(2E,4E)-5-(furan-2-yl)penta-2,4-dien-1-yl acetate | 143816-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2E,4E)-5-(furan-2-yl)penta-2,4-dien-1-yl acetate
• 英文别名: (2E,4E)-5-(2-Furyl)-2,4-pentadienyl acetate；[(2E,4E)-5-(furan-2-yl)penta-2,4-dienyl] acetate
• CAS: 143816-08-4；135449-04-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: HELKSPNRNQEKJQ-PIXFVPMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (2E,4E)-5-(furan-2-yl)penta-2,4-dien-1-yl 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57%的产率得到2-(2-呋喃基)苯基乙酸酯
  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：

  (2E,4E)-ethyl 5-(furan-2-yl)penta-2,4-dienoate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 (2E,4E)-5-(furan-2-yl)penta-2,4-dien-1-yl 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

• Pd(II)-Catalyzed Dehydrogenative Olefination of Vinylic C–H Bonds with Allylic Esters: General and Selective Access to Linear 1,3-Butadienes
  作者：Yuexia Zhang、Zili Cui、Zejiang Li、Zhong-Quan Liu

  DOI：10.1021/ol300442w

  日期：2012.4.6

  dienes by Pd(II)-catalyzed direct olefination of unactivated alkenes with allylic esters and acrylates via vinylic C–H activation. Various aryl and heteroaryl alkenes as well as aliphatic alkenes all give the desired linear 1,3-butadienes with retention of the traditional leaving groups such as OAc and other carboxylic acid ester groups.

  这项工作展示了一种通用而有效的方法，该方法通过Pd（II）催化未活化烯烃与烯丙基酯和丙烯酸酯的乙烯基C–H活化而被直接活化，以制备共轭二烯。各种芳基和杂芳基烯烃以及脂族烯烃都得到所需的直链1，3-丁二烯，同时保留了传统的离去基团，如OAc和其他羧酸酯基团。
• 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.