5-溴甲基-1,3-二苄基-6-甲基尿嘧啶 | 918631-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴甲基-1,3-二苄基-6-甲基尿嘧啶
• 英文名称: 5-bromomethyl-1,3-dibenzyl-6-methyluracil
• 英文别名: 1,3-Dibenzyl-5-(bromomethyl)-6-methyl-pyrimidine-2,4-dione；1,3-dibenzyl-5-(bromomethyl)-6-methylpyrimidine-2,4-dione
• CAS: 918631-02-4
• 化学式: C₂₀H₁₉BrN₂O₂
• 分子量: 399.287
• InChiKey: SIGNUMVZFSLUMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  5-溴甲基-1,3-二苄基-6-甲基尿嘧啶 在 palladium on activated charcoal 三甲基氯硅烷 、 甲酸铵 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 132.0h， 生成 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 、 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 5-溴甲基-1,3-二苄基-6-甲基尿嘧啶
  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