ethyl (+/-)-6-(azidomethyl)-1,2,3,4-tetrahydro-2-oxo-4-phenyl-5-pyrimidinecarboxylate | 125803-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl (+/-)-6-(azidomethyl)-1,2,3,4-tetrahydro-2-oxo-4-phenyl-5-pyrimidinecarboxylate
• 英文别名: ethyl 6-azidomethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；Iwvzxlkjhjrvea-uhfffaoysa-；ethyl 6-(azidomethyl)-2-oxo-4-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 125803-43-2
• 化学式: C₁₄H₁₅N₅O₃
• 分子量: 301.305
• InChiKey: IWVZXLKJHJRVEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (+/-)-6-(azidomethyl)-1,2,3,4-tetrahydro-2-oxo-4-phenyl-5-pyrimidinecarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以80%的产率得到ethyl 6-(aminomethyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A Facile Synthesis of Functionalized 1,2,6,7-Tetrahydroimidazo[1,5-c]pyrimidine-3,5-diones

  摘要：

  A Pd-mediated hydrogenation of ethyl 6-azidomethyl-1,2,3,4-tetrahydro-4-R-2-oxo-5-pyrimidinecarboxylates leads to the corresponding ethyl 6-aminomethyl1,2,3,4-tetrahydro-4-R-2-oxo-5-pyrimidinecarboxylates. The latter react with bis(trichloromethyl)carbonate, yielding the title ethyl 1,2,3,5,6,7-hexahydro-7-R-3,5-dioxoimidazo[1,5-c]pyrimidine-8-carboxylates. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.707738
• 作为产物：
  描述：

  6-(溴甲基)-2-氧代-4-苯基-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 六甲基磷酰三胺 、 sodium azide 作用下， 反应 72.0h， 以72%的产率得到ethyl (+/-)-6-(azidomethyl)-1,2,3,4-tetrahydro-2-oxo-4-phenyl-5-pyrimidinecarboxylate
  参考文献：
  名称：

  Kappe, Oliver C., Liebigs Annalen der Chemie, 1990, # 5, p. 505 - 507

  摘要：

  DOI：

文献信息

• Chromene-dihydropyrimidinone and xanthene-dihydropyrimidinone hybrids: design, synthesis, and antibacterial and antibiofilm activities
  作者：Samuel J. Santos、Fernanda C. P. Rossatto、Natália S. Jardim、Daiana S. Ávila、Rodrigo Ligabue-Braun、Luiz A. M. Fontoura、Karine R. Zimmer、Dennis Russowsky

  DOI：10.1039/d2nj05211c

  日期：——

  A series of eleven chromene-dihydropyrimidinone and eleven xanthene-dihydropyrimidinone hybrid compounds were easily synthesized through a sequential multicomponent reaction followed by copper-catalyzed alkyne–azide cycloaddition reaction. The antibiofilm and antibacterial activities of hybrids were evaluated against Staphylococcus aureus and Pseudomonas aeruginosa and the antibiofilm property was

  一系列 11 种色烯-二氢嘧啶酮和 11 种呫吨-二氢嘧啶酮杂化化合物通过连续的多组分反应，然后是铜催化的炔烃-叠氮化物环加成反应，很容易合成。杂种的抗生物膜和抗菌活性针对金黄色葡萄球菌和铜绿假单胞菌进行了评估，抗生物膜特性呈剂量依赖性。大多数化合物显示出对金黄色葡萄球菌的抗生物膜活性，而不抑制其生长。在体内，蠕虫急性或长期暴露于15a杂种表现出存活率、育雏大小和体长下降以及凋亡尸体数量增加；然而，这些影响仅在测试的最高浓度下观察到。计算机分析表明，该分子在 SOS 通路中有一个新的靶标，用于诱导 DNA 损伤修复。因此，这些杂化物是很有前途的化合物，可以对抗与难以治疗的慢性感染相关的细菌生物膜。
• Kappe, Oliver C., Liebigs Annalen der Chemie, 1990, # 5, p. 505 - 507
  作者：Kappe, Oliver C.

  DOI：——

  日期：——
• KAPPE, C. OLIVER, LIEBIGS ANN. CHEM.,(1990) N, C. 505-507
  作者：KAPPE, C. OLIVER

  DOI：——

  日期：——
• Synthesis of new polyfunctional 5,6,7,8-tetrahydroimidazo-[1,5-c]pyrimidin-5-ones by the aza-Wittig reaction followed by intramolecular cyclization and 1,3-prototropic shift
  作者：P. S. Lebed’、P. O. Kos、V. V. Polovinko、A. A. Tolmachev、M. V. Vovk

  DOI：10.1134/s1070428009060207

  日期：2009.6

  Ethyl 2-oxo-6-[(triphenyl-lambda(5)-phosphanylidene)aminomethyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylates reacted with organic isocyanates according to the aza-Wittig pattern, and the subsequent intramolecular ring closure and 1,3-H shift resulted in the formation of ethyl 3-alkyl(aryl)amino-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-8-carboxylates.
• A Facile Synthesis of Functionalized 1,2,6,7-Tetrahydroimidazo[1,5-c]pyrimidine-3,5-diones
  作者：Pavlo S. Lebed'、Pavlo O. Kos、Andrey Tolmachev、Mykhaylo V. Vovk、Alexander N. Boyko、Alexey Chekotylo

  DOI：10.1080/00397911.2012.707738

  日期：2013.9.2

  A Pd-mediated hydrogenation of ethyl 6-azidomethyl-1,2,3,4-tetrahydro-4-R-2-oxo-5-pyrimidinecarboxylates leads to the corresponding ethyl 6-aminomethyl1,2,3,4-tetrahydro-4-R-2-oxo-5-pyrimidinecarboxylates. The latter react with bis(trichloromethyl)carbonate, yielding the title ethyl 1,2,3,5,6,7-hexahydro-7-R-3,5-dioxoimidazo[1,5-c]pyrimidine-8-carboxylates. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.