ethyl 2,4-diphenylfuran-3-carboxylate

• 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 2,4-diphenylfuran-3-carboxylate
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: UBTQPBNCIOMNNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  苯基乙炔基三甲基硅烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 ethyl 2,4-diphenylfuran-3-carboxylate
  参考文献：
  名称：

  Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides:  First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate

  摘要：

  The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)] selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and Se-77 high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.

  DOI：

  10.1021/jo980999x

文献信息

• Highly efficient synthesis of 2,3,4-trisubstituted furans via silver-catalyzed sequential nucleophilic addition and cyclization reactions of haloalkynes
  作者：Wei Zeng、Wanqing Wu、Huanfeng Jiang、Yadong Sun、Zhengwang Chen

  DOI：10.1016/j.tetlet.2013.05.140

  日期：2013.8

  regioselective synthesis of 2,3,4-trisubstituted furans using AgNO3 catalyst from haloalkynes in a one-pot procedure has been reported. The transformation consists of a sequential silver-catalyzed nucleophilic addition and cyclization reaction of haloalkynes. A wide variety of haloalkynes can be used in this chemical process.

  已经报道了使用一锅法从卤代炔烃中使用AgNO 3催化剂进行区域选择性合成2,3,4-三取代的呋喃。该转化由卤代炔烃的连续银催化亲核加成和环化反应组成。在该化学过程中可以使用各种各样的卤代炔烃。
• Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides:  First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate
  作者：Tadashi Kataoka、Shin-ichi Watanabe、Keiichirou Yamamoto、Mitsuhiro Yoshimatsu、Genzoh Tanabe、Osamu Muraoka

  DOI：10.1021/jo980999x

  日期：1998.9.1

  The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)] selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and Se-77 high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.