methyl 11-cyanoundec-10-enoate | 344611-29-6

• 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-10-enoate
• 英文别名: methyl (E)-11-cyanoundec-10-enoate
• CAS: 344611-29-6
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: RWSKIIGXUMTTSN-CSKARUKUSA-N

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

• 作为产物：
  描述：

  10-烯酸甲酯 在 ammonium hydroxide 、 2,2,6,6-四甲基哌啶氧化物 、 di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride 、 [Cu(MeCN)₄](OTf) 、 [1,3-bis(2,6-di-isopropylphenyl)-2-imidazolidinylidene]dichloro(o-isopropoxyphenylmethylene)ruthenium(II) 、 双氧水 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 21.0h， 生成 methyl 11-cyanoundec-10-enoate
  参考文献：
  名称：

  [EN] PREPARATION OF AMINO ACIDS AND AMINO ACID DERIVATIVES
  [FR] PRÉPARATION D'ACIDES AMINÉS ET DE DÉRIVÉS D'ACIDES AMINÉS

  摘要：

  这项发明涉及一种合成氨基酸或氨基酸衍生物的方法，包括功能化烯烃的交叉复分解以及串联氨基化-还原过程。氨基酸和氨基酸衍生物具有许多有趣的物理和化学性质，在汽车、燃料、电子和纺织工业中找到了许多用途。

  公开号：

  WO2018057290A1

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。
• Ruthenium–alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: a key step toward long-chain bifunctional and amino acid compounds
  作者：X. Miao、R. Malacea、C. Fischmeister、C. Bruneau、P. H. Dixneuf

  DOI：10.1039/c1gc15569e

  日期：——

  The ruthenium catalysed cross-metathesis of fatty-esters arising from plant oils with acrylonitrile is presented. The resulting linear nitrile ester products have potential as new intermediates for polyamides synthesis. A series of commercially available catalysts are able to promote the transformation of methyl 10-undecenoate 1, dimethyl octadec-9-en-1,18-dioate 5 and methyl ricinoleate 9 with acrylonitrile

  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。
• NYLON POLYMER AND PROCESS
  申请人：INVISTA North America S.a r.l.

  公开号：US20150011725A1

  公开（公告）日：2015-01-08

  Provided is a process for producing a nylon polymer comprising the steps of contacting an omega-terminal fatty acid or fatty acid ester with a pentenenitrile to produce a nitrile-functionalized unsaturated fatty acid or fatty acid ester, hydrogenating the nitrile-functionalized unsaturated fatty acid or fatty acid ester with hydrogen in the presence of a hydrogenation catalyst to produce a saturated amino acid and subjecting the saturated amino acid to polyamidation conditions to provide a nylon polymer.

  提供一种生产尼龙聚合物的方法，包括以下步骤：将ω-端脂肪酸或脂肪酸酯与戊二腈接触，以产生一种含有腈官能团的不饱和脂肪酸或脂肪酸酯，将这种腈官能团的不饱和脂肪酸或脂肪酸酯在氢化催化剂存在下与氢气加氢，以产生饱和氨基酸，并将饱和氨基酸在聚酰胺化条件下进行聚合，以提供尼龙聚合物。
• Preparation of amino acids and amino acid derivatives
  申请人：Umicore AG & Co. KG

  公开号：US10774035B2

  公开（公告）日：2020-09-15

  The invention relates to a method for synthesizing amino acids or amino acid derivatives involving cross metathesis of functionalized olefins and a tandem amination-reduction process. Amino acids and amino acid derivatives present many interesting physical and chemical properties finding many uses in the automotive, fuel, electronic, and textile industries.

  本发明涉及一种合成氨基酸或氨基酸衍生物的方法，包括官能化烯烃的交叉偏析和串联胺化还原过程。氨基酸和氨基酸衍生物具有许多有趣的物理和化学特性，在汽车、燃料、电子和纺织工业中用途广泛。
• Alkylidene-Ruthenium-Tin Catalysts for the Formation of Fatty Nitriles and Esters via Cross-Metathesis of Plant Oil Derivatives
  作者：Xiaowei Miao、Anton Blokhin、Alexandr Pasynskii、Sergey Nefedov、Sergey N. Osipov、Thierry Roisnel、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1021/om100372b

  日期：2010.11.8

  The reaction of SnCl2 with the Ru-Cl bond of the Grubbs I catalyst RuCl2(=CHPh)(PCy3)(2) (1) gives the complex [Ru(=CHPh)(SnCl3)(PCy3)](2)(mu-Cl)(3)}(-)[HPCy3](+) (2), but containing two diethyl ether solvate molecules. The formal insertion of SnCl2 into one Ru-Cl bond of the Hoveyda II catalyst RuCl2(=CH-C6H4OPri)H(2)IMes) (3) (H(2)IMes = N,N'-dimesityl-4,5-dihydroimidazol-2-ylidene) results in formation of the new complex RuCl(SnCl3)(=CH-C6H4OPri)(H(2)IMes) (4). The X-ray analyses of 2 and 4 show the presence of very short Ru-Sn bonds (2.5834(9) angstrom mean bond for 2 and 2.5925(12) angstrom for 4) and the retention of short Ru=C bonds (1.895(10) and 1.825(8) angstrom, respectively). Complex 4 shows an excellent catalytic activity for the cross-metathesis of plant oil derivatives, the C11 omega-unsaturated ester and aldehyde and the unsaturated C18 diester with acrylonitrile, and a good activity for their cross-metathesis with methyl acrylate. Good to excellent yield of alpha,omega-bifunctional compounds, precursors of polyesters and polyamides, were obtained. Complex 2 shows catalytic activity for the self-metathesis of C11 omega-unsaturated aldehyde at low concentration to produce C20 alpha,omega-dialdehyde.