3-(2,6-Dichloro-phenyl)-5,7-dimethyl-7,7a-dihydro-3aH-isoxazolo[5,4-d]pyrimidine-4,6-dione | 135073-84-6

• 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: 3-(2,6-Dichloro-phenyl)-5,7-dimethyl-7,7a-dihydro-3aH-isoxazolo[5,4-d]pyrimidine-4,6-dione
• 英文别名: 3-(2,6-dichlorophenyl)-5,7-dimethyl-3a,7a-dihydro-[1,2]oxazolo[5,4-d]pyrimidine-4,6-dione
• CAS: 135073-84-6
• 化学式: C₁₃H₁₁Cl₂N₃O₃
• 分子量: 328.155
• InChiKey: HGDWNLZTSJKJOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2,6-Dichloro-phenyl)-5,7-dimethyl-7,7a-dihydro-3aH-isoxazolo[5,4-d]pyrimidine-4,6-dione 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 34.0h， 生成 N-(2,6-Dichlorophenyl)-1,3-dimethyl-5-uracilcarboxamide
  参考文献：
  名称：

  Reactivity of nitrile oxides toward the 5,6-double bond of uracil derivatives: synthesis of some 5-aroylpyrimidine nucleoside oximes

  摘要：

  The 5-aroylpyrimidine nucleoside oximes 3-10 were prepared in moderate to good yield by the reaction of the corresponding pyrimidine nucleosides 2a-d with stable nitrile oxides. The nitrile oxides were generated in situ from the corresponding hydroximoyl chlorides 1a-e. From these reactions, only the 1,3-addition products 3-10 were obtained. No products of cycloaddition could be isolated. The 1,3-addition products 3-10 could be formed from the ring-opening reaction of the initially formed 1,3-cycloaddition products. Evidence that supports the proposed mechanism came from experiments that used 1,3-dimethyluracil (13) as the substrate.

  DOI：

  10.1021/jo00030a011
• 作为产物：
  描述：

  2,6-dichlorobenzohydroximoyl chloride 、 1,3-二甲基脲嘧啶 以 甲苯 为溶剂， 反应 72.0h， 以48%的产率得到3-(2,6-Dichloro-phenyl)-5,7-dimethyl-7,7a-dihydro-3aH-isoxazolo[5,4-d]pyrimidine-4,6-dione
  参考文献：
  名称：

  Reactivity of nitrile oxides toward the 5,6-double bond of uracil derivatives: synthesis of some 5-aroylpyrimidine nucleoside oximes

  摘要：

  The 5-aroylpyrimidine nucleoside oximes 3-10 were prepared in moderate to good yield by the reaction of the corresponding pyrimidine nucleosides 2a-d with stable nitrile oxides. The nitrile oxides were generated in situ from the corresponding hydroximoyl chlorides 1a-e. From these reactions, only the 1,3-addition products 3-10 were obtained. No products of cycloaddition could be isolated. The 1,3-addition products 3-10 could be formed from the ring-opening reaction of the initially formed 1,3-cycloaddition products. Evidence that supports the proposed mechanism came from experiments that used 1,3-dimethyluracil (13) as the substrate.

  DOI：

  10.1021/jo00030a011

文献信息

• A Study on the Ring Transformation of Dihydroisoxazolopyrimidine
  作者：Jae Nyoung Kim、Hong Jung Lee、Hyoung Rae Kim、Eung K. Ryu

  DOI：10.1080/00397919708005650

  日期：1997.10

  Dihydroisoxazolopyrimidine derivatives could be cleaved to form either pyrimidine ring or isoxazole ring derivatives depending upon the reaction conditions employed.