1-甲基十一碳-2-烯酸酯 | 22104-71-8

• 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: 1-甲基十一碳-2-烯酸酯
• 英文名称: methyl undec-2-enoate
• 英文别名: 1-methylundec-2-enoate；undec-2-enoic acid methyl ester；methyl undecylenate；methyl 2-undecenoate；Methyl-undecenoate
• CAS: 22104-71-8
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: FDNCPIRKQFHDBX-UHFFFAOYSA-N

物化性质

• 沸点：
  254.9±9.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基十一碳-2-烯酸酯 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~20.0 ℃ 、413.7 kPa 条件下， 反应 101.0h， 生成 (R)-methyl 3-(ethoxycarbonylamino)undecanoate
  参考文献：
  名称：

  Efficient synthesis of β’-amino-α,β-unsaturated ketones

  摘要：

  一种通用且简单的程序，通过七个步骤，从α，β不饱和酯中制备手性β'-氨基-α，β-烯酮已经被描述。使用Horner–Wadsworth–Emmons反应作为生成β'-氨基-α，β-烯酮的关键步骤，可以在温和条件下以中等至高收率获得一系列底物。

  DOI：

  10.3762/bjoc.9.52
• 作为产物：
  描述：

  1-Chloroundec-2-ynylsulfanylbenzene 在 盐酸 、 碘 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 11.0h， 生成 1-甲基十一碳-2-烯酸酯
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Aldehydes and Methyl Carboxylic Esters from 2-Acetylenic Phenyl Sulfides.

  摘要：

  2-Alkynylthio benzenes were reduced to 2-Alkenylthio benzenes with diisobutyl aluminum hydride. Mono chlorination of these compounds with sulfuryl chloride and pyridine followed by hydrolysis, in the presence of Cu-II salts, gave alpha,beta-unsaturated aldehydes.2-Alkynylthio benzenes were converted into 2-Alkynyl 1,1-bis thiobenzenes by monochlorination with sulfuryl chloride and pyridine followed by treatment with thiophenol and triethylamine. These substances were then converted to alpha,beta-unsaturated methyl carboxylic esters by way of isomerization with sodium methoxide to the corresponding allene and treatment with hydrochloric acid and methanolysis in the presence of iodine.

  DOI：

  10.1080/00397919708005915

文献信息

• Olefin cross-metathesis as a valuable tool for the preparation of renewable polyesters and polyamides from unsaturated fatty acid esters and carbamates
  作者：Matthias Winkler、Michael A. R. Meier

  DOI：10.1039/c4gc00273c

  日期：——

  Olefin cross-metathesis of unsaturated fatty acid methyl ester (FAME) derived benzyl carbamates with methyl acrylate is described. The obtained by-product, an α,β-unsaturated ester, was further modified via thia-Michael addition reactions in order to synthesize branched AA-type or AB-type monomers for the preparation of polyesters, which are tuneable by oxidation. Cross-metathesis of fatty acid derived

  描述了不饱和脂肪酸甲酯（FAME）衍生的苄基氨基甲酸酯与丙烯酸甲酯的烯烃交叉复分解。将获得的副产物α，β-不饱和酯通过以下方法进一步改性为了合成支链的AA型或AB型单体以制备聚酯，可通过氧化调节Thia-Michael加成反应。脂肪酸衍生的氨基甲酸酯的交叉复分解用作制备线性AB型单体的新方法，可用于制备可再生聚酰胺PA11，PA12和PA15。必要的脂肪酸氨基甲酸酯是通过应用催化的Lossen重排程序制备的。提出的合成策略具有生物来源的单体制备聚酰胺的生产潜力。所有制备的聚合物均通过NMR，SEC和DSC分析进行了全面表征。另外，测定了所制备的长链聚酰胺PA15的杨氏模量。
• An Efficient Method for the Direct Peroxygenation of Various Olefinic Compounds with Molecular Oxygen and Triethylsilane Catalyzed by a Cobalt(II) Complex
  作者：Shigeru Isayama

  DOI：10.1246/bcsj.63.1305

  日期：1990.5

  An efficient method for the direct peroxygenation of various olefinic compounds with molecular oxygen and triethylsilane (Et3SiH) was developed by the use of a catalytic amount of a bis(1,3-diketonato)cobalt(II) complex. According to the above method, 1-phenyl-3-triethylsilydioxybutane (2) was directly produced from 4-phenyl-1-butene (1) by means of a reaction with O2 and Et3SiH at room temperature. Styrene (3) and ethyl acrylate (5a) were also smoothly peroxygenated to give 1-phenyl-1-triethylsilyldioxyethane (4) and ethyl 2-triethylsilyldioxypropionate (6a) by using a small amount of t-BuOOH as an initiator. The successive desilylation of 6a and reduction of the resulting ethyl 2-hydroperoxypropionate (8a) afforded the corresponding alcohol, ethyl lactate (10a), in a high yield. The synthetic utility of the present peroxygenation reaction was demonstrated in the preparation of α-hydroxy esters 10a–e from several α,β-unsaturated esters 5a–e via the corresponding triethylsilyldioxy derivatives.

  一种使用双(1,3-二酮基)钴(II)配合物催化剂对各种烯烃化合物进行分子氧和三乙基硅烷(Et3SiH)直接过氧化的高效方法已被开发。根据上述方法，通过在室温下使用O2和Et3SiH与4-苯基-1-丁烯(1)反应，直接生成了1-苯基-3-三乙基硅氧基丁烷(2)。此外，苯乙烯(3)和丙烯酸乙酯(5a)也能顺利地进行过氧化反应，使用少量t-BuOOH作为引发剂，分别得到1-苯基-1-三乙基硅氧基乙烷(4)和乙基2-三乙基硅氧基丙酸酯(6a)。接着对6a进行脱硅基化反应，并将其产物乙基2-氢过氧化丙酸酯(8a)还原，以高产率获得了相应的醇，即乙醇酸乙酯(10a)。本过氧化反应的合成实用性通过从几种α,β-不饱和酯5a–e制备相应的三乙基硅氧基衍生物，进而合成α-羟基酯10a–e得到了展现。
• Effects of acidity and immiscibility of lactam-based Brønsted-acidic ionic liquids on their catalytic performance for esterification
  作者：Hancheng Zhou、Jing Yang、Linmin Ye、Haiqiang Lin、Youzhu Yuan

  DOI：10.1039/b921081d

  日期：——

  Several lactam-based Brønsted-acidic ionic liquids with different acidities were synthesized and applied to the esterification of carboxylic acids with alcohols. High conversion and perfect selectivity were obtained under mild conditions. Among the ionic liquids investigated, those having a methyl sulfonate anion (which has weaker acidity than those with a tetrafluoroborate anion) afforded the highest activity for esterification. The results indicated that the acidity and immiscibility of Brønsted-acidic ionic liquids has a synergistic effect on their esterification performance. Furthermore, after removal of water under vacuum, such ionic liquids could be reused several times without substantial loss of activity.

  合成了几种不同酸性的基于内酰胺的布朗斯台德酸性离子液体并将其应用于羧酸与醇的酯化反应。在温和条件下获得了高转化率和良好的选择性。在研究的离子液体中，那些具有甲磺酸根阴离子（其酸性比具有四氟硼酸根阴离子的酸性更弱）的离子液体在酯化反应中表现出最高的活性。结果表明，布朗斯台德酸性离子液体的酸性和不相容性对其酯化性能具有协同作用。此外，在真空下去除水分后，这些离子液体可以重复使用多次，活性几乎没有实质性损失。
• Access to 2,6-Disubstituted Piperidines: Control of the Diastereoselectivity, Scope, and Limitations. Applications to the Stereoselective Synthesis of (−)-Solenopsine A and Alkaloid (+)-241D
  作者：Isabelle Abrunhosa-Thomas、Aurélie Plas、Alexandre Vogrig、Nishanth Kandepedu、Pierre Chalard、Yves Troin

  DOI：10.1021/jo302712f

  日期：2013.3.15

  Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (−)-solenopsine A and alkaloid (+)-241D.

  通过手性β'-氨基甲酸酯-α，β-不饱和酮的分子内反应，描述了2,6-顺式或2,6-反式二取代的哌啶的非对映选择性制备的范围和局限性。该方法已应用于一些很好选择的例子的全合成，例如（-）-比尔诺西汀A和生物碱（+）-241D。
• Room-temperature Pd-catalyzed methoxycarbonylation of terminal alkynes with high branched selectivity enabled by bisphosphine-picolinamide ligand
  作者：Ding Liu、Miaolin Ke、Tong Ru、Yingtang Ning、Fen-Er Chen

  DOI：10.1039/d1cc06098h

  日期：——

  The challenging room temperature Pd-catalyzed methoxycarbonylation for a wide array of alkynes with excellent branched selectivity has been developed.

  已开发出具有出色支链选择性的广泛烯烃室温Pd催化的甲氧羰基化反应。