ethyl 2-methyldeca-2,3-dienoate | 316372-83-5

• 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: ethyl 2-methyldeca-2,3-dienoate
• CAS: 316372-83-5
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: WTHTUPNXGABCEW-UHFFFAOYSA-N

物化性质

• 沸点：
  75-80 °C(Press: 1 Torr)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  ethyl 2-methyldeca-2,3-dienoate 在 lithium diisopropyl amide 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以80%的产率得到ethyl 2-fluoro-2-methyldec-3-ynoate
  参考文献：
  名称：

  Highly Regioselective Fluorination and Iodination of Alkynyl Enolates

  摘要：

  A simple yet efficient approach to various functionalized quaternary alpha-alkynyl alpha-fluoro esters and gamma-iodoallenoates from readily available allenoates through an alkynyl enolate intermediate generated by LDA is presented. Reaction of this alkynyl enolate with NFSI gives the alpha-product (alpha-alkynyl-alpha-fluoro ester), whereas the reaction of the silyl ether of alkynyl enolate with I-2 gives solely the gamma-product (iodoallenoate).

  DOI：

  10.1021/ol802451e
• 作为产物：
  描述：

  庚酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl 2-methyldeca-2,3-dienoate
  参考文献：
  名称：

  季碳中心对映选择性构建中烯醇锂与锂-炔相互作用：(+)-Goniomitine 的简明合成

  摘要：

  我们报道了一种直接对映选择性烷基化形成四级立体中心的 3-炔酸和 2,3-链烯二酸的方法，并将该方法应用于复杂生物碱 (+)-goniomitine 的全对映选择性合成。晶体学研究强调了手性锂聚集中间体中锂和炔基之间的阳离子-π相互作用。

  DOI：

  10.1002/anie.202209987

文献信息

• Synthesis of Functionalized α,α-Disubstituted β-Alkynyl Esters from Allenoates through an Alkynylenolate Intermediate
  作者：Weibo Wang、Bo Xu、Gerald B. Hammond

  DOI：10.1021/ol801287t

  日期：2008.9.1

  Highly substituted alpha,alpha-disubstituted beta-alkynyl esters are readily prepared from allenyl esters and either alkyl halide, acid chloride, or alkyl chloroformate, mediated by an amide base. This highly efficient and mild process tolerates various functional groups and provides alpha,alpha-disubstituted beta-alkynyl esters in good to excellent yields. This method is especially suitable for the

  高取代度的α，α-二取代的β-炔基酯很容易由烯丙基酯和由酰胺碱介导的烷基卤，酰氯或氯甲酸烷基酯制备。这种高效温和的方法可耐受各种官能团，并以良好或极好的收率提供α，α-二取代的β-炔基酯。该方法特别适合于合成1，n-烯炔或1，n-二炔（n> 4）。1,5-烯炔的亲电环化产生高度官能化的γ-碘内酯，而其铂催化的环异构化产生1,3-环己二烯。
• Copper-Catalyzed Synthesis of 2,4-Disubstituted Allenoates from α-Diazoesters
  作者：Matthew Hassink、Xiaozhong Liu、Joseph M. Fox

  DOI：10.1021/ol2006242

  日期：2011.5.6

  α-substituted-α-diazoesters with terminal alkynes to give substituted allenoates is described. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.

  描述了一种用于将 α-取代-α-重氮酯与末端炔烃偶联以产生取代的烯丙酸酯的 Cu 催化方法。开发选择性方法的关键是认识到外来碱催化异构化形成烯丙酸酯产物。提出了一种合理的机制，部分基于反对将 Cu(I)-乙炔化物作为低价中间体的机制的证据。
• Michael Addition of Allenoates to Electron-Deficient Olefins: Facile Synthesis of 2-Alkynyl-Substituted Glutaric Acid Derivatives
  作者：Le-Ping Liu、Bo Xu、Gerald B. Hammond

  DOI：10.1021/ol801411b

  日期：2008.9.1

  A Michael addition of allenoates to electron-deficient olefins was mediated efficiently by a catalytic amount of commercial tetra-n-butylammonium fluoride (TBAF) under mild conditions. And 2-alkynyl substituted glutaric acid derivatives, which may be potential building blocks in organic synthesis, were obtained in good to excellent yields from these reactions. The mechanism for the Michael addition

  在温和条件下，催化量的商业化四正丁基氟化铵（TBAF）有效介导了烯丙酸酯向缺电子烯烃的迈克尔加成反应。从这些反应中可以很好地获得2-炔基取代的戊二酸衍生物，它们可能是有机合成的潜在组成部分。迈克尔加成反应的机理可能涉及炔属烯酸酯中间体的形成。
• [EN] SYNTHESIS OF STABLE ORGANOGOLD COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] SYNTHÈSE DE COMPOSÉS ORGANO-OR STABLES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：HAMMOND GERALD B

  公开号：WO2010062846A1

  公开（公告）日：2010-06-03

  Disclosed herein are novel gold containing compounds and methods of synthesis and use thereof. The novel compounds are very stable. The stability of the compounds allows for their use in methods of treating cancer cells. Disclosed herein are examples of the use of the compounds to inhibit growth of cancer cell lines. The utility of the compounds disclosed herein is a method of treating cancer cells in which a therapeutically effective amount of a compound is administered.

  本文揭示了一种新型含金化合物及其合成和使用方法。这些新型化合物非常稳定。化合物的稳定性使其可以用于治疗癌细胞的方法。本文披露了利用这些化合物抑制癌细胞系生长的示例。本文披露的化合物的实用性是一种治疗癌细胞的方法，其中向患者施用治疗有效量的化合物。
• Highly Efficient and Tunable Synthesis of Dioxabicyclo[4.2.1] Ketals and Tetrahydropyrans via Gold-Catalyzed Cycloisomerization of 2-Alkynyl-1,5-diols
  作者：Le-Ping Liu、Gerald B. Hammond

  DOI：10.1021/ol902215n

  日期：2009.11.5

  A highly efficient gold(I) chloride catalyzed cycloisomerization of 2-alkynyl-1,5-diol (1) to dioxabicyclo[4.2.1] ketal (2) and its further transformation to tetrahydropyran (3) are reported. The diol is readily obtained by the reduction of 2-alkynyl-substituted glutarates, isolated from the Michael addition of allenoates to methyl acrylate. These reactions proceeded smoothly under very mild conditions

  报道了一种高效的金（I）氯化金催化的2-炔基-1,5-二醇（1）向二氧杂双环[4.2.1]缩酮（2）的环异构化及其进一步转化为四氢吡喃（3）。二醇可通过还原2-炔基取代的戊二酸酯而容易地获得，所述2-炔基取代的戊二酸酯是从烯丙酸酯的迈克尔加成到丙烯酸甲酯中分离的。这些反应在非常温和的条件下顺利进行。提出了从相应的缩酮形成所述四氢吡喃的合理机理。