methyl 2-([1,1'-biphenyl]-4-yl)-2-phenylacetate | 94866-57-6

• 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-([1,1'-biphenyl]-4-yl)-2-phenylacetate
• 英文别名: Methyl 2-phenyl-2-(4-phenylphenyl)acetate；methyl 2-phenyl-2-(4-phenylphenyl)acetate
• CAS: 94866-57-6
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: OYWCTNGPRUKFPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  methyl 2-(4-hydroxyphenyl)-2-phenylacetate 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 methyl 2-([1,1'-biphenyl]-4-yl)-2-phenylacetate
  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

文献信息

• Iron-catalyzed arylation of α-aryl-α-diazoesters
  作者：Ji-Min Yang、Yan Cai、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1039/c5ob02418h

  日期：——

  An iron-catalyzed arylation of α-aryl-α-diazoesters with electron-rich benzene rings was developed, which provides an efficient method for the preparation of 1,1-diarylacetates with high yields and excellent chemo- and regio-selectivities.

  开发了铁催化的α-芳基-α-重氮酸酯与富电子苯环的芳基化反应，这为高产率，优异的化学选择性和区域选择性提供了一种制备1,1-二芳基乙酸酯的有效方法。
• Rhodium Catalyzed Arylation of Diazo Compounds with Aryl Boronic Acids
  作者：Jayanta Ghorai、Pazhamalai Anbarasan

  DOI：10.1021/jo502922r

  日期：2015.4.3

  general and efficient synthesis of diarylacetate, a diarylmethine derivative, was accomplished through rhodium catalyzed direct arylation of diazo compounds with arylboronic acids. The reaction tolerates various boronic acid derivatives and functional groups. Notably, chemoselective arylation of diazo compounds over other electrophiles were demonstrated. The efficacy of the developed methodology is shown

  通过铑催化的重氮化合物与芳基硼酸的直接芳基化反应，可以实现二芳基次甲基衍生物二芳基乙酸酯的一般有效合成。该反应可耐受各种硼酸衍生物和官能团。值得注意的是，证明了重氮化合物相对于其他亲电试剂的化学选择性芳基化。快速合成双氯芬素的核心结构表明了所开发方法的有效性。
• Rh(I)-Catalyzed Cross-Coupling of α-Diazoesters with Arylsiloxanes
  作者：Ying Xia、Zhen Liu、Sheng Feng、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1021/acs.orglett.5b00052

  日期：2015.2.20

  An Rh(I)-catalyzed cross-coupling of diazoesters with arylsiloxanes has been successfully achieved. This transformation is a new method for the construction of the C(sp(3))C(sp(2)) bond, thus providing an alternative synthesis of a-aryl esters. Rh(I)carbene migratory insertion has been proposed to be involved in this coupling reaction. The reaction represents the first example of utilizing arylsiloxane as the coupling partner in the carbene-involved cross-coupling reactions.
• Highly Site-Selective Direct C–H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis
  作者：Zhunzhun Yu、Ben Ma、Mingjin Chen、Hai-Hong Wu、Lu Liu、Junliang Zhang

  DOI：10.1021/ja503163k

  日期：2014.5.14

  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.