ethyl 2-(3,4-dihydro-3-oxo-6-cyano-2H-1,4-benzoxazin-4-yl)acetate | 221225-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(3,4-dihydro-3-oxo-6-cyano-2H-1,4-benzoxazin-4-yl)acetate
• 英文别名: Ethyl 2-(6-cyano-3-oxo-1,4-benzoxazin-4-yl)acetate
• CAS: 221225-72-5
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: WZIYITRNXUVQIV-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  516.8±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3,4-dihydro-3-oxo-6-cyano-2H-1,4-benzoxazin-4-yl)acetate 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.3h， 生成 2-[6-(4,5-dihydro-1,3-thiazol-2-yl)-3-oxo-1,4-benzoxazin-4-yl]-N-methylacetamide
  参考文献：
  名称：

  Synthesis by microwave irradiation of a substituted benzoxazine parallel library with preferential relaxant activity for guinea pig trachealis

  摘要：

  An efficient, facile, and practical parallel combinatorial synthesis of substituted-benzoxazines under microwave irradiation was described. The procedure involved the use of a microwave oven especially designed for organic synthesis suitable for parallel synthesis of solution libraries. A demonstration 19-membered library of substituted N,N-dimethyl- and N-methyl-benzoxazine amide derivatives, structurally related to the potassium channel opener cromakalim, was generated by both conventional and microwave procedures, achieving a reduction from 7 h to 30-36 min in library generation time for the microwave approach. All the synthesized compounds were tested using the in vitro models of rat aorta and guinea pig trachea rings pre-contracted with phenylephrine and carbachol, respectively. All N,N-dimethyl amide derivatives showed a relaxant activity higher on guinea pig trachea rings than on rat aorta rings. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.05.003
• 作为产物：
  描述：

  2-氨基-4-氰基苯酚 在 sodium hydride 、 sodium carbonate 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 ethyl 2-(3,4-dihydro-3-oxo-6-cyano-2H-1,4-benzoxazin-4-yl)acetate
  参考文献：
  名称：

  Synthesis, biological activity and conformational study of 1,4-benzoxazine derivatives as potassium channel modulators

  摘要：

  With the aim of discovering new molecules with K+-channel activating properties, we have synthesized derivatives of cromakalim (CRK), an important molecule which shows specific affinity towards K+ channels, by replacing the benzopyrane ring of this reference compound with a 1,4-benzoxazine moiety. A different number of substituents showing a good discrimination between hydrophobic and electronic properties have been inserted at the 6-position of the 1,4-benzoxazine ring. We describe here the synthesis and discuss the solid state conformation of these new molecules. When tested on rat aorta ring precontracted with phenylephrine, two compounds (2c and 2d) showed a concentration-dependent relaxation similar to that measured for cromakalim but less potent than this reference drug. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80020-8