(2E,4E)-2-methyl-5-phenylpenta-2,4-dien-1-ol | 54355-96-3

• 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: (2E,4E)-2-methyl-5-phenylpenta-2,4-dien-1-ol
• CAS: 54355-96-3
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: FEGUPOQVEDAZMG-MPEOSAONSA-N

物化性质

• 沸点：
  297.8±9.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2-methyl-5-phenylpenta-2,4-dien-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 25.0~140.0 ℃ 、5.07 MPa 条件下， 反应 3.0h， 生成 2-Acetoxy-4-methylbiphenyl
  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
• 作为产物：
  描述：

  ethyl (2E,4E)-2-methyl-5-phenylpenta-2,4-dienoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2E,4E)-2-methyl-5-phenylpenta-2,4-dien-1-ol
  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

• Synthesis of <i>Z</i>- or <i>E</i>-Trisubstituted Allylic Alcohols and Ethers by Kinetically Controlled Cross-Metathesis with a Ru Catechothiolate Complex
  作者：Chaofan Xu、Zhenxing Liu、Sebastian Torker、Xiao Shen、Dongmin Xu、Amir H. Hoveyda

  DOI：10.1021/jacs.7b10010

  日期：2017.11.8

  kinetically controlled cross-metathesis reactions that generate Z- or E-trisubstituted alkenes are disclosed. Transformations are catalyzed by ≤6.0 mol % of a Ru catechothiolate complex and afford trisubstituted allylic alcohols and ethers in up to 81% yield and >98% stereoisomeric purity. The method has considerable scope, as olefins containing an alcohol, an aldehyde, an epoxide, a carboxylic acid, or an

  公开了产生Z-或E-三取代烯烃的动力学控制的交叉复分解反应的第一个例子。转化由≤6.0 mol% 的儿茶酚硫醇络合物催化，并以高达 81% 的产率和 >98% 的立体异构纯度提供三取代的烯丙醇和醚。该方法具有相当大的范围，因为可以使用含有醇、醛、环氧化物、羧酸或烯基的烯烃。基于 DFT 研究，提供了解释效率和立体化学控制中观察到的水平和趋势的机械模型。
• Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols
  作者：James M. Takacs、Xun-tian Jiang、Alexei P. Leonov

  DOI：10.1016/s1268-7731(03)00074-2

  日期：2003.9

  The triethylborane-promoted and palladium-catalyzed reactions of 2,4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)(2) with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)(2) and Ph3P affords in the catalyzed reactions of dienyl acetates. (C) 2003 Elsevier Ltd. All rights reserved.
• Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates
  作者：Youichi Ishii、Chao Gao、Wen Xiang Xu、Masakazu Iwasaki、Masanobu Hidai

  DOI：10.1021/jo00076a051

  日期：1993.11

  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.