3-ethoxycarbonyl-4-methoxycarbonyl-1-methylpyrano<2,3-c>pyrazol-6(1H)-one | 81292-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-ethoxycarbonyl-4-methoxycarbonyl-1-methylpyrano<2,3-c>pyrazol-6(1H)-one
• 英文别名: 3-ethoxycarbonyl-4-methoxycarbonyl-1-methylpyrano[2,3-c]pyrazol-6(1H)-one；3-O-ethyl 4-O-methyl 1-methyl-6-oxopyrano[2,3-c]pyrazole-3,4-dicarboxylate
• CAS: 81292-15-1
• 化学式: C₁₂H₁₂N₂O₆
• 分子量: 280.237
• InChiKey: VQLDQOXBPBKECM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  100.63
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  Ethyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate 、 丁炔二酸二甲酯 以11%的产率得到
  参考文献：
  名称：

  UEDA, TAISEI;MASE, HIDESHI;ODA, NORIICHI;ITO, ISOO, CHEM. AND PHARM. BULL., 1981, 29, N 12, 3522-3528

  摘要：

  DOI：

文献信息

• Synthesis of pyrazolone derivatives. XXXIX. Synthesis and analgesic activity of pyrano(2,3-c)pyrazoles.
  作者：TAISEI UEDA、HIDESHI MASE、NORIICHI ODA、ISOO ITO

  DOI：10.1248/cpb.29.3522

  日期：——

  Syntheses of pyrano [2, 3-c] pyrazoles by means of the reaction of 3-ethoxycarbonyl-5-hydroxy-1-methyl (or phenyl) pyrazole (Ia, b) and acetylenecarboxylates or ethyl acetoacetate were examined. The reactions of Ia, b with acetylenecarboxylates gave 3-ethoxycarbonyl-4-substituted-1-methyl (or phenyl) pyrano [2, 3-c] pyrazol-6 (1H)-ones (IIa-c) in 5.9-23.9% yields. The Pechmann-Duisberg reaction of Ia-c with ethyl acetoacetate gave 3-ethoxycarbonyl-4-methyl-1-substitutedpyrano [2, 3-c] pyrazol-6 (1H)-ones (VIIa-c) in 33.1-46.2% yields. Similar reactions of 5-hydroxy-3-methylcarbamoyl-1-phenyl (or m-chlorophenyl) pyrazoles (IXa, b) with ethyl acetoacetate gave 4-methyl-3-methylcarbamoyl-1-phenyl (or m-chlorophenyl) pyrano [2, 3-c] pyrazol-6 (1H)-ones (Xa, b) in 17.4-30% yields. The newly synthesized pyrano [2, 3-c] pyrazoles (Xa, Xb, XII) showed analgesic activity in mice when tested by two methods.

  研究了通过 3-乙氧羰基-5-羟基-1-甲基（或苯基）吡唑（Ia, b）与乙炔羧酸酯或乙酰乙酸乙酯反应合成吡喃并[2, 3-c]吡唑的方法。Ia, b 与乙炔羧酸酯反应生成 3-乙氧羰基-4-取代-1-甲基（或苯基）吡喃并[2, 3-c] 吡唑-6 (1H)-酮（IIa-c），产率为 5.9-23.9%。Ia-c 与乙酰乙酸乙酯的 Pechmann-Duisberg 反应生成 3-乙氧羰基-4-甲基-1-取代的吡喃并[2，3-c] 吡唑-6 (1H)-酮（VIIa-c），收率为 33.1-46.2%。5-hydroxy-3-methylcarbamoyl-1-phenyl (or m-chlorophenyl) pyrazoles (IXa, b) 与乙酰乙酸乙酯发生类似反应，得到 4-methyl-3-methylcarbamoyl-1-phenyl (or m-chlorophenyl) pyrano [2, 3-c] pyrazol-6 (1H)-ones (Xa, b)，收率为 17.4-30%。新合成的吡喃并[2，3-c]吡唑（Xa、Xb、XII）通过两种方法对小鼠进行了镇痛活性测试。