6-Nitrocoumarin hydrazone | 231290-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-Nitrocoumarin hydrazone
• CAS: 231290-51-0
• 化学式: C₉H₇N₃O₃
• 分子量: 205.173
• InChiKey: GOUYGCOTHQKVTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-Nitrocoumarin hydrazone 以 苯 为溶剂， 反应 9.0h， 生成 N,N'-di[2-Imino-benzopyrane(6-nitro-benzopyrane)]piperazine-2,3,5,6-tetraone
  参考文献：
  名称：

  Synthesis of some new biologically-active coumarin derivatives

  摘要：

  Coumarin and 6-nitrocoumarin hydrazones (2a,b), respectively, were prepared via the reaction of 2-thiocoumarin (1a,b) derivatives with hydrazine hydrate. The hydrazones were used as key intermediates for the preparation of some benzopyrano[2,3-c]pyrazoles (21-24) through the reaction of different acyl halides and subsequent cyclization in N,N-dimethylaniline. Benzopyrano[2,3-c]pyrazole-3-thione (25a,b) was prepared by the reaction of 1a with CS2 on which some alkylation, acylation and Mannich reactions were studied. Alternative procedures, other reactions and biological activity of some new compounds were given.

  DOI：

  10.1016/s0014-827x(98)00099-8
• 作为产物：
  描述：

  6-nitro-chromene-2-thione 在 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 13.0h， 以90%的产率得到6-Nitrocoumarin hydrazone
  参考文献：
  名称：

  Synthesis of some new biologically-active coumarin derivatives

  摘要：

  Coumarin and 6-nitrocoumarin hydrazones (2a,b), respectively, were prepared via the reaction of 2-thiocoumarin (1a,b) derivatives with hydrazine hydrate. The hydrazones were used as key intermediates for the preparation of some benzopyrano[2,3-c]pyrazoles (21-24) through the reaction of different acyl halides and subsequent cyclization in N,N-dimethylaniline. Benzopyrano[2,3-c]pyrazole-3-thione (25a,b) was prepared by the reaction of 1a with CS2 on which some alkylation, acylation and Mannich reactions were studied. Alternative procedures, other reactions and biological activity of some new compounds were given.

  DOI：

  10.1016/s0014-827x(98)00099-8

文献信息

• SYNTHETIC AND BIOLOGICAL STUDIES ON COUMARIN HYDRAZONE DERIVATIVES
  作者：A. M. El-sayed、O. A. Abd Allah

  DOI：10.1080/10426500108040586

  日期：2001.3.1

  Abstract The reaction of both of coumarin and 6-nitrocoumarin hydrazones (1,4) with alkyl(aryl)isothiocyanate afforded the corresponding 3-N[alkyl(aryl)thioamido] coumarins 3a-d or benzopyrano[2,3-c]pyrazole-3-thione derivatives 6a-d , respectively. Compounds (3a-d) were used as key intermediates for the preparation of benzopyrano-pyridine derivatives (7a-d & 10a) or benzopyranoazepine derivatives 8a,c &

  摘要 香豆素和 6-硝基香豆素腙 (1,4) 与烷基（芳基）异硫氰酸酯反应得到相应的 3-N[烷基（芳基）硫代氨基]香豆素 3a-d 或苯并吡喃并[2,3-c]吡唑-3-硫酮衍生物 6a-d 分别。化合物（3a-d）被用作关键中间体，用于通过与不同酰卤或乙氧基亚甲基丙二腈反应并随后环化制备苯并吡喃-吡啶衍生物（7a-d和10a）或苯并吡喃氮杂衍生物8a、c和12a-d。给出了一些新化合物对革兰氏+ve和革兰氏-ve的生物活性。