(E)-2-phenyl-1-methyl-1,4-pentadiene | 14255-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-phenyl-1-methyl-1,4-pentadiene
• 英文别名: (E)-hexa-2,5-dien-3-ylbenzene；(Z)-4-Phenyl-1,4-hexadiene；trans-4-Phenylhexa-1,4-dien；[(2E)-hexa-2,5-dien-3-yl]benzene
• CAS: 14255-25-5
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: NDUWAVKSSGDGEQ-NYYWCZLTSA-N

物化性质

• 沸点：
  225.6±15.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯丙酮乙烷-1,2-二基二硫代缩醛 、 3-溴丙烯 在 1,2-双(二苯基膦)乙烷氯化镍 、 magnesium 作用下， 生成 (E)-2-phenyl-1-methyl-1,4-pentadiene
  参考文献：
  名称：

  Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism

  摘要：

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.

  DOI：

  10.1021/jo00012a043

文献信息

• Applications of Allylsamarium Bromide as a Grignard Reagent and a Single-Electron Transfer Reagent in the One-Pot Synthesis of Dienes and Trienes
  作者：Yuanyuan Hu、Tao Zhao、Songlin Zhang

  DOI：10.1002/chem.200901927

  日期：2010.2.1

  reagent and a single‐electron transfer (SET) reagent in the reaction of α‐halo, γ‐halo‐α,β‐unsaturated ketones and esters with allylsamarium bromide is reported for the first time in this paper. From a synthetic point of view, a general, efficient and experimentally simple one‐pot method for the preparation of 1,4‐dienes and trienes is developed. A possible mechanism of the transformation is proposed.

  首次报道了烯丙基溴化溴作为亲核试剂和单电子转移（SET）试剂在α-卤代，γ-卤代-α，β-不饱和酮和酯与烯丙基溴化reaction的反应中的用途在本文中。从综合的角度出发，开发了一种通用，高效且实验简单的一锅法制备1,4-二烯和三烯的方法。提出了一种可能的转化机制。
• Nickel-Catalyzed Allylic Substitution of Simple Alkenes
  作者：Ryosuke Matsubara、Timothy F. Jamison

  DOI：10.1021/ja101186p

  日期：2010.5.26

  Nickel-catalyzed intermolecular allylic substitution of simple alkenes (ethylene and alpha olefins) is described. This method is the first catalytic intermolecular process for direct allylation of nonconjugated, nonstrained simple alkenes. Catalyst loadings as low as 2.5 mol % Ni afford the desired product in high yield in both gram-scale and smaller scale coupling reactions.
• MITSUDO TAKE-AKI; KADOKURA MATORU; WATANABE YOSHIHISA, J. ORG. CHEM., 52,(1987) N 9, 1695-1699
  作者：MITSUDO TAKE-AKI、 KADOKURA MATORU、 WATANABE YOSHIHISA

  DOI：——

  日期：——
• Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism
  作者：Zhi Jie Ni、Nai Wen Mei、Xian Shi、Yih Ling Tzeng、Maw Cherng Wang、Tien Yau Luh

  DOI：10.1021/jo00012a043

  日期：1991.6

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.