9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.0(2,7)]trideca-2,4,6-triene-11-one | 159211-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.0(2,7)]trideca-2,4,6-triene-11-one
• 英文别名: 9-Methyl-8-oxa-10,12-diazatricyclo[7.3.1.0,2,7]trideca-2,4,6-trien-11-one；9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-one
• CAS: 159211-12-8
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD00841854
• 分子量: 204.228
• InChiKey: WEWAKYHNJXBLCN-UHFFFAOYSA-N

物化性质

• 熔点：
  283-285 °C(Solv: ethanol (64-17-5))
• 沸点：
  432.7±45.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-acetyl-4-(2-hydroxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one 在 盐酸 、 尿素 作用下， 生成 9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.0(2,7)]trideca-2,4,6-triene-11-one
  参考文献：
  名称：

  Condensation of 5-Acetyl-3,4-dihydropyrimidin-2(1H)-ones with Hydrazine

  摘要：

  3,4-Dihydropyrimidines obtained by the Biginelli reaction react with hydrazine to give a mixture of N-[(3,5-dimethyl-1H-pyrazol-4-yl)(R)methyl]ureas and 4-R-3,7a-dimethyl-1,3a,4,5,7,7a-hexahydro-6H-pyrazolo[3,4-d]pyrimidin-6-ones. The latter transform into N-[(3,5-dimethyl-1H-pyrazol-4-yl)(R)methyl]ureas in an acidic medium.

  DOI：

  10.1134/s1070428019110058

文献信息

• Synthesis of New Pyrimidine, Quinazoline and Diazatricyclo Derivatives by Multicomponent Reaction and Evaluation of Their Biological Activity
  作者：Akbar Mobinikhaledi、Naser Foroughifar、Tahere Mosleh、Ahmad Hamta

  DOI：10.1080/10426507.2011.645175

  日期：2012.6

  Abstract A series of new pyrimidine and quinazoline derivatives was synthesized by a Biginelli-like reaction of urea/thiourea, aldehyde, and ketone in the presence of hydrochloric acid as a catalyst. In a similar way, some novel diazatricyclo derivatives were obtained via a Biginelli-like reaction followed by an intramolecular Michael-type addition. The yields of products were reasonable after recrystallization

  摘要 以尿素/硫脲、醛、酮为原料，以盐酸为催化剂，通过类Biginelli反应合成了一系列新的嘧啶和喹唑啉衍生物。以类似的方式，通过类 Biginelli 反应和分子内迈克尔型加成获得了一些新的二氮杂三环衍生物。乙醇重结晶后产物收率合理。所有新合成的化合物均使用 IR 和 NMR（1H 和 13C）光谱和元素分析进行​​表征。研究了这些化合物对金黄色葡萄球菌（RTCC，1885）和大肠杆菌（ATCC，35922）的抗菌活性。补充材料可用于本文。转至出版商的在线版磷、硫、和硅和相关元素查看免费的补充文件。图形概要
• Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step
  作者：Mihaela Matache、Cristian Dobrota、Niculina D. Bogdan、Ioana Dumitru、Lavinia L. Ruta、Codruta C. Paraschivescu、Ileana C. Farcasanu、Ion Baciu、Daniel P. Funeriu

  DOI：10.1016/j.tet.2009.05.088

  日期：2009.8

  A new efficient approach for the synthesis of functionalized dihydro-pyrimido[4,3-d]coumarins is described. Use of benzyl- or tert-butyl acetoacetate and various salicyl aldehydes in typical Biginelli multicomponent reactions provides esters that can be easily deprotected to yield the corresponding hydroxy acids. Annelation of the latter leads to the target dihydro-pyrimido[4,3-d]coumarins. Formation of some unexpected oxo-bridged tetrahydro-pyrimidines is also described. Spectral properties of the synthesized dihydro-pyrimido[4,3-d]coumarins indicate the necessity to revisit some compounds previously reported as products of direct one-pot Biginelli condensation involving 4-hydroxycoumarin as dicarbonyl component. (C) 2009 Elsevier Ltd. All rights reserved.