2-(4'-Methoxyphenyl)-1,4-pentadien | 60573-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4'-Methoxyphenyl)-1,4-pentadien
• 英文别名: 2-(4-methoxyphenyl)-1,4-pentadiene；1-Methoxy-4-penta-1,4-dien-2-ylbenzene
• CAS: 60573-62-8
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: YYSSPYLHWLOOMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4'-Methoxyphenyl)-1,4-pentadien 、 1-萘胺 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60%的产率得到C₂₂H₂₃NO
  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：

  1-(2,2-dichlorovinyl)-4-methoxybenzene 在 indium 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 2-(4'-Methoxyphenyl)-1,4-pentadien
  参考文献：
  名称：

  Allyl- and Benzylindium Reagents. Carboindation of Carbon−Carbon and Carbon−Nitrogen Triple Bonds

  摘要：

  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.

  DOI：

  10.1021/jo990160x

文献信息

• Catalytic Anti-Markovnikov Hydroallylation of Terminal and Functionalized Internal Alkynes: Synthesis of Skipped Dienes and Trisubstituted Alkenes
  作者：Melrose Mailig、Avijit Hazra、Megan K. Armstrong、Gojko Lalic

  DOI：10.1021/jacs.7b02104

  日期：2017.5.24

  and functionalized internal alkynes. In this article, we describe the development of the reaction, exploration of the substrate scope, and a study of the reaction mechanism. Synthesis of skipped dienes through the hydroallylation of terminal alkyl and aryl alkynes with simple allyl phosphates and 2-substituted allyl phosphates is described. The hydroallylation of functionalized internal alkynes leads

  我们已经开发了末端和功能化的内部炔烃的催化反马尔科夫尼科夫水解反应。在本文中，我们描述了反应的发展、底物范围的探索以及反应机理的研究。描述了通过末端烷基和芳基炔烃与简单的磷酸烯丙酯和 2-取代的磷酸烯丙酯的水解反应合成跳过的二烯。官能化的内部炔烃的水解导致形成含有三取代烯烃的跳跃二烯。我们证明内部炔烃的水解可用于复杂三取代烯烃的区域选择性和非对映选择性合成。提出了加氢烯丙基化反应的机理，并为催化循环的关键步骤提供了实验证据。化学计量实验证明了锂醇盐在反应的碳-碳键形成步骤中的意外作用。对内部炔烃的氢铜反应的研究提供了对烯基铜中间体的结构、稳定性和反应性的新见解，以及对内部炔烃反应中区域选择性来源的见解。
• 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。
• Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction
  作者：Sayuri Hayashi、Koji Hirano、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1016/j.jorganchem.2006.08.047

  日期：2007.1

  reagent and gallium trichloride, bulky homoallyl alcohols undergo gallium-mediated retro-allylation reaction to provide σ-allylgallium reagents. The σ-allylgallium reagents generated were applied to carbonyl allylation. The retro-allylation reaction generates (Z)- and (E)-σ-crotylgalliums stereospecifically, starting from erythro- and threo-homoallyl alcohols, respectively. The stereochemically defined

  公开了一种用于制备和控制动态σ-烯丙基镓的新方法。用格氏试剂和三氯化镓处理后，大体积的均烯丙基醇经历镓介导的逆烯丙基化反应，以提供σ-烯丙基镓试剂。将产生的σ-烯丙基镓试剂应用于羰基烯丙基化。逆向烯丙基化反应分别分别从赤型和苏型烯丙基醇开始立体定向地生成（Z）-和（E）-σ-巴豆基镓。立体化学定义的巴豆基镓试剂实现了醛的立体选择性烯丙基化。还描述了炔烃与通过逆烯丙基化制备的烯丙基镓试剂的烯丙基镓化反应。
• 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。
• Allylgallation reaction of carbon–carbon triple bonds with allylsilanes and GaCl3
  作者：Masahiko Yamaguchi、Takayuki Sotokawa、Masahiro Hirama

  DOI：10.1039/a700552k

  日期：——

  Treatment of alkynes with allyltrimethylsilanes in the presence of GaCl 3 gives 1,4-dienes via allylgallation.

  在GaCl₃存在下，炔烃与 allyltrimethylsilanes 反应生成1,4-二烯，过程称为 allylgallation。