methyl 4-methoxy-2-[(1E,3E)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-1-propenyl]benzoate | 1449306-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-methoxy-2-[(1E,3E)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-1-propenyl]benzoate
• CAS: 1449306-16-4
• 化学式: C₁₈H₁₉FN₂O₄
• 分子量: 346.358
• InChiKey: RQIHIDQVIBGWKC-OWRQJNCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基萘 、 1,3-二甲基-5-氟尿嘧啶 以 环己烷 为溶剂， 反应 10.0h， 以39%的产率得到methyl 4-methoxy-2-[(1E,3E)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-1-propenyl]benzoate
  参考文献：
  名称：

  New Results on the Photoreactivity of 5-Fluoro-1,3-dimethyluracil with Methoxylated Naphthalenes

  摘要：

  Photocycloaddition of 5-fluoro-1,3-dimethyluracil (5-FDMU) with various methoxy and dimethoxynaphthalenes was investigated. Reaction of 5-FDMU with 1,x-dimethoxynaphthalenes (x = 4-7) gave rise to the selective formation of cycloadducts, conjugated arylpropenylidene-1,3-diazin-2-ones, which were derived from an initially formed oxetane moiety via the Paterno-Buchi reaction cycloadduct. The present study shows that the presence of a methoxy substituent on the alpha-position in naphthalene is essential for the formation of products through the Paterno-Buchi reaction. This unique photoreaction involving formation of an oxetane between 5-FDMU and a naphthalene ring, followed by a concomitant disruption of the initially formed oxetane moiety and an aromatic ring of naphthalene moiety, can be regarded as a novel aromatic Paterno-Buchi reaction.

  DOI：

  10.3987/com-12-s(n)116