methyl 2-[(1E,3Z)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-prop-1-enyl]-3-methoxybenzoate | 1070363-61-9

• 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 2-[(1E,3Z)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-prop-1-enyl]-3-methoxybenzoate
• 英文别名: methyl 3-methoxy-2-[(1E,3Z)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-1-propenyl]benzoate；methyl 2-[(E,3Z)-3-(5-fluoro-1,3-dimethyl-2-oxopyrimidin-4-ylidene)prop-1-enyl]-3-methoxybenzoate
• CAS: 1070363-61-9
• 化学式: C₁₈H₁₉FN₂O₄
• 分子量: 346.358
• InChiKey: JDTPIDSKDWUCEM-GHXLPOHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,5-二甲氧基萘 、 1,3-二甲基-5-氟尿嘧啶 以 苯 为溶剂， 以64%的产率得到methyl 2-[(1E,3E)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-prop-1-enyl]-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis of Highly Conjugated Arylpropenylidene-1,3-diazin-2-ones via Paterno–Büchi Reaction by Photoreaction of 5-Fluoro-1,3-dimethyluracil with 1-Methoxynaphthalenes

  摘要：

  与5-氟-1,3-二甲基尿嘧啶（5-FDMU）与各种萘类化合物（包括2-甲氧基萘）发生反应，形成通过1,4-环加成反应生成的乙烯基喹唑啉相对，5-FDMU与在C-1位有甲氧基的萘类化合物混合物的紫外线辐照反应产生了新型环加合物，甲基2-[(1E)-3-(5-氟-1,3-二甲基-2-氧基-1,3-二氢嘧啶-4-亚基)丙-1-烯基]苯甲酸酯，这些化合物源自新型芳香Paterno–Büchi型环加成反应，随后伴随最初形成的氧杂环部分的破坏。

  DOI：

  10.1246/cl.2008.872

文献信息

• Synthesis of Highly Conjugated Arylpropenylidene-1,3-diazin-2-ones via Paterno–Büchi Reaction by Photoreaction of 5-Fluoro-1,3-dimethyluracil with 1-Methoxynaphthalenes
  作者：Koh-ichi Seki、Kazuya Aizawa、Tatsuyuki Sugaoi、Masayuki Kimura、Kazue Ohkura

  DOI：10.1246/cl.2008.872

  日期：2008.8.5

  In contrast to photoreactions of 5-fluoro-1,3-dimethyluracil (5-FDMU) with various naphthalenes including 2-methoxynaphthalenes that proceeds in a manner to give ethenoquinazolines through 1,4-cycloaddition, UV-irradiation of a mixture of 5-FDMU and naphthalenes with a methoxy group at C-1 gave rise to the formation of novel cycloadducts, methyl 2-[(1E)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)prop-1-enyl]benzoates, derived from the novel aromatic Paterno–Büchi type cycloaddition, followed by a concomitant disruption of the initially formed oxetane moiety.

  与5-氟-1,3-二甲基尿嘧啶（5-FDMU）与各种萘类化合物（包括2-甲氧基萘）发生反应，形成通过1,4-环加成反应生成的乙烯基喹唑啉相对，5-FDMU与在C-1位有甲氧基的萘类化合物混合物的紫外线辐照反应产生了新型环加合物，甲基2-[(1E)-3-(5-氟-1,3-二甲基-2-氧基-1,3-二氢嘧啶-4-亚基)丙-1-烯基]苯甲酸酯，这些化合物源自新型芳香Paterno–Büchi型环加成反应，随后伴随最初形成的氧杂环部分的破坏。
• New Results on the Photoreactivity of 5-Fluoro-1,3-dimethyluracil with Methoxylated Naphthalenes
  作者：Kazue Ohkura、Koh-ichi Seki、Kazuya Aizawa、Rie Mukaida、Hiromichi Akizawa

  DOI：10.3987/com-12-s(n)116

  日期：——

  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.