methyl 2-(4-hydroxyphenyl)-2-(naphthalen-2-yl)acetate | 1609003-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-(4-hydroxyphenyl)-2-(naphthalen-2-yl)acetate
• CAS: 1609003-62-4
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: SYIQZBBRECSLDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  methyl (naphth-2-yl)diazoacetate 、 苯酚 在 silver hexafluoroantimonate 、 [tris(2,4-di-tert-butylphenyl)phosphine]gold chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以66%的产率得到methyl 2-(4-hydroxyphenyl)-2-(naphthalen-2-yl)acetate
  参考文献：
  名称：

  Highly Site-Selective Direct C–H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis

  摘要：

  An unprecedented direct C H bond functionalization of unprotected phenols with alpha-aryl alpha-diazoacetates and diazooxindoles was developed. A tris(2,4-di-tert-butylphenyl) phosphite derived gold complex promoted the highly chemoselective and site-selective C H bond functionalization of phenols and N-acylanilines with gold-carbene generated from the decomposition of diazo compounds, furnishing the corresponding products in moderate to excellent yields at rt. The salient features of this reaction include readily available starting materials, unprecedented C H functionalization rather than X H insertion, good substrate scope, mild conditions, high efficiency, and ease in further transformation. To the best of our knowledge, this is the first example of C H functionalization of unprotected phenols with diazo compounds.

  DOI：

  10.1021/ja503163k