6-amino-5-(3-butenoylamino)-1,3-dimethyluracil | 99171-67-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-amino-5-(3-butenoylamino)-1,3-dimethyluracil
• 英文别名: but-3-enoic acid 6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamide；1,3-Dimethyl-4-amino-5-<3-butenoyl-amino>-uracil；N-(4-amino-1,3-dimethyl-2,6-dioxopyrimidin-5-yl)but-3-enamide
• CAS: 99171-67-2
• 化学式: C₁₀H₁₄N₄O₃
• 分子量: 238.246
• InChiKey: BXLPWYTZAXHJGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-5-(3-butenoylamino)-1,3-dimethyluracil 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (E)-8-(1-propenyl)theophylline
  参考文献：
  名称：

  New synthetic approach to 8-allyltheophylline

  摘要：

  The synthesis of 8-allyltheophylline (8) from 5,6-diamino-1,3-dimethyluracil (1) and 3-butenoic acid by Traube's method via 6-amino-5-93-butenoylamino)-1,3-dimethyluracil (2) failed because an attempted alkaline cyclization of the intermediate 2 afforded (E)-8-(1-propenyl)-theophylline (3) under rearrangement of the terminal C=C bond. Therefore, the cyclodehydratation of 6-(3-butenylamino)-5-nitroso-1,3-dimethyluracil (7), available from 6-chloro-1,3-dimethyluracil (5) via 6-(3-butenylamino) derivative 6 has to bc used for obtaining the required product 8.

  DOI：

  10.1007/bf00811849
• 作为产物：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 、 乙烯基乙酸 反应 1.0h， 以64%的产率得到6-amino-5-(3-butenoylamino)-1,3-dimethyluracil
  参考文献：
  名称：

  New synthetic approach to 8-allyltheophylline

  摘要：

  The synthesis of 8-allyltheophylline (8) from 5,6-diamino-1,3-dimethyluracil (1) and 3-butenoic acid by Traube's method via 6-amino-5-93-butenoylamino)-1,3-dimethyluracil (2) failed because an attempted alkaline cyclization of the intermediate 2 afforded (E)-8-(1-propenyl)-theophylline (3) under rearrangement of the terminal C=C bond. Therefore, the cyclodehydratation of 6-(3-butenylamino)-5-nitroso-1,3-dimethyluracil (7), available from 6-chloro-1,3-dimethyluracil (5) via 6-(3-butenylamino) derivative 6 has to bc used for obtaining the required product 8.

  DOI：

  10.1007/bf00811849

文献信息

• New synthetic approach to 8-allyltheophylline
  作者：A. Rybár、J. Alföldi、I. Šmondrková

  DOI：10.1007/bf00811849

  日期：1994.5

  The synthesis of 8-allyltheophylline (8) from 5,6-diamino-1,3-dimethyluracil (1) and 3-butenoic acid by Traube's method via 6-amino-5-93-butenoylamino)-1,3-dimethyluracil (2) failed because an attempted alkaline cyclization of the intermediate 2 afforded (E)-8-(1-propenyl)-theophylline (3) under rearrangement of the terminal C=C bond. Therefore, the cyclodehydratation of 6-(3-butenylamino)-5-nitroso-1,3-dimethyluracil (7), available from 6-chloro-1,3-dimethyluracil (5) via 6-(3-butenylamino) derivative 6 has to bc used for obtaining the required product 8.