lin-Benzo-1,9-methylxanthine | 93355-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: lin-Benzo-1,9-methylxanthine
• 英文别名: 3,7-Dimethyl-3H-imidazo[4,5-g]quinazoline-6,8(5H,7H)-dione；3,7-dimethyl-5H-imidazo[4,5-g]quinazoline-6,8-dione
• CAS: 93355-95-4
• 化学式: C₁₁H₁₀N₄O₂
• 分子量: 230.226
• InChiKey: XSCPFVNJHGNVJV-UHFFFAOYSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲酸 、 3-methyl-7-(N-methylamino)-6-nitroquinazoline-2,4(1H,3H)-dione 在 palladium on activated charcoal 氢气 作用下， 以92%的产率得到lin-Benzo-1,9-methylxanthine
  参考文献：
  名称：

  The synthesis oflin-benzoreumycin,lin-benzo-1-methylxanthine, andlin-benzo-1,9-dimethylxanthine

  摘要：

  AbstractCommencing with 7‐chloro‐3‐methylquinazoline‐2,4(1H,3H)‐dione (9a), a five step synthesis of 7‐methylpyrimido[5,4‐g]‐1,2,4‐benzotriazine‐6,8(7H,9H)‐dione (lin‐benzoreumycin, 6) has been accomplished. A synthesis of 1,7‐dimethylpyrimido[5,4‐g]‐1,2,4‐benzotriazine‐6,8(1H,7H)‐dione (lin‐benzotoxoflavin, 5) employing an intermediate from the preparation of 6 (i.e., 7‐chloro‐3‐methyl‐6‐nitroquinazoline‐2,4(1H,3H)‐dione, 9b) was attempted but could not be accomplished beyond the dihydro precursor of 5 (i.e., 12). Compound 9b did lead to successful preparations of 7‐methylimidazo[4,5‐g]quinazoline‐6,8(5H,7H)‐dione (lin‐benzo‐1‐methylxanthine, 7) and 3,7‐dimethylimidazo[4,5‐g]quinazoline‐6,8(5H,7H)‐dione (lin‐benzo‐1,9‐dimethylxanthine, 8) by first reacting 9b with ammonia (for 7) or methylamine (for 8) followed by reductive cyclization in formic acid.

  DOI：

  10.1002/jhet.5570210331

文献信息

• The synthesis of<i>lin</i>-benzoreumycin,<i>lin</i>-benzo-1-methylxanthine, and<i>lin</i>-benzo-1,9-dimethylxanthine
  作者：Stewart W. Schneller、Augusto C. Ibay、William J. Christ

  DOI：10.1002/jhet.5570210331

  日期：1984.5

  AbstractCommencing with 7‐chloro‐3‐methylquinazoline‐2,4(1H,3H)‐dione (9a), a five step synthesis of 7‐methylpyrimido[5,4‐g]‐1,2,4‐benzotriazine‐6,8(7H,9H)‐dione (lin‐benzoreumycin, 6) has been accomplished. A synthesis of 1,7‐dimethylpyrimido[5,4‐g]‐1,2,4‐benzotriazine‐6,8(1H,7H)‐dione (lin‐benzotoxoflavin, 5) employing an intermediate from the preparation of 6 (i.e., 7‐chloro‐3‐methyl‐6‐nitroquinazoline‐2,4(1H,3H)‐dione, 9b) was attempted but could not be accomplished beyond the dihydro precursor of 5 (i.e., 12). Compound 9b did lead to successful preparations of 7‐methylimidazo[4,5‐g]quinazoline‐6,8(5H,7H)‐dione (lin‐benzo‐1‐methylxanthine, 7) and 3,7‐dimethylimidazo[4,5‐g]quinazoline‐6,8(5H,7H)‐dione (lin‐benzo‐1,9‐dimethylxanthine, 8) by first reacting 9b with ammonia (for 7) or methylamine (for 8) followed by reductive cyclization in formic acid.