8-bromo-2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3,5-benzoxadiazocin-4-one | 896704-20-4

• 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: 8-bromo-2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3,5-benzoxadiazocin-4-one
• 英文别名: 4-bromo-9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-11-one
• CAS: 896704-20-4
• 化学式: C₁₁H₁₁BrN₂O₂
• mdl: MFCD03450299
• 分子量: 283.125
• InChiKey: XHQRTYLILGVIHU-UHFFFAOYSA-N

物化性质

• 熔点：
  293-296 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  467.7±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：

  6-methyl-4-(5-bromo-2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以78%的产率得到8-bromo-2-methyl-2,3,5,6-tetrahydro-4H-2,6-methano-1,3,5-benzoxadiazocin-4-one
  参考文献：
  名称：

  Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.05.088

文献信息

• 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.