methyl (2E,7E)-9-oxo-2,7-decadienoate | 136202-44-3

• 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: methyl (2E,7E)-9-oxo-2,7-decadienoate
• 英文别名: Methyl 9-oxo-2(E),7(E)-decadienoate；methyl (2E,7E)-9-oxoundeca-2,7-dienoate；methyl (2E,7E)-9-oxodeca-2,7-dienoate
• CAS: 136202-44-3
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: GNJKKVBQWQUREA-CDJQDVQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E,7E)-9-oxo-2,7-decadienoate 在 偶氮二异丁腈 、 溴 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以86%的产率得到Methyl 2-<2-(1-bromo-2-oxopropyl)cyclopentyl>ethanoate
  参考文献：
  名称：

  Enholm, Eric J.; Kinter, Kevin S., Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7784 - 7785

  摘要：

  DOI：
• 作为产物：
  描述：

  戊二醛 以 二氯甲烷 为溶剂， 生成 methyl (2E,7E)-9-oxo-2,7-decadienoate
  参考文献：
  名称：

  Enholm, Eric J.; Kinter, Kevin S., Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7784 - 7785

  摘要：

  DOI：

文献信息

• Concise synthesis of oxacyclic compounds using highly discriminative two-way transformations of α,β-unsaturated esters in the presence of enones
  作者：Kenta Morita、Reiya Ohta、Hiroshi Aoyama、Kenzo Yahata、Mitsuhiro Arisawa、Hiromichi Fujioka

  DOI：10.1039/c7cc03287k

  日期：——

  Highly discriminative transformation of α,β-unsaturated esters in the presence of enones using two types of phosphonium salts, and their application to the synthesis of oxacyclic compounds in six steps in one pot have been achieved.

  使用两种类型的phospho盐，在烯酮存在下对α，β-不饱和酯进行了高判别转化，并将其应用于一锅六步合成乙二环化合物。
• Copper-Catalyzed Enantioselective Intramolecular Conjugate Addition/Trapping Reactions: Synthesis of Cyclic Compounds with Multichiral Centers
  作者：Kangying Li、Alexandre Alexakis

  DOI：10.1002/chem.200601327

  日期：2007.4.27

  The Cu-catalyzed enantioselective conjugate addition of dialkylzinc to bis-alpha,beta-unsaturated carbonyl compounds followed by the intramolecular trapping of the zinc enolate in the presence of chiral phosphoramidite ligands was investigated. Cyclic and heterocyclic compounds with multichiral centers were formed as a mixture of two diastereomers with excellent diastereoselectivities (up to 99:1)

  研究了铜催化的双烷基锌向双-α，β-不饱和羰基化合物的对映选择性共轭加成反应，然后在手性亚磷酰胺配体的存在下分子内捕获烯醇酸锌。具有多手性中心的环状和杂环化合物是两种非对映异构体的混合物，具有优异的非对映选择性（最高99：1）和对映选择性（最高94％ee，ee =对映体过量）。立体化学被确定为主要产品是反式，反式和次要产品是反式，顺式。通过与反式-3-壬烯-2-酮和Et（2）Zn衍生的类似加合物或通过将Me（2）Zn共轭加到反式-1-中获得的加合物进行比较，确定了环状化合物的绝对构型苯基-非-2-en-1-一个。
• The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction:  Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts
  作者：Scott A. Frank、Dustin J. Mergott、William R. Roush

  DOI：10.1021/ja017123j

  日期：2002.3.1

  intramolecular Morita-Baylis-Hillman reaction for the synthesis of functionalized cyclopentenes and cyclohexenes is described. The reaction involves the trialkyphosphine-catalyzed cyclization of 1,6- or 1,7-diactivated 1,5-hexadienes or 1,6-heptadienes, containing carboxyaldehyde, methyl ketone, or methoxycarbonyl as the olefin activating groups. A representative example of this reaction is the Me(3)P-catalyzed

  描述了用于合成功能化环戊烯和环己烯的乙烯基分子内 Morita-Baylis-Hillman 反应的发展。该反应涉及三烷基膦催化的 1,6- 或 1,7- 双活化的 1,5-己二烯或 1,6-庚二烯的环化反应，其中含有甲醛、甲基酮或甲氧基羰基作为烯烃活化基团。该反应的一个代表性例子是 Me(3)P 催化的 1a 在叔戊醇中的环化，它以 95% 的产率和 97:3 的区域选择性提供取代的环戊烯 2a。
• Copper catalyzed tandem asymmetric conjugate addition–cyclization reaction in the presence of chiral phosphoramidite ligands
  作者：Kangying Li、Alexandre Alexakis

  DOI：10.1016/j.tetlet.2005.09.065

  日期：2005.11

  Copper-catalyzed intramolecular conjugate addition-cyclization in the presence of chiral phosphoramidite ligands was described. Cyclic products with multiple chiral centers were obtained with up to 93:7 diastereomeric ratio and 94% ee. (c) 2005 Elsevier Ltd. All rights reserved.
• Cyclization Reactions of Allylic O-Stannyl Ketyls
  作者：Eric J. Enholm、Kevin S. Kinter

  DOI：10.1021/jo00120a031

  日期：1995.7

  This is a summary of an investigation of the tributyltin hydride-induced cyclization reactions of unsaturated ketones with electronically deficient olefins. This reaction was initiated by an O-stannyl ketyl formed by the addition of a tributyltin radical to a carbonyl, which has both anionic and radical character. The intramolecular coupling produced functionalized cyclopentanes, bearing two synthetically useful carbon appendages. An activating or electron-withdrawing function on the alkene was essential to the cyclization. A dilution study revealed that excellent anti stereoselectivities (>50:1) could be achieved, and this was attributed to a reversible cyclization. Another goal of this study was to separate the radical reactivity from the anionic reactivity of the O-stannyl ketyl by the participation of labile functional groups and external electrophiles. The presence of minor products and enolate-trapping studies demonstrated that the anionic character of the ketyl could be utilized in the form of a tin enolate. This work represents the first free radical- and reagent-based approach to the study of the intramolecular hydrodimerization of activated alkenes.