顺-10-十八碳烯酸 | 2442-70-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 顺-10-十八碳烯酸
• 中文别名: 顺式-10-十八碳烯酸
• 英文名称: cis-10-octadecenoic acid
• 英文别名: oleic acid；10-oleic acid；10c-Octadecensaeure；10-Oelsaeure；Δ¹⁰-cis-Octadecensaeure；cis-Δ¹⁰-Octadecensaeure；(Z)-octadec-10-enoic acid
• CAS: 2442-70-8
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: QXJSBBXBKPUZAA-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  顺-10-十八碳烯酸 在 indium(III) chloride 、 乙腈 作用下， 200.0 ℃ 、1.5 MPa 条件下， 反应 7.0h， 以97%的产率得到oleonitrile
  参考文献：
  名称：

  铟催化的硝化反应从羧酸直接合成腈：机理和动力学研究

  摘要：

  在催化剂存在下，使用乙腈作为溶剂和反应物，在200°C下，脂肪族和芳香族羧酸可定量转化为相应的腈。该转化基于酸-腈交换（即反硝化），并使用无毒且耐水的催化剂三氯化铟（InCl 3）。通过实验和计算研究了氮化的机理，并与先前提出的机理进行了比较。与通常认为的酰胺作为中间体形成相反，反硝化是一种平衡反应，并通过平衡的Mumm反应进行，并形成酰亚胺作为中间体。提出了用于该反应的简单且可逆的机理，该机理通过动力学测量以及反应中间体和反应机理的密度泛函理论计算得到验证。

  DOI：

  10.1021/acscatal.9b02779
• 作为产物：
  描述：

  ethyl 9-cyanononanoate 在 sodium phosphinate 、 水 、 sodium hexamethyldisilazane 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 顺-10-十八碳烯酸
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105

文献信息

• Synthesis of type I and IV cyanolipids
  作者：Mugio Nishizawa、Kenji Adachi、Yuji Hayashi

  DOI：10.1039/c39840001637

  日期：——

  Type I and IV cyanolipids, members of a unique class of plant lipid, have been synthesized efficiently by means of a novel cyanoesterification of aldehydes, and fully characterzed by spectral analysis; an artifical ‘type V’ cyanolipid has also been synthesized.

  I和IV型氰脂脂是植物脂质的一类成员，已通过醛的新型氰基酯化反应高效合成，并通过光谱分析充分表征。还合成了人造的“ V型”氰脂。
• Catalytic hydrogenation of linoleic acid on nickel, copper, and palladium
  作者：Yoshie Kitayama、Masahiro Muraoka、Megumi Takahashi、Tatsuya Kodama、Hirofumi Itoh、Eriko Takahashi、Mutsuo Okamura

  DOI：10.1007/bf02525461

  日期：1996.10

  The catalytic activity and selectivity for hydrogenation of linoleic acid were studied on Ni, Cu, and Pd catalysts. A detailed analysis of the reaction product was performed by a gas‐liquid chromatograph, equipped with a capillary column, and Fourier transform‐infrared spectroscopy. Geometrical and positional isomerization of linoleic acid occurred during hydrogenation, and many kinds of linoleic acid isomers (trans‐9,trans‐12; trans‐8,cis‐12 orcis‐9,trans‐13; cis‐9,trans‐12; trans‐9,cis‐12 andcis‐9,cis‐12 18∶2) were contained in the reaction products. The monoenoic acids in the partial hydrogenation products contained eight kinds of isomers and showed different isomer distributions on Ni, Cu, and Pd catalysts, respectively. The positional isomers of monoenoic acid were produced by double‐bond migration during hydrogenation. On Ni and Pd catalysts, the yield ofcis‐12 andtrans‐12 monoenoic acids was larger than that ofcis‐9 andtrans‐9 monoenoic acids. On the contrary, the yield ofcis‐9 andtrans‐9 monoenoic acids was larger than that ofcis‐12 andtrans‐12 monoenoic acids on Cu catalyst. From these results, it is concluded that the double bond closer to the methyl group (Δ12) and that to the carboxyl group (Δ9) show different reactivity for hydrogenation on Ni, Cu, and Pd catalysts. Monoenoic acid formation was more selective on Cu catalyst than on Ni and Pd catalysts.

  摘要 研究了 Ni、Cu 和 Pd 催化剂对亚油酸加氢反应的催化活性和选择性。利用配备毛细管色谱柱的气液相色谱仪和傅立叶变换红外光谱对反应产物进行了详细分析。氢化过程中亚油酸发生了几何和位置异构化，反应产物中含有多种亚油酸异构体（反式-9,反式-12；反式-8,顺式-12 或顺式-9,反式-13；顺式-9,反式-12；反式-9,顺式-12 和顺式-9,顺式-12 18∶2）。部分加氢产物中的单烯酸含有八种异构体，在镍、铜和钯催化剂上分别呈现出不同的异构体分布。单烯酸的位置异构体是在氢化过程中通过双键迁移产生的。在 Ni 和 Pd 催化剂上，顺式-12 和反式-12 单烯酸的产率大于顺式-9 和反式-9 单烯酸。相反，在铜催化剂上，顺-9 和反-9 单烯酸的产率大于顺-12 和反-12 单烯酸的产率。从这些结果可以得出结论，在镍、铜和钯催化剂上，与甲基（Δ12）较接近的双键和与羧基（Δ9）较接近的双键在氢化过程中表现出不同的反应活性。在铜催化剂上形成单烯酸比在镍和钯催化剂上更具选择性。
• Comprehensive gas chromatography-electron ionisation mass spectrometric analysis of fatty acids and sterols using sequential one-pot silylation: quantification and isotopologue analysis
  作者：Dick-Paul Kloos、Emmanuel Gay、Henk Lingeman、Franz Bracher、Christoph Müller、Oleg A Mayboroda、André M Deelder、Wilfried M A Niessen、Martin Giera

  DOI：10.1002/rcm.6923

  日期：2014.7.15

  Fatty acids and sterol lipids play crucial roles in several biological processes and several biological facts underline the interconnection between these lipid classes. Therefore, it is of interest to develop a comprehensive method analysing both classes in the form of their most favourable derivatives suitable for quantification and isotopologue analysis.

  脂肪酸和固醇脂在一些生物过程中起着至关重要的作用，并且一些生物学事实强调了这些脂类之间的相互联系。因此，有必要开发一种综合的方法，以最适合用于定量分析和同位素同位素分析的衍生物的形式分析这两种化合物。
• <scp>Visible‐Light Photoredox‐Catalyzed</scp> Hydrodecarboxylation and Deuterodecarboxylation of Fatty Acids
  作者：Yuan‐Li Sun、Fang‐Fang Tan、Rong‐Gui Hu、Chun‐Hong Hu、Yang Li

  DOI：10.1002/cjoc.202200143

  日期：2022.8.15

  We develop an efficient visible-light photoreodox-catalyzed hydrodecarboxylation and deuterodecarboxylation of fatty acids for alkanes and deuterium alkanes. The key to the efficient transformation should attribute to the co-catalysis of the suitable methoxy substituted acridine photocatalyst (Mes-1,3,6,8-tetramethoxy-Acr-3”,5”-dimethoxy-Ph) and the hydrogen atom transfer catalyst 4′,4′-dimethyl diphenyldisulfane

  我们为烷烃和氘烷烃开发了一种高效的可见光光氧化还原催化的脂肪酸加氢脱羧和氘脱羧。高效转化的关键在于合适的甲氧基取代吖啶光催化剂（Mes-1,3,6,8-tetramethoxy-Acr-3”,5”-dimethoxy-Ph）的共催化和氢原子转移催化剂 4',4'-二甲基二苯二硫烷，可能通过促进活性烷基自由基猝灭以克服竞争性均偶联产物，烯烃通过歧化反应，裂解产物通过 C-C 键 β-断裂。
• Enzymatic synthesis of amlodipine amides and evaluation of their anti-<i>Trypanosoma cruzi</i> activity
  作者：Orlando G. Elso、Augusto E. Bivona、Rocío Cenizo、Emilio L. Malchiodi、Guadalupe García Liñares

  DOI：10.1039/d2ob02271k

  日期：——

  new antiparasitic agents, we have enzymatically synthesized a series of amides derived from amlodipine, a calcium channel blocker used as an antihypertensive drug. Through lipase-catalyzed acylation with different carboxylic acids, nineteen amlodipine derivatives were obtained, eighteen of which were new compounds. To optimize the reaction conditions, the influence of several reaction parameters was

  随着我们关于开发新型抗寄生虫药的项目的推进，我们通过酶法合成了一系列源自氨氯地平的酰胺，氨氯地平是一种用作抗高血压药物的钙通道阻滞剂。通过脂肪酶催化与不同羧酸的酰化作用，得到了19个氨氯地平衍生物，其中18个为新化合物。为了优化反应条件，分析了几个反应参数的影响，发现了脂肪族羧酸和苯乙酸的不同要求。所有合成的化合物都被评估为抗克氏锥虫的抗增殖剂，克氏锥虫是美洲锥虫病（恰加斯病）的病原体。其中一些对T. cruzi的无鞭毛体形式表现出显着的活性，寄生虫的临床相关形式。在合成的化合物中，肉豆蔻酸和亚麻酸的衍生物显示出更高的功效和更低的细胞毒性。这些结果增加了酶促方法所显示的优势，例如温和的反应条件和低环境影响，使这种方法成为合成这些氨氯地平衍生物的有价值的方法，可用作有前途的抗寄生虫剂。