-10-cyano-9-decenoate
• 英文别名: methyl 10-cyanoundec-10-enoate；methyl (E)-10-cyanodec-9-enoate
• CAS: 173602-43-2
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: DXIILQJKEIHJIN-VQHVLOKHSA-N

物化性质

• 沸点：
  314.2±25.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-十八碳烯二酸 在 Hoveyda-Grubbs catalyst second generation 、 硫酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 methyl (Z)-10-cyano-9-decenoate 、 methyl (E)-10-cyano-9-decenoate
  参考文献：
  名称：

  钌-亚烷基催化的交叉-复分解 的 脂肪酸 具有的导数 丙烯腈 和 丙烯酸甲酯：迈向长链双功能的关键一步 氨基酸 化合物

  摘要：

  这 钌 催化交叉复分解 的 脂肪的--酯类 来自植物油的 丙烯腈被表达。结果线性腈 酯产品具有潜在的新中间体 聚酰胺纤维合成。一系列可商购的催化剂 能够促进变革 10-十一碳烯酸甲酯 1，octadec-9-en-1,18-diate的二甲基 5和甲基蓖麻油酸酯9与丙烯腈 和基于缓慢添加的协议 催化剂 允许交叉使用的TON高达1900（92％的收益）复分解 和 丙烯腈。这些交叉复分解 条件已应用于 丙烯酸甲酯 TON达到7600。

  DOI：

  10.1039/c1gc15569e

文献信息

• METHOD FOR THE SYNTHESIS OF OMEGA-AMINO-ALKANOIC ACIDS
  申请人：Dubois Jean-Luc

  公开号：US20100168453A1

  公开（公告）日：2010-07-01

  The invention relates to a method for the synthesis of amino acids/esters of general formula NH 2 —(CH 2 ) n —COOR in which n is an integer between 5 and 14, and R is either H or an alkyl radical including from 1 to 4 carbon atoms, from natural long-chain mono-unsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule, said method comprising: first converting, if necessary, said natural long-chain fatty acid or ester into a monounsaturated fatty acid/ester of general formula R 1 —(CH 2 ) m —CH═CH—(CH 2 ) p —COOR in which R 1 is H, CH 3 or a COOR radical, m is an integer between 0 and 14 and p is an integer between 2 and 11, then submitting the latter to a crossed catalytic metathesis reaction with a compound of formula R 2 —CH═CH—R 3 in which R 2 is either H or CN and R 3 is CN or CH 2 NH 2 , provided that if R 2 is CN, R 3 can be only CN, and finally converting the resulting product of the general formula R 3 —CH═CH—(CH 2 ) p —COOR into an amino-acid, either by hydrogenation, or by hydrogenation of the triple terminal bond, or by amination of the double terminal bond.

  本发明涉及一种合成通式为NH2—(CH2)n—COOR的氨基酸/酯的方法，其中n为5至14之间的整数，R为H或包括1至4个碳原子的烷基基团，所述方法包括：首先，如果必要，将天然长链脂肪酸或酯转化为通式为R1—( )m—CH═CH—( )p—COOR的单不饱和脂肪酸/酯，其中R1为H，CH3或COOR基团，m为0至14之间的整数，p为2至11之间的整数；然后，将后者与通式为R2—CH═CH—R3的化合物进行交叉催化复分解反应，其中R2为H或CN，R3为CN或 NH2，如果R2为CN，则R3只能为CN；最后，将得到的通式为R3—CH═CH—( )p—COOR的产品转化为氨基酸，可以通过氢化，或通过氢化末端的三键，或通过末端的双键的氨基化来实现。
• [EN] USE OF RUTHENIUM COMPLEXES IN OLEFIN METATHESIS REACTION<br/>[FR] UTILISATION DE COMPLEXES DE RUTHÉNIUM DANS UNE RÉACTION DE MÉTATHÈSE D'OLÉFINES
  申请人：APEIRON SYNTHESIS SA

  公开号：WO2018087678A1

  公开（公告）日：2018-05-17

  The invention relates to the use of ruthenium complexes, which are homogeneous catalysts and/or precatalysts of the olefin metathesis reaction, which lead to the production of alkenes containing an internal (non-terminal) double C=C bond.

  该发明涉及使用钌配合物，这些配合物是烯烃转化反应的均相催化剂和/或前催化剂，从而导致产生含有内部（非末端）双键C=C的烯烃。
• [EN] CROSS METATHESIS APPROACH TO C11-C13 FATTY-CHAIN AMINO ESTERS FORM OLEIC ACID DERIVATIVES<br/>[FR] APPROCHE DE MÉTATHÈSE CROISÉE POUR AMINOESTERS À CHAÎNE GRASSE EN C11-C13 À PARTIR DE DÉRIVÉS DE L'ACIDE OLÉIQUE
  申请人：UNIV TOLEDO

  公开号：WO2015200200A1

  公开（公告）日：2015-12-30

  A concise method of producing nylon 11, 12, or 13 precursors from oleic acid or an ester of oleic acid is described. The method involves cross-metathesis reactions as the key C-C bond formation step. Subsequent steps are provided to convert the metathesis product to the corresponding nylon precursors. Also provided are the products of the method.

  描述了一种从油酸或油酸酯制备尼龙11、12或13前体的简明方法。该方法涉及交叉烯烃酰胺反应作为关键的C-C键形成步骤。提供了将烯烃酰胺产物转化为相应尼龙前体的后续步骤。还提供了该方法的产物。
• CROSS METATHESIS PROCESS
  申请人：ARKEMA FRANCE

  公开号：US20150353479A1

  公开（公告）日：2015-12-10

  A process for the synthesis of an unsaturated product by cross metathesis between a first unsaturated compound having at least 8 carbon atoms and a second unsaturated compound having less than 8 carbon atoms, including: feeding a reactor with the first unsaturated compound, the second unsaturated compound and a metathesis catalyst; withdrawing an output stream, at the output of the reactor; separating the output stream, making it possible to recover at least: on the one hand, the unsaturated product and, on the other hand, the first unsaturated compound and the second unsaturated compound; recycling the first unsaturated compound and the second unsaturated compound to the reactor; in which the first unsaturated compound is capable of producing an unsaturated coproduct, including at least 14 carbon atoms, by homometathesis; and in which the flow rates for feeding the reactor with first unsaturated compound and with second unsaturated compound are adjusted.

  一种通过交叉芳烃醚化反应合成不饱和产物的方法，其中包括：将至少含有8个碳原子的第一种不饱和化合物、含有少于8个碳原子的第二种不饱和化合物和芳烃醚化催化剂加入反应器；从反应器出口处取出输出流；分离输出流，使其至少可以回收：一方面是不饱和产物，另一方面是第一种不饱和化合物和第二种不饱和化合物；将第一种不饱和化合物和第二种不饱和化合物回收到反应器中；其中第一种不饱和化合物能够通过同源芳烃醚化反应产生至少含有14个碳原子的不饱和共产物；并且调整用于向反应器供给第一种不饱和化合物和第二种不饱和化合物的流量。
• Methyl Ricinoleate as Platform Chemical for Simultaneous Production of Fine Chemicals and Polymer Precursors
  作者：Antoine Dupé、Mathieu Achard、Cédric Fischmeister、Christian Bruneau

  DOI：10.1002/cssc.201200320

  日期：2012.11

  modification of methyl ricinoleate by etherification of the hydroxyl group was accomplished by using a nonclassical ruthenium‐catalyzed allylation reaction and also by esterification. Methyl ricinoleate derivatives were engaged in ring‐closing metathesis (RCM) reactions leading to biosourced 3,6‐dihydropyran and α,β‐unsaturated lactone derivatives with concomitant production of polymer precursors. Sequential

  通过使用非经典钌催化的烯丙基化反应以及酯化反应，可以通过羟基的醚化改性蓖麻油酸甲酯。蓖麻油酸甲酯衍生物参与闭环复分解（RCM）反应，从而导致生物来源的3,6-二氢吡喃和α，β-不饱和内酯衍生物，并同时产生聚合物前体。顺序RCM /加氢和RCM /交叉复分解也被用作合成四氢吡喃和内酯衍生物以及有价值的单体（即聚酰胺前体）的直接方法。