1-(4-(2-methylallyl)phenyl)ethanone | 878812-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(2-methylallyl)phenyl)ethanone
• 英文别名: 1-[4-(2-Methyl-2-propen-1-yl)phenyl]ethanone；1-[4-(2-methylprop-2-enyl)phenyl]ethanone
• CAS: 878812-97-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: ZXOGBWCADUUIOM-UHFFFAOYSA-N

物化性质

• 沸点：
  274.5±19.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基-2-丙烯基乙酸酯 、 4-碘代苯乙酮 在 N-乙基-2-吡咯烷酮 、 氯化镍二甲氧基乙烷 、 4,4',4''-三叔丁基2,2',6'2''-曲吡啶 、 锌 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到1-(4-(2-methylallyl)phenyl)ethanone
  参考文献：
  名称：

  Selective Cross-Coupling of Organic Halides with Allylic Acetates

  摘要：

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

  DOI：

  10.1021/jo302086g

文献信息

• Photoinduced Cross-Coupling of Aryl Iodides with Alkenes
  作者：Yuliang Liu、Haoyu Li、Shunsuke Chiba

  DOI：10.1021/acs.orglett.0c03935

  日期：2021.1.15

  A protocol for photoinduced cross-coupling of aryl iodides having polar π-functional groups or elongated π-conjugation with alkenes has been developed. The radical cascade mechanism involving generation of aryl radicals via C–I bond homolysis of photoexcited aryl iodides and their subsequent addition to alkenes is proposed. The method enables iodide-selective cross-coupling over other halogen leaving

  已经开发出用于光诱导的具有极性π-官能团的芳基碘的交叉偶联或延长的与烯烃的π-共轭的方案。提出了一种自由基级联机制，涉及通过光激发的芳基碘化物的C–I键均质化及其随后添加到烯烃中的芳基自由基的产生。该方法使得碘化物与其他卤素离去基团的选择性碘交叉偶联具有在芳烃和烯烃基团上的官能团相容性。
• Palladium-Catalyzed Stereo- and Regiospecific Allylation of Aryl Halides with Homoallyl Alcohols via Retro-Allylation:  Selective Generation and Use of σ-Allylpalladium
  作者：Sayuri Hayashi、Koji Hirano、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ja058055u

  日期：2006.2.1

  Treatment of tertiary homoallyl alcohol with aryl halide under palladium catalysis resulted in the transfer of the allyl moiety of the homoallyl alcohol to aryl halide and yielded the corresponding cross-coupling product stereo- and regiospecifically. The transfer process includes retro-allylation, which proceeds via a conformationally regulated six-membered transition state. The retro-allylation can

  在钯催化下用芳基卤处理叔高烯丙醇导致高烯丙醇的烯丙基部分转移到芳基卤，并产生相应的立体和区域特异性交叉偶联产物。转移过程包括逆烯丙基化，其通过构象调节的六元过渡态进行。逆烯丙基化可被视为一种立体和区域特异性制备σ-烯丙基钯的方法。
• Electroreductive Nickel-Catalyzed Allylation of Aryl Chlorides
  作者：Xin Fu、Tingting Ran、Yu Zhou、Jie Liu

  DOI：10.1021/acs.joc.2c02926

  日期：2023.5.5

  allylation via electrochemical promoted Ni-catalyzed reductive carbon–carbon bond formation. Readily available (hetero)aryl chlorides with a variety of allylic sulfones are used as electrophiles in this electroreductive coupling. This Ni-catalyzed modular approach displays generally good functional group tolerance and broad substrate scope. This reaction allows a series of allylic compounds to be created

  在此，我们报告了一种通过电化学促进的镍催化的还原性碳-碳键形成的简便有效的烯丙基化反应。在这种电还原偶联中，使用现成的（杂）芳基氯和各种烯丙基砜作为亲电子试剂。这种镍催化的模块化方法通常显示出良好的官能团耐受性和广泛的底物范围。该反应可以生成一系列烯丙基化合物，包括几种结构复杂的天然产物和药物基序。
• Selective Cross-Coupling of Organic Halides with Allylic Acetates
  作者：Lukiana L. Anka-Lufford、Michael R. Prinsell、Daniel J. Weix

  DOI：10.1021/jo302086g

  日期：2012.11.16

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.