1-(4-anisyl)hexan-3-one | 90831-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-anisyl)hexan-3-one
• 英文别名: 1-(4-methoxyphenyl)-hexan-3-one；1-(4-Methoxy-phenyl)-hexan-3-on；3-Hexanone,1-(4-methoxyphenyl)-；1-(4-methoxyphenyl)hexan-3-one
• CAS: 90831-80-4
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: NGTQBFARPNIGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-p-Methoxyphenylhex-1-en-3-on 在 monoaluminum phosphate 、 silica gel 、 钯 环己烯 作用下， 反应 3.0h， 以94.9%的产率得到1-(4-anisyl)hexan-3-one
  参考文献：
  名称：

  Alba, A.; Aramendia, A.; Borau, V., Canadian Journal of Chemistry, 1984, vol. 62, p. 917 - 921

  摘要：

  DOI：

文献信息

• Gold- and Silver-Catalyzed Reactions of Propargylic Alcohols in the Presence of Protic Additives
  作者：Matthew N. Pennell、Peter G. Turner、Tom D. Sheppard

  DOI：10.1002/chem.201102830

  日期：2012.4.10

  secondary and tertiary propargylic alcohols undergo a Meyer–Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4‐methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined

  在室温下，在金（I）催化剂和少量MeOH或4-甲氧基苯基硼酸的存在下，大范围的伯，仲和叔炔丙醇会进行Meyer-Schuster重排，从而得到烯酮。以该反应为关键步骤，实现了烯酮天然产物异麦角酮和达芬酮的合成。伯炔丙醇的重排可以很容易地在单锅法中结合，向所得的末端烯酮中添加亲核试剂，得到β-芳基，β-烷氧基，β-氨基或β-硫代酮。带有相邻的富电子芳基的炔丙醇也可以通过氧，氮和碳亲核试剂进行银催化的醇取代。
• A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer−Schuster Rearrangement of Propargylic Alcohols at Room Temperature
  作者：Matthew N. Pennell、Matthew G. Unthank、Peter Turner、Tom D. Sheppard

  DOI：10.1021/jo102263t

  日期：2011.3.4

  Meyer−Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1−2 mol % PPh3AuNTf2, in the presence of 0.2 equiv of 4-methoxyphenylboronic acid or 1 equiv of methanol. Good to excellent yields of enones can be obtained from secondary and tertiary alcohols, with high selectivity for the E-alkene in most cases. A one-pot procedure for the conversion of primary

  在室温下，在0.2当量的4-甲氧基苯基硼酸或1当量的甲醇存在下，在1-2摩尔％的PPh 3 AuNTf 2的甲苯中，炔丙醇的迈尔-舒斯特重排容易发生。可以从仲和叔醇获得良好至优异的烯酮收率，在大多数情况下，对E-烯烃的选择性高。还开发了一种通过一锅法将伯炔丙醇转化为β-芳基酮的方法，方法是通过Meyer-Schuster重排，然后Pd催化添加硼酸。
• Reagent Control Enables Selective and Regiodivergent Opening of Unsymmetrical Phenonium Ions
  作者：Shiyan Xu、Hannah M. Holst、Shelby B. McGuire、Nicholas J. Race

  DOI：10.1021/jacs.0c02095

  日期：2020.5.6

  of selective and regiodivergent opening of unsymmetrical phenonium ions with chloride ions. These reactions are enabled by the dual role of SnCl4 and TiCl4 as Lewis acids and chloride nucleophiles. Reagent control dictates addition of chloride at either the substituted internal position (SnCl4) or unsubstituted terminal position (TiCl4) of the phenonium ion. These reactions are highly selective, stereospecific

  我们报告了非对称苯鎓离子与氯离子的选择性和区域发散性开放的第一个例子。这些反应是通过 SnCl4 和 TiCl4 作为路易斯酸和氯化物亲核试剂的双重作用实现的。试剂控制要求在苯鎓离子的取代内部位置 (SnCl4) 或未取代末端位置 (TiCl4) 添加氯化物。这些反应具有高度选择性、立体有择性、操作简单，并且以良好的收率进行。展示了多样化的产品实用性。
• Heck reactions of aryl bromides with alk-1-en-3-ol derivatives catalysed by a tetraphosphine/palladium complex
  作者：Florian Berthiol、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2004.05.117

  日期：2004.7

  cis,cis,cis-1,2,3,4-Tetrikis(diplienylphosphinomethyl)cyclopentane/[PdCl(C3H5)](2) efficiently catalyses the Heck reaction of alk-1-en-3-ol with a variety of aryl bromides. In the presence of hex-1-en-3-ol or oct-1-en-3-ol, the beta-arylated carbonyl compounds were selectively obtained. Linalool and 2-methylbut-3-en-2-ol led to the corresponding 1-arylalk-1-en-3-ol derivatives. Turnover numbers up to 69,000 can be obtained for this reaction. A minor electronic effect of the substituents of the aryl bromide was observed. Similar reaction rates were observed in the presence of activated aryl bromides Such as bromoacetophenone and deactivated aryl bromides such as bromoanisole. (C) 2004 Elsevier Ltd. All rights reserved.
• Friedmann, Journal fur praktische Chemie (Leipzig 1954), 1936, vol. <2> 145, p. 321,335
  作者：Friedmann

  DOI：——

  日期：——