4-hydroxy-5-[2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]-3,6-dihydro-2H-1,3-thiazine-2,6-dione | 932731-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4-hydroxy-5-[2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]-3,6-dihydro-2H-1,3-thiazine-2,6-dione
• CAS: 932731-33-4
• 化学式: C₂₀H₁₇N₃O₄S
• 分子量: 395.439
• InChiKey: ZOOMZKCPTDRUCM-UHFFFAOYSA-N

物化性质

• 熔点：
  223-224 °C(Solv: 1-propanol (71-23-8))
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  103.78
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-[2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]-3,6-dihydro-2H-1,3-thiazine-2,6-dione 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以30%的产率得到1-(2-aminophenyl)-6-[(E)-2-(4-methoxyphenyl)vinyl]uracil
  参考文献：
  名称：

  Azines and azoles: CXXVI. First example of a novel heterocyclic system: Pyrimido[1,6-a][1,5]benzodiazepines

  摘要：

  4-Hydroxy-5-(2-R-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones readily undergo acylation at the N-1 atom of the benzodiazepine system by the action of acetic anhydride. Heating of the acetylated products in boiling dimethylformamide leads to the formation of 75-93% of the corresponding 7-acetyl-6-R-6,7-dihydropyrimido[1,6-a][1,5]benzodiazepine-1,3-diones that are derivatives of hitherto unknown fused heterocyclic system, pyrimido[1,6-a][1,5]benzodiazepine. 4-Hydroxy-5-(2-R-2,3-dihydro-1H1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones are converted into 1-(2-aminophenyl)-6-(2-R-vinyl)uracils on heating in boiling DMF.

  DOI：

  10.1134/s1070363207120146
• 作为产物：
  描述：

  5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione 在 三氟乙酸 作用下， 以 丙醇 、 异丙醇 为溶剂， 生成 4-hydroxy-5-[2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]-3,6-dihydro-2H-1,3-thiazine-2,6-dione
  参考文献：
  名称：

  Azines and azoles: CXXIII. Three-component condensation of 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione with o-phenylenediamine and carbonyl compounds as a convenient synthesis of substituted 1,5-benzodiazepines

  摘要：

  Readily accessible 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione reacted with an equimolar amount of o-phenylenediamine under mild conditions (propan-2-ol, 5 min, reflux) to give the corresponding Schiff base. Reactions of the latter with aldehydes and ketones in propan-l-ol in the presence of a catalytic amount of trifluoroacetic acid or in acetic acid led to the formation of 4-hydroxy-5(2-R-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones.

  DOI：

  10.1134/s1070363206050240

文献信息

• Azines and azoles: CXXVI. First example of a novel heterocyclic system: Pyrimido[1,6-a][1,5]benzodiazepines
  作者：V. N. Yuskovets、B. A. Ivin

  DOI：10.1134/s1070363207120146

  日期：2007.12

  4-Hydroxy-5-(2-R-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones readily undergo acylation at the N-1 atom of the benzodiazepine system by the action of acetic anhydride. Heating of the acetylated products in boiling dimethylformamide leads to the formation of 75-93% of the corresponding 7-acetyl-6-R-6,7-dihydropyrimido[1,6-a][1,5]benzodiazepine-1,3-diones that are derivatives of hitherto unknown fused heterocyclic system, pyrimido[1,6-a][1,5]benzodiazepine. 4-Hydroxy-5-(2-R-2,3-dihydro-1H1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones are converted into 1-(2-aminophenyl)-6-(2-R-vinyl)uracils on heating in boiling DMF.
• Azines and azoles: CXXIII. Three-component condensation of 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione with o-phenylenediamine and carbonyl compounds as a convenient synthesis of substituted 1,5-benzodiazepines
  作者：V. N. Yuskovets、Berzhe Uankpo、B. A. Ivin

  DOI：10.1134/s1070363206050240

  日期：2006.5

  Readily accessible 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione reacted with an equimolar amount of o-phenylenediamine under mild conditions (propan-2-ol, 5 min, reflux) to give the corresponding Schiff base. Reactions of the latter with aldehydes and ketones in propan-l-ol in the presence of a catalytic amount of trifluoroacetic acid or in acetic acid led to the formation of 4-hydroxy-5(2-R-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones.