3-benzoyl-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5-a>pyrimidine | 132111-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5-a>pyrimidine
• 英文别名: (4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyrimidin-3-yl)(phenyl)methanone；phenyl(4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyrimidin-3-yl)methanone；3-benzoyl-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrimidine；Phenyl(4,5,6,7-tetrahydrotriazolo[1,5-a]pyrimidin-3-yl)methanone；phenyl(4,5,6,7-tetrahydrotriazolo[1,5-a]pyrimidin-3-yl)methanone
• CAS: 132111-59-2
• 化学式: C₁₂H₁₂N₄O
• 分子量: 228.253
• InChiKey: RDDKKSBUUCNVLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one 在 对甲苯磺酰叠氮 、 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以83%的产率得到3-benzoyl-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5-a>pyrimidine
  参考文献：
  名称：

  烯胺和甲苯磺酰叠氮化物向N-杂环熔融和5-氨基1,2,3-三唑的无金属过渡态

  摘要：

  的多功能5-氨基官能化的1,2,3-三唑，无论是在N杂环稠合的和非环状的氨基官能化形式形式的合成，已经通过的环反应实现宝石二氨基烯胺酮和甲苯磺酰叠氮化物下transition-无金属的条件。

  DOI：

  10.1002/ejoc.202000938

文献信息

• Facile and Quantitative Synthesis of 1,3-Diazaheterocycle-Fused 1,2,3-Triazole Derivatives Using Fluoroalkanesulfonyl Azide as a Diazo Transfer Reagent
  作者：Shizheng Zhu、Jiwei Gu、Wanting Xiong、Zhenhua Zhang

  DOI：10.1055/s-0030-1260043

  日期：2011.6

  3-triazoles were conveniently and quantitatively prepared by 1,3-dipolar cycloaddition of heterocyclic ketene aminals with fluoroalkanesulfonyl azide, followed by elimination of fluoroalkanesulfonyl amide at room temperature without any catalyst. fluoroalkanesulfonyl azide - ketene aminals - 1,3-dipolar cycloaddition - heterocycles - 1,3-diazaheterocycle-fused 1,2,3-triazole

  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
• 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.
• Transition‐Metal‐Free Annulation of Enamines and Tosyl Azide toward N‐Heterocycle Fused and 5‐Amino‐1,2,3‐Triazoles
  作者：Leiling Deng、Yunyun Liu、Yanping Zhu、Jie‐Ping Wan

  DOI：10.1002/ejoc.202000938

  日期：2020.9.14

  The synthesis of versatile 5‐amino functionalized 1,2,3‐triazoles, both in the forms of N‐heterocycle fused and acyclic amino group functionalized forms, have been realized via the annulation reactions of gem‐diamino enaminones and tosyl azide under transition‐metal‐free conditions.

  的多功能5-氨基官能化的1,2,3-三唑，无论是在N杂环稠合的和非环状的氨基官能化形式形式的合成，已经通过的环反应实现宝石二氨基烯胺酮和甲苯磺酰叠氮化物下transition-无金属的条件。