2,8-dimethyl-4-oxo-4H-3,1-benzoxazine-6-carbonitrile | 1353868-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2,8-dimethyl-4-oxo-4H-3,1-benzoxazine-6-carbonitrile
• 英文别名: 2,8-Dimethyl-4-oxo-3,1-benzoxazine-6-carbonitrile；2,8-dimethyl-4-oxo-3,1-benzoxazine-6-carbonitrile
• CAS: 1353868-36-6
• 化学式: C₁₁H₈N₂O₂
• 分子量: 200.197
• InChiKey: VIORXYHCVNGOAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,8-dimethyl-4-oxo-4H-3,1-benzoxazine-6-carbonitrile 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Bioactivities Evaluation of Novel N-Pyridylpyrazole Derivatives with 1,2,3-Triazole and Quinazolin-4(3H)-one Substructures

  摘要：

  Two series of N-pyridylpyrazole derivatives containing 1,2,3-triazole and quinazolin-4(3H)-one substructures were designed and synthesized. In total, 18 novel compounds were prepared, and all compounds were characterized by H-1 NMR, C-13 NMR and elemental analysis (EA). Preliminary bioassay results revealed that a few of new compounds with quinazolin-4(3H)-one moiety exhibited good insecticidal activity against the oriental armyworm (Mythimna separata). In addition, the compounds Ia-h with 1, 2, 3-triazole moiety showed broad-spectrum antifungal activities against Fusarium oxysporum f.sp.cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 [mu g/mL concentration. The EC50 values of Ib and If against Botryosphaeria dothidea were 13.9 and 11.0 mu g/mL, respectively, which were comparable to Chlorothalonil. These results indicated the potential application of N-pyridylpyrazole derivatives as fungicide in further study.

  DOI：

  10.3987/com-18-13944
• 作为产物：
  描述：

  2-氨基-5-碘-3-甲基苯羧酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.0h， 生成 2,8-dimethyl-4-oxo-4H-3,1-benzoxazine-6-carbonitrile
  参考文献：
  名称：

  苯并嗪酮的亲核开环反应－获得邻氨基-2,2,2-三氟苯乙酮的途径

  摘要：

  有机氟化合物在现代药物发现和材料科学中备受关注。我们在本文中报道了从商业上可获得的邻氨基苯甲酸开始的对o-氨基-2,2,2-三氟苯乙酮的新的合成途径，其可以容易地转化为相应的苯并恶嗪酮。在第二步骤中，在酸性处理后，通过添加Ruppert's试剂形成三氟甲基化的酮。

  DOI：

  10.1016/j.tetlet.2011.11.014

文献信息

• Synthesis and Bioactivities Evaluation of Novel N-Pyridylpyrazole Derivatives with 1,2,3-Triazole and Quinazolin-4(3H)-one Substructures
  作者：Yunyun Zhou、Zhengming Li、Wei Wei、Liangliang Zhu

  DOI：10.3987/com-18-13944

  日期：——

  Two series of N-pyridylpyrazole derivatives containing 1,2,3-triazole and quinazolin-4(3H)-one substructures were designed and synthesized. In total, 18 novel compounds were prepared, and all compounds were characterized by H-1 NMR, C-13 NMR and elemental analysis (EA). Preliminary bioassay results revealed that a few of new compounds with quinazolin-4(3H)-one moiety exhibited good insecticidal activity against the oriental armyworm (Mythimna separata). In addition, the compounds Ia-h with 1, 2, 3-triazole moiety showed broad-spectrum antifungal activities against Fusarium oxysporum f.sp.cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 [mu g/mL concentration. The EC50 values of Ib and If against Botryosphaeria dothidea were 13.9 and 11.0 mu g/mL, respectively, which were comparable to Chlorothalonil. These results indicated the potential application of N-pyridylpyrazole derivatives as fungicide in further study.
• Nucleophilic ring-opening reaction of benzoxazinones—access to o-amino-2,2,2-trifluoroacetophenones
  作者：Nadine Allendörfer、Mazen Es-Sayed、Martin Nieger、Stefan Bräse

  DOI：10.1016/j.tetlet.2011.11.014

  日期：2012.1

  We herein report a new synthetic access to o-amino-2,2,2-trifluoroacetophenones starting from commercially available o-amino benzoic acids, which can easily be converted into the corresponding benzoxazinones. In a second step the trifluoromethylated ketone is formed via addition of Ruppert’s reagent following acidic work up.

  有机氟化合物在现代药物发现和材料科学中备受关注。我们在本文中报道了从商业上可获得的邻氨基苯甲酸开始的对o-氨基-2,2,2-三氟苯乙酮的新的合成途径，其可以容易地转化为相应的苯并恶嗪酮。在第二步骤中，在酸性处理后，通过添加Ruppert's试剂形成三氟甲基化的酮。