ethyl 5-(4-chlorophenyl)furan-3-carboxylate | 1371636-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-(4-chlorophenyl)furan-3-carboxylate
• CAS: 1371636-92-8
• 化学式: C₁₃H₁₁ClO₃
• 分子量: 250.682
• InChiKey: LEGSYMQIHVETKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙基3-氟 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 sodium carbonate 、 三(邻甲基苯基)磷 、 4,4'-二叔丁基-2,2'-二吡啶 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 ethyl 5-(4-chlorophenyl)furan-3-carboxylate
  参考文献：
  名称：

  A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates

  摘要：

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.

  DOI：

  10.1021/ol301570t

文献信息

• Gold-catalyzed efficient synthesis of 2,4-disubstituted furans from aryloxy-enynes
  作者：Ende Li、Wenjun Yao、Xin Xie、Chengyu Wang、Yushang Shao、Yanzhong Li

  DOI：10.1039/c2ob07173h

  日期：——

  (E)-1-aryloxy-1-en-3-ynes has been prepared by Sonogashira coupling of 2-bromo-3-aryloxypropenoates with terminal alkynes using Pd(PPh3)4 and CuI as the catalysts in Et3N. The resulting enynyl-aryl ethers are found to be highly applicable to the synthesis of 2,4-disubstituted furans with an ester group at C-4 position through an Au/Ag-catalyzed annulation reaction under extremely mild reaction conditions.

  使用Pd（PPh 3）4和CuI作为Et 3的催化剂，通过Sonogashira将2-溴-3-芳氧基丙酸酯与末端炔烃偶联制备了一系列（E）-1-芳氧基-1-en-3-ynes N.发现所得的炔基-芳基醚非常适用于在极温和的反应条件下通过Au / Ag催化的环化反应合成在C-4位具有酯基的2,4-二取代的呋喃。
• A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates
  作者：Daniel W. Robbins、John F. Hartwig

  DOI：10.1021/ol301570t

  日期：2012.8.17

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.