1,3-Dimethyl-5-(4-phenoxy-but-2-ynyloxy)-1H-pyrimidine-2,4-dione | 198219-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-Dimethyl-5-(4-phenoxy-but-2-ynyloxy)-1H-pyrimidine-2,4-dione
• 英文别名: 1,3-Dimethyl-5-(4-phenoxybut-2-ynoxy)pyrimidine-2,4-dione
• CAS: 198219-19-1
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: WAOYPAYMYIOMGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-5-(4-phenoxy-but-2-ynyloxy)-1H-pyrimidine-2,4-dione 在 palladium diacetate 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以100%的产率得到1,3,8-trimethyl-7-phenoxy-6H-pyrano[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Regioselective synthesis of pyrano[3,2-c]pyrimidine derivatives via a palladium-catalyzed unusual [1,3] aryloxy shift and cycloisomerization: first report of a [1,3] shift of an aryloxy group

  摘要：

  Uracil-annulated pyrano heterocycles are regioselectively synthesized in excellent yields (92-100%) via a palladium-catalyzed unusual [1,3] aryloxy shift followed by 6-endo dig cyclization and [1,3] prototropic shift. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.019
• 作为产物：
  描述：

  5-羟基-1,3-二甲基嘧啶-2,4-二酮 、 1-chloro-4-phenoxybut-2-yne 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 以95%的产率得到1,3-Dimethyl-5-(4-phenoxy-but-2-ynyloxy)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Regioselective Synthesis of 6H-Pyrano[3,2-e]Pyrimidine-2,4-Dione

  摘要：

  7-Aryloxymethyl-1,3-dimethyl-6H-pyrano[3,2-e]pyrimidine-2,4-diones(4a-f) were synthesized in 88-92% yields (isolated) by the regioselectively thermal [3s, 3s] sigmatropic rearrangement of 1,3-dimethyl-5-(1 -aryloxybut-2-ynyloxy)pyrimidine-2,4-diones, (3a-f) in refluxing chlorobenzene (purified) for 2-4 h.

  DOI：

  10.1080/00397919708005924

文献信息

• Regioselective Synthesis of 6H-Pyrano[3,2-e]Pyrimidine-2,4-Dione
  作者：Majumdar、Das

  DOI：10.1080/00397919708005924

  日期：1997.11

  7-Aryloxymethyl-1,3-dimethyl-6H-pyrano[3,2-e]pyrimidine-2,4-diones(4a-f) were synthesized in 88-92% yields (isolated) by the regioselectively thermal [3s, 3s] sigmatropic rearrangement of 1,3-dimethyl-5-(1 -aryloxybut-2-ynyloxy)pyrimidine-2,4-diones, (3a-f) in refluxing chlorobenzene (purified) for 2-4 h.
• Studies in Pyrimidine-Annelated Heterocycles¹ by Tandem Cyclization:  Regioselective Synthesis of [6,6]Pyranopyran by Intramolecular [1,6] Michael Addition
  作者：K. C. Majumdar、U. Das

  DOI：10.1021/jo972058a

  日期：1998.12.1
• Regioselective synthesis of pyrano[3,2-c]pyrimidine derivatives via a palladium-catalyzed unusual [1,3] aryloxy shift and cycloisomerization: first report of a [1,3] shift of an aryloxy group
  作者：K.C. Majumdar、B. Sinha、B. Chattopadhyay、K. Ray

  DOI：10.1016/j.tetlet.2008.05.019

  日期：2008.7

  Uracil-annulated pyrano heterocycles are regioselectively synthesized in excellent yields (92-100%) via a palladium-catalyzed unusual [1,3] aryloxy shift followed by 6-endo dig cyclization and [1,3] prototropic shift. (C) 2008 Elsevier Ltd. All rights reserved.