diethyl (4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-yl)phosphonate | 1293917-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: diethyl (4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-yl)phosphonate
• 英文别名: 2-[diethoxy(oxido)phosphaniumyl]-2-phenyl-3H-pyran-4-one
• CAS: 1293917-89-1
• 化学式: C₁₅H₁₉O₅P
• 分子量: 310.287
• InChiKey: PKXWXFUFFYSKFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲酰膦酸二乙酯 、 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以89%的产率得到diethyl (4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-yl)phosphonate
  参考文献：
  名称：

  Hetero Diels–Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates

  摘要：

  We have prepared glycosyl type phosphonates via hetero Diels-Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky's diene required thermal activation to yield the desired dihydropyranones in good yield (70-91%). The reactions with Brassard's diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33-69%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.007

文献信息

• Hetero Diels–Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates
  作者：Sidika Polat-Cakir、Ayhan S. Demir

  DOI：10.1016/j.tet.2011.02.007

  日期：2011.4

  We have prepared glycosyl type phosphonates via hetero Diels-Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky's diene required thermal activation to yield the desired dihydropyranones in good yield (70-91%). The reactions with Brassard's diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33-69%). (C) 2011 Elsevier Ltd. All rights reserved.