methyl 2-butyl-4-methylhexa-2,3,5-trienoate | 1264272-18-5

• 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: methyl 2-butyl-4-methylhexa-2,3,5-trienoate
• CAS: 1264272-18-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: LMNYRVBWEKFICN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 正丁基锂 、 hydroxycarbene 、 溴化镁 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 (Z)-methyl 4-methyldec-3-en-5-ynoate 、 methyl 2-butyl-4-methylhexa-2,3,5-trienoate
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q

文献信息

• Regio- and Stereoselective Synthesis of 2,3,5-Trienoates by Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Carbonates
  作者：Ezgi Şule Karagöz、Melih Kuş、Gürkan Eray Akpınar、Levent Artok

  DOI：10.1021/jo5014993

  日期：2014.10.3

  Palladium-catalyzed carbonylation of 2,4-enyne carbonates in an alcohol and under balloon pressure of CO proceeds through 1,5-substitution to yield (E)-2,3,5-trienoates. The olefin geometry of the substrate is important to control the overall stereochemistry of this alkoxycarbonylation method. The reaction proceeds through successive formation of π-allylpalladium with an R3 group oriented syn and σ-allenyl

  钯在醇中和在CO的气球压力下催化2,4-烯炔碳酸酯的羰基化反应通过1,5-取代而生成（E）-2,3,5-三烯酸酯。底物的烯烃几何形状对于控制这种烷氧羰基化方法的整体立体化学很重要。该反应通过依次形成具有R 3基团的顺式和σ-烯基钯配合物的π-烯丙基钯来进行。