2-hydroxy-8-methyl-3-(2-methylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one | 252950-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-hydroxy-8-methyl-3-(2-methylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one
• 英文别名: 2-hydroxy-8-methyl-3-(2-methyl-1-propenyl)-4H-pyrido[1,2-a]pyrimidin-4-one；4H-Pyrido[1,2-a]pyrimidin-4-one, 2-hydroxy-8-methyl-3-(2-methyl-2-propenyl)-；2-hydroxy-8-methyl-3-(2-methylprop-1-enyl)pyrido[1,2-a]pyrimidin-4-one
• CAS: 252950-65-5
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: HCHXFGMRUQMNIS-UHFFFAOYSA-N

物化性质

• 沸点：
  381.2±52.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-8-methyl-3-(2-methylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one 在 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以100%的产率得到2,2,8-trimethyl-2,3-dihydro-4H-furo[2,3-d]pyrido[1,2-a]-pyrimidin-4-one
  参考文献：
  名称：

  3- alkenylpyrido [1,2的环化一个]嘧啶向呋喃并[2,3- d ]吡啶并[1,2一]嘧啶

  摘要：

  3-烯基吡啶并[1,2 - a ]嘧啶在温和的条件下反应，以高收率得到新颖的三环呋喃并[2,3- d ]吡啶并[1,2- a ]嘧啶。环化反应在酸催化剂的存在下进行。产品收率受所用酸的类型和强度影响。当使用有机酸如三氟甲磺酸和三氟乙酸时，获得了异常高的收率。另一方面，硫酸提供了所检查的无机酸的最佳结果。

  DOI：

  10.1016/s0040-4039(03)00087-x
• 作为产物：
  描述：

  2-氨基-4-甲基吡啶 、 亚异丁基丙二酸二乙酯 以 乙醇 为溶剂， 以91%的产率得到2-hydroxy-8-methyl-3-(2-methylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one
  参考文献：
  名称：

  Electro-organic Reactions. Part 49. The Synthesis and Stereoselective Electrochemical Hydroxylation of 2,3-Dihydro-4H-furo[2,3-d]pyrido[1,2-a]pyrimidin-4-ones.

  摘要：

  Attempted electrochemical (anodic) hydroxylation of pyridopyrimidine derivatives in the pyridine ring, using trifluoroacetate as nucleophile, fails because enol forms predominate which undergo anodic C-O coupling. Substitution, aimed at precluding enolisation, led to an alternative tautomerisation to 8-methyl-3-alkylmethylene-4H-pyrido [1,2-a]pyrimidine-2,4-diones which in acidic solution are converted into the title compounds. The 8-methyl-2,3-dihydro-4H-furo[2,3-d]pyrido[1,2-a]pyrimidine-4-ones are novel and have been fully characterised by spectroscopy and X-ray crystallography. They are electroactive and are oxidised anodically in trifluoroacetic acid-dichloromethane-triethylammonium trifluoroacetate solutions to give the corresponding 3-hydroxy derivatives in good yield. Several examples of this allylic substitution reaction are presented; for cases disubstituted at the 2-position (R-1,R-2) diastereoselective hydroxylation with d.e. ca. 50% (3:1) is observed in which preferential nucleophilic attack on the stabilised intermediate allylic cation occurs at the least hindered face. The stereochemistry of the 3-hydroxy derivatives was assigned by NOE experiments.

  DOI：

  10.3891/acta.chem.scand.53-0901