Methyl 11-cyanoundec-2-enoate | 1346519-50-3

• 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 11-cyanoundec-2-enoate
• CAS: 1346519-50-3
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: JCFGOQKQHKCNFK-UHFFFAOYSA-N

物化性质

• 沸点：
  352.5±25.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 11-cyanoundec-2-enoate 在 Hoveyda-Grubbs catalyst second generation 、 potassium tert-butylate 、 氢气 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、2.0 MPa 条件下， 反应 40.0h， 以102 mg的产率得到methyl 12-aminododecanoate
  参考文献：
  名称：

  聚酰胺纤维 可再生的10-十一碳烯腈的前体和 丙烯酸甲酯 通过 烯烃 交叉复分解

  摘要：

  钌催化 交叉复分解 的 不饱和脂肪酸蓖麻油衍生的衍生物10-十一碳烯腈1丙烯酸甲酯生产高周转数的C12腈酸酯。该产品有潜力作为一种新的生物来源的中间体，用于生产聚酰胺纤维。这条路线与10-十一碳烯酸甲酯 和 丙烯腈导致相同的C12α，ω-氨基酯7之后氢化 碳-碳双键和腈官能度的关系。

  DOI：

  10.1039/c2gc35648a
• 作为产物：
  描述：

  2-十一烯酸 在 Hoveyda-Grubbs catalyst second generation 、 氨 、 zinc(II) oxide 作用下， 以 甲苯 为溶剂， 100.0~265.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 Methyl 11-cyanoundec-2-enoate
  参考文献：
  名称：

  PROCESS FOR THE SYNTHESIS OF C11 AND C12 OMEGA-AMINOALKANOIC ACID ESTERS COMPRISING A NITRILATON STEP

  摘要：

  一种合成C11和C12 ω-氨基酸酯的方法，包括在气相或混合气液相中进行连续硝化反应的步骤，以及使用C10和C11 ω-烯酸酯作为原料的歧化和还原步骤。

  公开号：

  US20140200358A1

文献信息

• PROCESS FOR PREPARING SATURATED AMINO ACIDS OR SATURATED AMINO ESTERS COMPRISING A METATHESIS STEP
  申请人：Couturier Jean Luc

  公开号：US20130116458A1

  公开（公告）日：2013-05-09

  The subject matter of the invention is a process for synthesizing a saturated long-chain o.,0)-amino ester (acid) obtained in a first step by cross-metathesis between an acrylic first compound and a monounsaturated second compound comprising at least one nitrile, acid or ester trivalent function, one of these compounds comprising a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and in a second step by hydrogenation of the monounsaturated nitrile ester (acid) obtained in the presence of the metathesis catalyst of the preceding stop, acting as a hydrogenation catalyst.

  发明的主题是一种合成饱和长链O.,0）-氨基酯（酸）的过程，该过程首先通过交叉复分解在丙烯酸第一种化合物和至少含有一种腈、酸或酯三价功能的单不饱和第二种化合物之间进行，其中一种化合物含有腈功能，另一种化合物含有酸或酯功能，在钌卡宾复分解催化剂的存在下，然后在第二步中，通过氢化在前一步中获得的单不饱和腈酯（酸），在前一步中的复分解催化剂作为氢化催化剂的作用下。
• METHOD FOR SYNTHESIZING AN OMEGA-AMINO ACID OR ESTER FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Couturier Jean-Luc

  公开号：US20140187808A1

  公开（公告）日：2014-07-03

  A method for synthesizing ω-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ω-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ω-amino acid (ester) of formula R3OOC—(CH2) q —CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH═CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.

  一种从天然不饱和脂肪酸通过中间体ω-不饱和腈化合物合成ω-氨基-烷酸或其酯的方法。该方法实施简单，与已知方法相比，避免了由反应副产物导致的环境限制和经济劣势。该方法包括从公式为(R1-CH═CH—(CH2)p-COO)xR2的单不饱和脂肪酸(酯)合成公式为R3OOC—( )q— NH2的ω-氨基酸(酯)，其中R3是H或n-丁基基团，q是2到13之间的整数指数，x代表1、2或3，R1是H或含4到11个碳原子的烃基团，适当情况下还含有羟基，R2是H或含2到4个碳原子的烷基基团，可包含一个或多个杂原子，p是2到11之间的整数指数，包括氨化反应步骤。
• Tandem Catalytic Acrylonitrile Cross-Metathesis and Hydrogenation of Nitriles with Ruthenium Catalysts: Direct Access to Linear α,ω-Aminoesters from Renewables
  作者：Xiaowei Miao、Cédric Fischmeister、Christian Bruneau、Pierre H. Dixneuf、Jean-Luc Dubois、Jean-Luc Couturier

  DOI：10.1002/cssc.201200086

  日期：2012.8

  Fraternité, Solidarité & complémentarité en Catalyse: Tandem alkene cross‐metathesis of acrylonitrile with long‐chain alkene and hydrogenation catalysis is performed by using a single ruthenium‐alkylidene catalyst precursor. The protocol allows the catalytic transformation of unsaturated fatty acids, derivatives of plant oils, into α,ω‐aminoesters. A key step involves the reduction of nitrile‐ester

  催化，立体和催化：丙烯腈与长链烯烃的双烯烃交叉复分解和加氢催化反应是通过使用单一的钌-亚烷基催化剂前体进行的。该协议允许将植物油的衍生物不饱和脂肪酸催化转化为α，ω-氨基酯。关键步骤包括在温和条件下，将烯烃复分解催化剂残留物还原为腈的中间体，将其转变为氨基酯（聚酰胺的前体）。
• PROCESS FOR THE SYNTHESIS OF OMEGA-UNSATURATED NITRILE-ACID/ESTER IN WHICH TWO TYPES OF CROSS METATHESIS ARE ALTERNATED CONSECUTIVELY, SWING PROCESS
  申请人：ARKEMA FRANCE

  公开号：US20150336879A1

  公开（公告）日：2015-11-26

  A process for the synthesis of a monounsaturated nitrile-ester (acid) by cross metathesis starting from an unsaturated compound I including at least one trivalent nitrile, acid or ester functional group, wherein the process includes a stage in which two types of cross metathesis are alternated consecutively: — a first type of cross metathesis cm1 with an acrylic compound II chosen from acrylonitrile, acrylic acid or an acrylic ester, one of the compounds I or II including a nitrile functional group and the other of these compounds II or I including an acid or ester functional group, and—a second type of cross metathesis cm2 with a light C 2 to C 4 alkene compound III. Also, a process for the synthesis of an α,ω-amino ester (acid) obtained by a process including a stage in which the two types of cross metathesis defined above are alternated consecutively, followed by a hydrogenation stage.

  一种通过交叉烯烃反应从不饱和化合物I开始合成单不饱和腈酯（酸）的方法，其中不饱和化合物I包括至少一个三价腈酸，酸或酯官能团，在该过程中包括一个阶段，其中连续交替两种交叉烯烃反应类型：-第一种交叉烯烃反应cm1与丙烯腈，丙烯酸或丙烯酯中选择的一种丙烯化合物II进行反应，其中化合物I或II包括腈官能团，而这两种化合物II或I中的另一种包括酸或酯官能团，-第二种交叉烯烃反应cm2与轻质C2到C4烯烃化合物III进行反应。此外，还提供了一种通过交替进行上述两种交叉烯烃反应的阶段，然后进行氢化阶段而获得的α，ω-氨基酯（酸）的合成方法。
• PROCESS FOR PREPARING AMINO ACIDS OR ESTERS COMPRISING A METATHESIS STEP
  申请人：Couturier Jean-Luc

  公开号：US20140163196A1

  公开（公告）日：2014-06-12

  A process for synthesizing a long-chain saturated α,ω-amino ester (acid) including from 6 to 17 carbon atoms, said process including a first step of cross metathesis between a first acrylic compound chosen from acrylonitrile, acrylic acid or an acrylic ester and a second monounsaturated compound including at least one nitrile, acid or ester trivalent function, one of these compounds including a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and a second step of hydrogenation of the monounsaturated nitrile-ester (acid) obtained, wherein said monounsaturated compound including at least one nitrile, acid or ester trivalent function has previously been subjected to a purification by thermal and/or chemical treatment.

  一种合成长链饱和α,ω-氨基酯（酸）的方法，包括6至17个碳原子，该方法包括第一步交叉烯烃基化反应，反应物为从丙烯腈、丙烯酸或丙烯酯中选择的第一丙烯酸化合物和含有至少一个腈、酸或酯三价功能的第二单不饱和化合物，其中这些化合物中一个包括腈功能，另一个包括酸或酯功能，在钌卡宾烯烃交联催化剂的存在下进行，并且第二步对所得的单不饱和腈酯（酸）进行氢化，其中所述含有至少一个腈、酸或酯三价功能的单不饱和化合物已经经过热和/或化学处理的纯化。