十三碳二酸二甲酯 | 1472-87-3

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: 十三碳二酸二甲酯
• 中文别名: 巴西酸二甲酯；巴西二烯酸二甲酯
• 英文名称: dimethyl 1,11-undecanedicarboxylate
• 英文别名: tridecanedioic acid dimethyl ester；1,13-tridecanedioic acid dimethyl ester；Dimethyl tridecanedioate
• CAS: 1472-87-3
• 化学式: C₁₅H₂₈O₄
• mdl: MFCD00008464
• 分子量: 272.385
• InChiKey: WWSBQOYADFGDQE-UHFFFAOYSA-N

物化性质

• 熔点：
  35-37 °C(lit.)
• 沸点：
  326-328 °C(lit.)
• 密度：
  0.9913 (rough estimate)
• 闪点：
  >230 °F
• LogP：
  4.430 (est)
• 保留指数：
  1976.8
• 稳定性/保质期：

  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.866
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2917190090
• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340
• 危险性描述：
  H302
• 储存条件：
  常温、避光、存放在通风干燥处。

反应信息

• 作为反应物：
  描述：

  十三碳二酸二甲酯 在 氯化亚砜 、 barium hydroxide octahydrate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 癸烷
  参考文献：
  名称：

  NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer

  摘要：

  The development of "molecular rulers" would allow one to quantitatively locate the penetration depth of intercalants within lipid bilayers. To this end, an attempt was made to correlate the C-13 NMR chemical shift of polarizable "reporter" carbons (e.g., carbonyls) of intercalants within DMPC liposomal bilayers - with the polarity it experiences, and with its Angstrom distance from the interface.This requires families of molecules with two "reporter carbons" separated by a known distance, residing at various depths/polarities within the bilayer. For this purpose, two homologous series of dicarbonyl compounds, methyl n-oxooctadecanoates and the corresponding n-oxooctadecanoic acids (n = 4-16), were synthesized. To assist in assignment and detection several homologs in each system were prepared (13)C(-)enriched in both carbonyls. Within each family, the number of carbons and functional groups remains the same, with the only difference being the location of the second ketone carbonyl along the fatty acid chain. Surprisingly, the head groups within each family are not anchored near the lipid-water interface, nor are they even all located at the same depth. Nevertheless, using an iterative best fit analysis of the data points enables one to obtain an exponential curve. The latter gives substantial insight into the correlation between polarity (measured in terms of the Reichardt polarity parameter, E-T(30)) and penetration depth into the liposomal bilayer. Still missing from this curve are data points in the moderate polarity range. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.07.007
• 作为产物：
  描述：

  10-烯酸甲酯 、 甲烷三甲酸三甲酯 在 二叔丁基过氧化物 作用下， 生成 十三碳二酸二甲酯
  参考文献：
  名称：

  Radical Addition of Carboxylic Acids and Carboxylic Acid Derivatives to Unsaturated Compounds as a Synthetic Method

  摘要：

  在简要讨论了自由基加成到烯烃的机制以及引发自由基链的可能途径之后，该反应被描述为一种制备羧酸衍生物的合成方法。选取的制备程序和包含制备数据的表格显示了该方法广泛的适用性。不饱和化合物——开链、环状或双环的未取代和取代的烯烃，以及二烯烃和炔烃，可以在各种条件下与简单和取代的单羧酸和二羧酸衍生物以及三羧酸酯进行自由基反应。自由酸、酯、内酯、酰胺、内酰胺、酐、腈和酰氯，以及α-氨基酸衍生物和α-卤代酸，在与烯烃发生加成反应时，如果至少有一个氢或卤素原子位于酸或酸衍生物的α原子上。注意到1:1加合物的产率对反应参数的依赖性，并描述了对α-烯烃具有选择性的加成反应的可能性。

  DOI：

  10.1055/s-1970-21583

文献信息

• Synthesis and Biological Activities of Acetylenic Fatty Acids and Their Esters
  作者：Munehiro Nakatani、Yuji Fukunaga、Hiroyuki Haraguchi、Makoto Taniguchi、Tsunao Hase

  DOI：10.1246/bcsj.59.3535

  日期：1986.11

  Eight terminal acetylenic fatty acids from 5-hexynoic to 12-tridecynoic acids and their methyl, ethyl, and isopropyl esters were synthesized via o-nitrophenyl selenides. These acids and esters all showed inhibitory effect on lettuce seed germination and seedling growth. The effect was dependent on the number of carbon atoms in acetylenic chain. 8-Nonynoic acid showed potent activity, and its methyl ester was the most effective among the test compounds. In addition, the acids showed antifungal activity which increased as the number of carbon atoms increased.

  通过邻硝基苯硒醚合成了 8 种末端炔脂肪酸:从 5-己炔酸到 12-十三炔酸及其甲基、乙基和异丙基酯。这些酸和酯对莴苣种子萌发和幼苗生长均有抑制作用。其作用效果依赖于炔链碳原子数。8-壬炔酸具有强烈的活性,其甲酯在所测试样品中活性最强。此外,这些酸具有抗菌活性,且随碳原子数的增加而增强。
• Ruthenium catalysed oxidation without CCl4 of oleic acid, other monoenic fatty acids and alkenes
  作者：François Zimmermann、Eric Meux、Jean-Luc Mieloszynski、Jean-Marie Lecuire、Nicolas Oget

  DOI：10.1016/j.tetlet.2005.03.052

  日期：2005.5

  Ruthenium catalysed oxidation of alkenes and monoenic fatty acids is reported. The study of the influence of cosolvents (H2O/MeCN/X) shows that toxic CCl4 initially used in the Sharpless system (H2O/MeCN/CCl4) can be avoided and demonstrates that the oxidative cleavage of CC bond could be accomplished in good yields with H2O/MeCN/AcOEt solvent system in a ratio 3/2/2, respectively.

  据报道，钌催化烯烃和单烯脂肪酸的氧化。对助溶剂（H 2 O / MeCN / X）影响的研究表明，可以避免最初在Sharpless系统中使用的有毒CCl 4（H 2 O / MeCN / CCl 4），并且证明了CC键的氧化裂解可以用比例为3/2/2的H 2 O / MeCN / AcOEt溶剂体系可实现高收率。
• Manganese and rhenium-catalyzed selective reduction of esters to aldehydes with hydrosilanes
  作者：Duo Wei、Ruqaya Buhaibeh、Yves Canac、Jean-Baptiste Sortais

  DOI：10.1039/d0cc03580g

  日期：——

  The selective reduction of esters to aldehydes, via the formation of stable alkyl silyl acetals, was, for the first time, achieved with both manganese, –Mn2(CO)10– and rhenium –Re2(CO)10– catalysts in the presence of triethylsilane as reductant. These two methods provide a direct access to a large variety of aliphatic and aromatic alkyl silyl acetals (30 examples) and to the corresponding aldehydes

  通过锰，-Mn 2（CO）10-和rh-Re 2（CO）10-锰催化剂的首次实现，通过形成稳定的烷基甲硅烷基缩醛将酯选择性还原为醛。存在三乙基硅烷作为还原剂。通过这两种方法，水解后可以直接进入大量的脂族和芳族烷基甲硅烷基缩醛（30个实例）和相应的醛（13个实例）。在室温下，在光照射条件下（LED，365 nm，40 W，9 h），反应以优异的收率和高选择性进行。
• Zirconium Borohydride - a Versatile Reducing Agent for the Reduction of Electrophilic and Nucleophilic Substrates
  作者：S. Narasimhan、R. Balakumar

  DOI：10.1080/00397910008087061

  日期：2000.12

  Abstract Zirconium borohydride, a potential reducing agent, reduces acids, esters, imines to the corresponding alcohols and secondary amines in good yield at room temperature within two hours. This facile reducing property was taken advantage off in the synthesis of pheromones and some novel chiral precursors for asymmetric synthesis.

  摘要 硼氢化锆是一种潜在的还原剂，可在室温下两小时内以良好的收率将酸、酯、亚胺还原为相应的醇和仲胺。在信息素和一些用于不对称合成的新型手性前体的合成中利用了这种简便的还原特性。
• A Simple Alkene -Catalyzed Reduction of Aromatic Esters to Alcohols by Zinc Borohydride
  作者：S. Narasimhan、S. Madhavan、K. Ganeshwar Prasad

  DOI：10.1080/00397919708006037

  日期：1997.2

  Abstract Reactivity of Zn(BH4)2 was modified by adding cyclohexene to achieve the reduction of aromatic esters to alcohols which reaction was not possible previously because of the mild nature of the reagent. Functional groups like Cl and nitro were tolerated.

  摘要 Zn(BH4)2 的反应性通过加入环己烯来实现将芳香酯还原为醇，由于该试剂性质温和，以前不可能发生这种反应。可以容忍像 Cl 和硝基这样的官能团。

表征谱图