(Z)-penta-1,3-dienylbenzene | 39491-56-0

• 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: (Z)-penta-1,3-dienylbenzene
• 英文别名: [(1Z,3Z)-penta-1,3-dienyl]benzene
• CAS: 39491-56-0
• 化学式: C₁₁H₁₂
• 分子量: 144.216
• InChiKey: BCRJHHFLBOQAMG-FKVZMRKJSA-N

物化性质

• 沸点：
  228.8±7.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-phenyl-1,3-pentadiene 以 正己烷 为溶剂， 反应 1.0h， 生成 (1Z,3E)-penta-1,3-dien-1-ylbenzene 、 (Z)-penta-1,3-dienylbenzene
  参考文献：
  名称：

  Roth, Wolfgang R.; Rekowski, Volker; Boerner, Sabine, Liebigs Annalen, 1996, # 3, p. 409 - 430

  摘要：

  DOI：

文献信息

• Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts
  作者：S. M. A. Hakim Siddiki、Abeda Sultana Touchy、Kenichi Kon、Ken-ichi Shimizu

  DOI：10.1002/chem.201505109

  日期：2016.4.18

  catalysts for the direct Julia olefination of alcohols in the presence of sulfones and KOtBu under oxidant‐free conditions. Primary alcohols, including aryl, aliphatic, allyl, and heterocyclic alcohols, underwent olefination with dimethyl sulfone and aryl alkyl sulfones to give terminal and internal olefins, respectively. Secondary alcohols underwent methylenation with dimethyl sulfone. Under 2.5 bar

  发现在无氧化剂条件下，在砜和KO t Bu存在的情况下，碳负载的Pt纳米颗粒（Pt / C）是有效的多相催化剂，可直接用于醇的Julia烯化反应。伯醇，包括芳基，脂族，烯丙基和杂环醇，分别与二甲基砜和芳基烷基砜进行烯烃化反应，分别得到末端烯烃和内部烯烃。仲醇与二甲基砜进行亚甲基化。在2.5 bar H 2下，相同的反应体系对于将醇OH基团转化为烷基基团是有效的。末端烯烃化系统的结构和机理研究表明Pt 0Pt金属颗粒上的两个位点是限制醇脱氢速率的原因，而KO t Bu可能会使砜试剂脱质子。Pt / C催化剂在烯化后可重复使用，与以前报道的方法相比，该方法显示出更高的周转数（TON）和更宽的底物范围，这证明了本方法的高催化效率。
• A synthesis of conjugated dienes from aromatic, five-membered heterocycles
  作者：Ernest Wenkert、Michael H. Leftin、Enrique L. Michelotti

  DOI：10.1039/c39840000617

  日期：——

  Reaction of furan, thiophene, selenophene, and tellurophene as well as 2-methyl and 2,5-dimethyl derivatives of the first two heterocycles with phenyl-, methyl-, and n-butyl-magnesium bromides in the presence of ligated nickel dichloride are shown to yield buta-1,3-dienes mostly with retention of configuration.

  在连接的二氯化镍存在下，呋喃，噻吩，硒基和碲二苯以及前两个杂环的2-甲基和2,5-二甲基衍生物与苯基，甲基和正丁基溴化镁的反应是显示出产生大部分保留构型的buta-1,3-二烯。
• 2-Allylisourea as a Starting Material for Palladium-Catalyzed Wittig-Type Allylidenation of Aldehydes
  作者：Yoshio Inoue、Masanori Toyofuku、Harukichi Hashimoto

  DOI：10.1246/bcsj.59.1279

  日期：1986.4

  2-Allylic-substituted isoureas underwent Wittig-type allylidenation of aldehydes in the presence of triphenylphosphine and 2 mol% of [Pd(PPh3)3] to give the corresponding conjugated olefins in tolerable to good yields.

  在三苯基膦和 2 mol% [Pd(PPh3)3]的存在下，2-烯丙基取代的异脲类发生了醛的 Wittig 型烯丙叉化反应，得到了相应的共轭烯烃，收率从可接受到良好。
• Stereochemistry of Carbenic 1,2-Vinyl Shifts
  作者：Wolfgang Kirmse、Siegfried Kopannia

  DOI：10.1021/jo971691t

  日期：1998.2.1

  Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R'CH=CHC(Ph)=CR2, were found to predominate over gamma-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R' = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R' = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point, to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).
• WENKERT, E.;LEFTIN, M. H.;MICHELOTTI, E. L., J. CHEM. SOC. CHEM. COMMUN., 1984, N 9, 617-618
  作者：WENKERT, E.、LEFTIN, M. H.、MICHELOTTI, E. L.

  DOI：——

  日期：——