trans,trans,trans-undeca-2,4,6-trienyl acetate | 135449-06-8

• 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: trans,trans,trans-undeca-2,4,6-trienyl acetate
• 英文别名: (2E,4E,6E)-2,4,6-Undecatrienyl acetate；[(2E,4E,6E)-undeca-2,4,6-trienyl] acetate
• CAS: 135449-06-8
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: BOZOUKGCVZIUOZ-OBWVEWQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 trans,trans,trans-undeca-2,4,6-trienyl acetate 在 bis-triphenylphosphine-palladium(II) chloride 、 乙酸酐 、 三乙胺 作用下， 以 苯 为溶剂， 140.0 ℃ 、5.07 MPa 条件下， 反应 3.0h， 以52%的产率得到o-(hex-1-enyl)phenyl acetate
  参考文献：
  名称：

  Novel synthesis of phenol derivatives by palladium-catalysed cyclocarbonylation of penta-2,4-dienyl acetates

  摘要：

  在 NEt3 和 Ac2O 存在下，钯催化的戊-2,4-二烯乙酸酯环羰基化反应可选择性地生成苯基乙酸酯，且收率高。

  DOI：

  10.1039/c39910000695
• 作为产物：
  描述：

  (E,E)-2,4-壬二烯醛 在 lithium aluminium tetrahydride 、 sodium ethanolate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 trans,trans,trans-undeca-2,4,6-trienyl acetate
  参考文献：
  名称：

  Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates

  摘要：

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.

  DOI：

  10.1021/jo00076a051

文献信息

• Palladium- and platinum-catalyzed cyclocarbonylation reactions of substituted allyl acetates
  作者：Youichi Ishii、Masanobu Hidai

  DOI：10.1016/0022-328x(92)83237-c

  日期：1992.4

  The scope and limitation of novel palladium- and platinum-catalyzed cyclocarbonylation reactions of 3-arylallyl and 2,4-pentadienyl acetates are described. The detailed mechanism of these reactions is also discussed.