Dimethyl (E)-octadec-9-enedioate | 24753-49-9

• 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: Dimethyl (E)-octadec-9-enedioate
• 英文别名: (E)-dimethyl octadec-9-enedioate；trans-dimethyl 9-octadecene-1,18-dioate；dimethyl 9-octadecenedioate
• CAS: 24753-49-9
• 化学式: C₂₀H₃₆O₄
• 分子量: 340.503
• InChiKey: HGGLIXDRUINGBB-ONEGZZNKSA-N

物化性质

• 沸点：
  417.8±38.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl (E)-octadec-9-enedioate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以67%的产率得到(9Z)-9-十八碳烯二酸
  参考文献：
  名称：

  A Synthesis of (Z)-Octadec-9-enedioic Acid

  摘要：

  壬二酸单甲酯被转化成两个片段，即[8-（甲氧基-羰基）辛基]三苯基溴化膦和 9-氧代壬酸甲酯。这两个片段之间的维蒂希反应生成了 (Z)-9- 十八碳二烯酸二甲酯，随后水解得到了标题中的二元酸。有趣的是，在已发表的利用热带念珠菌突变菌株的程序中，可以直接从油酸中获得相同的二元酸。

  DOI：

  10.1071/ch9951893
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 、 锌 作用下， 生成 Dimethyl (E)-octadec-9-enedioate
  参考文献：
  名称：

  Dupont et al., Bulletin de la Societe Chimique de France, 1956, p. 819,823

  摘要：

  DOI：

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。
• [EN] METHOD FOR PRODUCING OMEGA-HYDROXY FATTY ACID ESTER AND PRECURSOR COMPOUND THEREOF<br/>[FR] PROCÉDÉ DE PRODUCTION D'ESTER D'ACIDE OMÉGA-HYDROXY GRAS ET SON COMPOSÉ PRÉCURSEUR
  申请人：KAO CORP

  公开号：WO2016103677A1

  公开（公告）日：2016-06-30

  Provided is a method for producing a compound represented by Formula (III) while the production of by-products due to, for example, dimerization of a raw material or isomerization of a double bond position is suppressed. The method is a method for producing omega-hydroxy fatty acid ester and a precursor compound thereof of Formula (III), in which an alcohol derivative and a carboxylic acid derivative are subjected to a metathesis reaction in the presence of a catalyst to obtain a compound of Formula (III), wherein the alcohol derivative is at least one selected from the group consisting of a compound of Formula (VI) and a compound of Formula (I), and the carboxylic acid derivative is at least one selected from the group consisting of a compound of Formula (VII) and a compound of Formula (II), wherein the case where the alcohol derivative is formed of a compound of Formula (I) and the carboxylic acid derivative is formed of a compound of Formula (II) is excluded,

  提供了一种生产由公式（III）表示的化合物的方法，同时抑制了例如由于原料的聚合或双键位置的异构化而产生的副产品。该方法是一种生产omega-羟基脂肪酸酯及其公式（III）的前体化合物的方法，其中醇衍生物和羧酸衍生物在催化剂的存在下进行烯烃复分解反应以获得公式（III）的化合物，其中醇衍生物至少是公式（VI）的化合物和公式（I）的化合物中的一种，羧酸衍生物至少是公式（VII）的化合物和公式（II）的化合物中的一种，其中醇衍生物由公式（I）的化合物构成且羧酸衍生物由公式（II）的化合物构成的情况被排除。
• [EN] ACID CATALYZED OLIGOMERIZATION OF ALKYL ESTERS AND CARBOXYLIC ACIDS<br/>[FR] OLIGOMÉRISATION À CATALYSE ACIDE D'ESTERS D'ALKYLE ET D'ACIDES CARBOXYLIQUES
  申请人：ELEVANCE RENEWABLE SCIENCES

  公开号：WO2014153406A1

  公开（公告）日：2014-09-25

  The oligomerization of certain carboxylic acids and alkyl esters derived from natural oils is disclosed. This includes the oligomerization of C10-17 unsaturated carboxylic acids such as 9-decenoic acid, where the oligomerization yields a mixture of mono-, di- and tri-carboxylic acids. This also includes the oligomerization of certain alkyl esters, including the oligomerization of C10-17 unsaturated alkyl esters such as methyl 9-decenoate (9-DAME), where the oligomerization yields a mixture of mono-, di- and tri-carboxylic acid esters. Various end use applications for the oligomerized carboxylic acids and oligomerized alkyl esters are also disclosed.

  披露了某些从天然油脂衍生而来的羧酸和烷基酯的寡聚。这包括C10-17不饱和羧酸如9-癸烯酸的寡聚，其中寡聚产生了单羧酸、二羧酸和三羧酸的混合物。这也包括某些烷基酯的寡聚，包括C10-17不饱和烷基酯如甲基9-癸烯酸酯（9-DAME）的寡聚，其中寡聚产生了单羧酸酯、二羧酸酯和三羧酸酯的混合物。还披露了寡聚羧酸和寡聚烷基酯的各种最终用途应用。
• 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—(CH2)m—CH═CH—(CH2)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CH2NH2，如果R2为CN，则R3只能为CN；最后，将得到的通式为R3—CH═CH—(CH2)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。
• Metathesis reactions of unsaturated esters catalyzed by homogenous tungsten complexes. Syntheses of civetone and macrolides
  作者：Jiro Tsuji、Shohei Hashiguchi

  DOI：10.1016/s0022-328x(00)80988-2

  日期：1981.9

  obtained by the metathesis of ethyl oleate, was subjected to the Dieckmann cyclization. The cyclized product was decarboxylated to give civetone as a mixture of the cis and trans isomers. Preliminary studies of macrolide synthesis by the intramolecular metathesis of oleyl oleate and 10-undecenyl 10-undecenoate to afford 9-octadecen-18-olide and 10-eicosen-20-olide, respectively, have been carried out.

  甲基10-十一烯酸的复分解反应，油酸甲酯和油乙酸在使用WCL进行了6和WOCL 4作为primarycatalysts和SnMe 4，PbMe 4中，Cp 2时间2，1和Cp 2 ZrMe 2作为助催化剂。发现催化剂体系WOCl 4 / Cp 2 TiMe 2对于不饱和酯的复分解非常活跃，并且比体系WCl 6 / SnMe 4更好。。将通过油酸乙酯复分解获得的9-十八碳烯-1,18-二酸二乙酯进行狄克曼环化。使环化产物脱羧，得到西维酮，为顺式和反式异构体的混合物。通过油酸油酯和10-十一碳烯基10-十一碳烯酸酯的分子内复分解合成大环内酯的初步研究已经分别得到9-十八碳烯-18-内酰胺和10-二十碳烯-20-内酰胺。