1,3,5-tetrabenzyl-6-methyluracil | 918631-04-6

• 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: 1,3,5-tetrabenzyl-6-methyluracil
• 英文别名: 1,3,5-tribenzyl-6-methylpyrimidine-2,4(1H,3H)-dione；1,3,5-Tribenzyl-6-methyl-pyrimidine-2,4-dione；1,3,5-tribenzyl-6-methylpyrimidine-2,4-dione
• CAS: 918631-04-6
• 化学式: C₂₆H₂₄N₂O₂
• 分子量: 396.489
• InChiKey: PJTKSHMQZVWOSO-UHFFFAOYSA-N

物化性质

• 沸点：
  566.8±60.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,5-tetrabenzyl-6-methyluracil 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以60%的产率得到5-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors

  摘要：

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.

  DOI：

  10.1080/00397910600772850
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 盐酸 、 barium dihydroxide 、 三甲基氯硅烷 、 氢溴酸 、 sodium hydride 、 溶剂黄146 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 1,3,5-tetrabenzyl-6-methyluracil
  参考文献：
  名称：

  Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors

  摘要：

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.

  DOI：

  10.1080/00397910600772850

文献信息

• 一种制备尿嘧啶和胸腺嘧啶衍生物的方法
  申请人：武汉大学

  公开号：CN111909100B

  公开（公告）日：2022-03-04

  本发明提供了一种高效多样化合成尿嘧啶和胸腺嘧啶衍生物的方法。该方法先将碘代尿嘧啶和胸腺嘧啶类化合物、亲电试剂(卤代烷烃或者溴代芳烃类化合物)、亲核试剂(烯烃、炔烃、硼酸酯等)、钯催化剂、降冰片烯衍生物、碱(碳酸钾)一起溶于有机溶剂(1,4‑二氧六环或者乙二醇二甲醚)中，然后在50～150℃下搅拌反应，反应后分离提纯，即可高效经济、绿色地合成多取代的尿嘧啶和胸腺嘧啶类化合物。该方法条件温和，底物普适性好，产率高，所制备的2‑吡啶酮类与尿嘧啶类化合物广泛地应用在药物化学和有机化学领域。除此以外，还提供了一类抗HIV药物的关键中间体的合成方法，提高了步骤经济性。
• Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors
  作者：Yanli Chen、Ying Guo、Hua Yang、Xiaowei Wang、Junyi Liu

  DOI：10.1080/00397910600772850

  日期：2006.9.1

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.