2-hydroxy-8-methyl-3-(2-phenylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one | 252950-62-2

• 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-phenylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one
• 英文别名: 2-hydroxy-8-methyl-3-(2-phenyl-1-propenyl)-4H-pyrido[1,2-a]pyrimidin-4-one；2-Hydroxy-8-methyl-3-(2-phenylprop-1-enyl)pyrido[1,2-a]pyrimidin-4-one；2-hydroxy-8-methyl-3-(2-phenylprop-1-enyl)pyrido[1,2-a]pyrimidin-4-one
• CAS: 252950-62-2
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: JHNUEIYEFPNZPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-phenylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one 在 硫酸 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以96%的产率得到(+/-)-2,8-methyl-2-phenyl-2,3-dihydro-4-H-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 、 diethyl 2-phenylpropylidenemalonate 以 乙醇 为溶剂， 以65%的产率得到2-hydroxy-8-methyl-3-(2-phenylprop-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

文献信息

• 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.
  作者：James H. P. Utley、Mikhail Elinson、Mustafa Güllü、Ralf Ludwig、Majid Motevalli、Hiroaki Murase、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0901

  日期：——

  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.
• Cyclisation of 3-alkenylpyrido[1,2-a]pyrimidines to furo[2,3-d]pyrido[1,2-a]pyrimidines
  作者：Mustafa Güllü、Sibel Uzun、Serkan Yalçιn

  DOI：10.1016/s0040-4039(03)00087-x

  日期：2003.2

  3-Alkenylpyrido[1,2-a]pyrimidines react under mild conditions to give novel tricyclic furo[2,3-d]pyrido[1,2-a]pyrimidines in high yields. The cyclisation takes place in the presence of an acid catalyst. The product yield is affected by the type and the strength of the acid used. Exceptionally high yields were obtained when an organic acid like trifluoromethanesulfonic acid and trifluoroacetic acid

  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。