3-(2,4,6-trimethoxyphenyl)cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2,4,6-trimethoxyphenyl)cyclohexanone
• 英文别名: 3-(2,4,6-Trimethoxyphenyl)cyclohexan-1-one；3-(2,4,6-trimethoxyphenyl)cyclohexan-1-one
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: UNXRPMPVWXMQEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 1,3,5-三甲氧基苯 在 gold(III) chloride 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 以80%的产率得到3-(2,4,6-trimethoxyphenyl)cyclohexanone
  参考文献：
  名称：

  金（III）催化的杂环加成至缺电子的烯烃和炔烃

  摘要：

  此处报道了金（III）催化的不同烯烃的加氢芳基化反应。AuCl 3是出色的催化剂，可在温和条件下介导各种杂环与缺电子的烯烃和炔烃之间的反应。这种基于金（III）的方法可以耐受不同的官能团，例如醛，羧酸，腈，并且效率很高。我们已经表明，其中一些反应在室温下可在数分钟内完成。

  DOI：

  10.1016/j.jorganchem.2005.03.009

文献信息

• Addition of heterocycles to electron deficient olefins and alkynes catalyzed by gold(III)
  作者：Zigang Li、Zhangjie Shi、Chuan He

  DOI：10.1016/j.jorganchem.2005.03.009

  日期：2005.11

  A gold(III)-catalyzed hydroarylation of different olefins is reported here. AuCl3 works as an excellent catalyst to mediate reactions between various heterocycles and electron deficient olefins and alkynes under mild conditions. This gold(III)-based method tolerates different functional groups such as aldehyde, carboxylic acid, nitrile, and is highly efficient. We have shown that some of these reactions

  此处报道了金（III）催化的不同烯烃的加氢芳基化反应。AuCl 3是出色的催化剂，可在温和条件下介导各种杂环与缺电子的烯烃和炔烃之间的反应。这种基于金（III）的方法可以耐受不同的官能团，例如醛，羧酸，腈，并且效率很高。我们已经表明，其中一些反应在室温下可在数分钟内完成。
• Solvent-free Brønsted acid-catalyzed Michael addition of nitrogen- and carbon-containing nucleophiles by ultrasound activation
  作者：Xiu-Jiang Du、Zhi-Peng Wang、Yan-Ling Hou、Cheng Zhang、Zheng-Ming Li、Wei-Guang Zhao

  DOI：10.1016/j.tetlet.2013.12.059

  日期：2014.1

  carbon-containing nucleophiles to cyclic enones. Using this conjugate addition reaction, a variety of different nucleophiles can react with a range of cyclic enones in the presence of p-toluenesulfonic acid under solvent-free ultrasound irradiation conditions affording the corresponding C–N or C–C adducts in good to excellent yields. Comparatively, performing the reaction under ultrasound irradiation gives

  已经开发出一种新的方法，用于将含氮和碳的亲核试剂迈克尔加成到环烯酮上。使用这种共轭加成反应，在对甲苯磺酸的存在下，无溶剂超声辐照条件下，多种不同的亲核试剂可以与多种环烯酮反应，从而提供相应的C–N或C–C加合物，且收率良好。 。相比之下，与在高压下进行反应相比，在超声辐射下进行反应可获得更高的产率，更有效且对环境无害。
• Catalytic Conjugate Additions of Nitrogen-, Phosphorus-, and Carbon-Containing Nucleophiles by Amphoteric Vanadyl Triflate
  作者：Yow-Dzer Lin、Jun-Qi Kao、Chien-Tien Chen

  DOI：10.1021/ol702302y

  日期：2007.12.1

  A series of carbamates, amides, N-tosyl amides, (hetero)arenes, and hydrogen phosphines/phosphites has been examined as nucleophiles for (hetero)Michael-type additions to enones and enamides catalyzed by amphoteric vanadyl triflate under mild and neutral conditions. The newly developed C-N, C-P, and C-C bond-formation protocols were carried out smoothly in good to high yields without intervention of any 1,2-additions.
• Efficient Functionalization of Aromatic C−H Bonds Catalyzed by Gold(III) under Mild and Solvent-Free Conditions
  作者：Zhangjie Shi、Chuan He

  DOI：10.1021/jo0497353

  日期：2004.5.1

  A gold(III)-catalyzed carbon-carbon bond formation reaction between arenes and electron-deficient alkynes or alkenes is described. Electron-rich arenes can be efficiently functionalized with the alkyne or alkene substrates. This reaction can be run with neat reactants at ambient temperature. Under the "solventless" conditions, clean product was obtained from a reaction of equal molar amounts of arene and alkyne substrates. The mild conditions and potential tolerance to different functional groups make this method practical for arene functionalization and for constructing complicated molecules. Efficient preparation of various coumarins from aryl alkynoates was demonstrated. Preliminary mechanistic studies were performed to probe the pathway of this reaction.
• A rapid and highly efficient Michael addition of methoxybenzenes and indoles to α,β-unsaturated ketones using BF 3 ·OEt 2 as a catalyst
  作者：A. Swetha、M. Raghavender Reddy、B. Madhu Babu、H.M. Meshram

  DOI：10.1016/j.tetlet.2017.09.016

  日期：2017.11

  An efficient and general protocol is described for the Michael addition of α,β-unsaturated ketones with electron-rich arenes/indoles to give alkylated arenes/indoles under mild reaction condition at room temperature. Shorter reaction time, convenient and good isolated yields are the significant features of this protocol. Moreover, the procedure is environmentally benign in nature and applicable to

  描述了一种有效且通用的方案，用于在室温下在温和的反应条件下，将α，β-不饱和酮与富电子的芳烃/吲哚进行迈克尔加成反应，以生成烷基化的芳烃/吲哚。较短的反应时间，方便的分​​离产率和良好的收率是该方案的重要特征。而且，该方法本质上是环境友好的，并且适用于多种芳烃/吲哚以及α，β-不饱和酮。