methyl 5-cyano-4,6-diphenyl-2H-pyran-3-carboxylate | 1253802-06-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 5-cyano-4,6-diphenyl-2H-pyran-3-carboxylate
• CAS: 1253802-06-0
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: LGWKFJJDBSIMOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-benzoyl-3-phenylacrylonitrile 、 丙炔酸甲酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以96%的产率得到methyl 5-cyano-4,6-diphenyl-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application

  摘要：

  A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20 mol %), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.043

文献信息

• Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application
  作者：Qiongmei Zhang、Tong Fang、Xiaofeng Tong

  DOI：10.1016/j.tet.2010.07.043

  日期：2010.10

  A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20 mol %), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect. (C) 2010 Elsevier Ltd. All rights reserved.