3-(p-methoxybenzoyl)-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5a>pyrimidine | 137669-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(p-methoxybenzoyl)-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5a>pyrimidine
• 英文别名: (4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyrimidin-3-yl)(4-methoxyphenyl)methanone；3-(4'-methoxybenzoyl)-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrimidine；(4-Methoxy-phenyl)-(4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyrimidin-3-yl)-methanone；(4-methoxyphenyl)-(4,5,6,7-tetrahydrotriazolo[1,5-a]pyrimidin-3-yl)methanone
• CAS: 137669-31-9
• 化学式: C₁₃H₁₄N₄O₂
• 分子量: 258.28
• InChiKey: VCMONHDZGHGMOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one 在 perfluorobutanesulfonyl azide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以99%的产率得到3-(p-methoxybenzoyl)-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5a>pyrimidine
  参考文献：
  名称：

  以氟烷磺酰基叠氮化物为重氮转移试剂轻松，定量合成1,3-二氮杂杂环融合的1,2,3-三唑衍生物

  摘要：

  通过与氟代链烷磺酰基叠氮化物将杂环烯酮缩醛的1，3-偶极环加成，然后在室温下不用任何催化剂消除氟代链烷磺酰基酰胺，可方便地定量制备一系列1,3-二氮杂杂环稠合的1,2,3-三唑。 氟烷磺酰基叠氮化物-乙烯酮缩醛-1,3-偶极环加成-杂环-1,3-二氮杂杂环稠合的1,2,3-三唑

  DOI：

  10.1055/s-0030-1260043

文献信息

• The reaction of benzoyl-substituted heterocyclic ketene aminals with aryl azides
  作者：Zhitang Huang、Meixiang Wang

  DOI：10.1021/jo00027a035

  日期：1992.1

  The reaction between heterocyclic ketene animals, 2-(benzoylmethylene)imidazolidines 3, -hexahydropyrimidines 4, and phenyl azides 5 was investigated. Both the reaction rate and products were strongly dependent on the substituents on 3 or 4 and 5. The reaction rate decreased with the decrease of the electron-withdrawing ability of the Y on the aryl azide 5 with the order NO2 > Cl > H > CH3O, as well as with the decrease of the electron-donating ability of the X on the 3 or 4 following the order CH3O > CH3 > H > Cl. Substituents X and Y affected the course of the reaction. Thus, 3 or 4 reacted with p-nitrophenyl azide 5a to give exclusively highly substituted 1,2,3-triazole derivatives 6aa-da and 7aa-da. The reaction between 3 or 4 and other aryl azides 5b-d afforded respectively fused triazoles 8a-d or 9a-d (6-31%) in addition to triazoles 6ab-bd or 7ab-bd (8-76%). It is concluded that 3 and 4 behave mostly as nucleophiles rather than 1,3-dipolarophiles in reaction with aryl azides 5. Only in the case of unfavorable electronic factors may 3 and 4 act as 1,3-dipolarophiles toward 5.
• An efficient one-pot synthesis of heterocycle-fused 1,2,3-triazole derivatives as anti-cancer agents
  作者：Sheng-Jiao Yan、Yong-Jiang Liu、Yu-Lan Chen、Lin Liu、Jun Lin

  DOI：10.1016/j.bmcl.2010.06.141

  日期：2010.9

  A series of heterocycle-fused 1,2,3-triazoles were easily prepared by the 1,3-dipolar cycloaddition of heterocyclic ketene aminals or N,O-acetals with sodium azide and polyhalo isophthalonitriles in a one-pot reaction at room temperature without a catalyst and evaluated in vitro against a panel of human tumour cell lines. 1,3-Oxazoheterocycle fused 1,2,3-triazoles were more potent against the tumour cell lines Skov-3, HL-60, A431, A549 and HepG-2 than 1,3-diazoheterocycle fused 1,2,3-triazoles. 4-Methoxyphenyl substituted 1,3-oxazoheterocycle fused 1,2,3-triazole 6j was found to be the most potent derivative with IC50 values lower than 1.9 mu g/mL against A431 and K562 human tumour cell lines. (C) 2010 Elsevier Ltd. All rights reserved.