2-(4-Tolyl)-1,4-pentadiene | 134261-81-7

• 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: 2-(4-Tolyl)-1,4-pentadiene
• 英文别名: 2-(4-methylphenyl)-1,4-pentadiene；1-Methyl-4-penta-1,4-dien-2-ylbenzene
• CAS: 134261-81-7
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: WNGQDRHQKUPXMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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

• 作为反应物：
  描述：

  氨基二苯甲烷 、 2-(4-Tolyl)-1,4-pentadiene 在 C₃₁H₅₁N₂ScSi₂ 、 三苯碳四(五氟苯基)硼酸盐 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以68%的产率得到
  参考文献：
  名称：

  Synthesis of Tetrahydroquinolines by Scandium-Catalyzed [3 + 3] Annulation of Anilines with Allenes and Dienes

  摘要：

  DOI：

  10.1021/acscatal.1c04657
• 作为产物：
  描述：

  3-溴丙烯 、 2-溴-4'-甲基苯乙酮 在 三氢化钐 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 以83%的产率得到2-(4-Tolyl)-1,4-pentadiene
  参考文献：
  名称：

  烯丙基sa溴化物作为格氏试剂和单电子转移试剂在二元和三元一锅法合成中的应用

  摘要：

  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。

  DOI：

  10.1002/chem.200901927

文献信息

• Regioselective allylgallation of terminal alkynes
  作者：Phil Ho Lee、Yunkiu Heo、Dong Seomoon、Sundae Kim、Kooyeon Lee

  DOI：10.1039/b417975g

  日期：——

  The reactions of terminal alkynes with allylgallium reagents generated in situ from gallium and allyl bromides gave the corresponding 1,4-dienes in good yield via Markovnikov addition in THF at 70 °C.

  终端炔烃与现场生成的烯丙基镓试剂（由镓和烯丙基溴化物反应生成）在THF中于70°C进行Markovnikov加成反应，得到相应的1,4-二烯，产率良好。
• trans-Allylstannylation of certain acetylenes catalysed by ZrCl4
  作者：Naoki Asao、Yasuhisa Matsukawa、Yoshinori Yamamoto

  DOI：10.1039/cc9960001513

  日期：——

  The trans-allylstannylation of simple acetylenes 1 is catalysed by ZrCl4 to produce the corresponding alkenylstannanes 3 (or alkenes 4 upon protonolysis of the C–Sn bond) in a regio- and stereo-selective manner.

  通过 ZrCl4 催化简单乙炔 1 的反式烯丙基锡烷化反应，以区域和立体选择性的方式生成相应的烯基锡烷 3（或 C-Sn 键质子裂解后生成的烯烃 4）。
• 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.
• Allylation of Unactivated and/or Functionalized Alkynes with Allylindiums
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo9701041

  日期：1997.4.1
• Allyl- and Benzylindium Reagents. Carboindation of Carbon−Carbon and Carbon−Nitrogen Triple Bonds
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo990160x

  日期：1999.5.1

  The reaction of unactivated simple terminal alkynes 1 with allylindiums in THF proceeded smoothly to give the corresponding allylation products 2 in good to high yields. This result is in marked contrast to that of the reaction carried out in DMF, where the allylation of unactivated alkynes was very sluggish. The allylic group of the reagent was attached to the internal carbon of the triple. bond, and indium was attached to the less substituted terminal carbon, except for the case of TMS substituted acetylenes 1j and 1k in which the allyl group went to the less substituted carbon of the triple band. The reaction of unactivated simple terminal and certain internal acetylenes with benzylindium in THF proceeded smoothly to afford the corresponding benzylation products 18 in good to high yields. The benzyl group was attached to the less substituted unhindered carbon of the triple bond, and indium was attached to the more sterically congested carbon. The reaction of activated nitriles 3 with allylindiums in THF at 70 degrees C gave the corresponding allylation-enamination products 4 in high to excellent yields. This reaction provides a useful method for the synthesis of highly functionalized enamines, which are not easily available via conventional methods. The mechanisms on the above three indation reactions are discussed.