Methyl 2-hydroxy-2-(2-methoxyphenyl)-2-phenylacetate | 1373334-78-1

• 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: Methyl 2-hydroxy-2-(2-methoxyphenyl)-2-phenylacetate
• CAS: 1373334-78-1
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: XLIXNPWBQGMUOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-hydroxy-2-(2-methoxyphenyl)-2-phenylacetate 在 高氯酸 、 potassium carbonate 作用下， 以 溴苯 、 硝基甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 5-bromo-3-(2-methoxyphenyl)-3-phenyl-7H-furo[2,3-f]chromen-2-one
  参考文献：
  名称：

  Metal-Free Tandem Friedel–Crafts/Lactonization Reaction to Benzofuranones Bearing a Quaternary Center at C3 Position

  摘要：

  A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO4 was reported. A variety of tertiary alpha-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. H-1 NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.

  DOI：

  10.1021/jo300395x

文献信息

• A Highly Efficient Friedel–Crafts Reaction of Tertiary α‐Hydroxyesters or α‐Hydroxyketones to α‐Quaternary Esters or Ketones
  作者：Long Chen、Jian Zhou

  DOI：10.1002/asia.201200693

  日期：2012.11

  A catalytic Friedel–Crafts arylation of α‐hydroxyesters or α‐hydroxyketones with electron‐rich aromatic compounds to furnish α‐quaternary esters/ketones has been developed. The cheap and easy to handle catalyst HClO4 (70 %, aq) was identified as a powerful catalyst for this arylation reaction.

  已经开发了α-羟基酯或α-羟基酮与富电子芳族化合物的催化弗里德-克拉夫特芳基化反应，以提供α-季酯/酮。廉价且易于处理的催化剂HClO 4（70％，aq）被确定为该芳基化反应的有力催化剂。
• Metal-Free Azidation of α-Hydroxy Esters and α-Hydroxy Ketones Using Azidotrimethylsilane
  作者：Xiao-Ping Yin、Lei Zhu、Jian Zhou

  DOI：10.1002/adsc.201701345

  日期：2018.3.20

  We herein report a commercially available perchloric acid catalyst capable of catalyzing the azidation of α‐hydroxy esters, α‐hydroxy ketones and taddols using azidotrimethylsilane in dichloromethane at room temperature. Various substituted tertiary alcohols are well tolerated in this reaction. Cα‐tetrasubstituted α‐amino acid derivatives were prepared by one‐pot sequential azidation and hydrogenation

  我们在此报告了一种可商购的高氯酸催化剂，它能够在室温下在二氯甲烷中使用叠氮三甲基硅烷催化α-羟基酯，α-羟基酮和他达醇的叠氮化。在该反应中，各种取代的叔醇具有良好的耐受性。Ç α -tetrasubstitutedα氨基酸衍生物通过一锅顺序叠氮化和氢化方法制备。这种新开发的方法的优势包括操作简便，催化剂容易获得，规模放大能力以及良好的官能团兼容性。