6-methyl-2-(methylthio)-3-nitro-4H-chromen-4-one | 1264701-68-9

• 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-methyl-2-(methylthio)-3-nitro-4H-chromen-4-one
• 英文别名: 6-Methyl-2-methylsulfanyl-3-nitrochromen-4-one
• CAS: 1264701-68-9
• 化学式: C₁₁H₉NO₄S
• 分子量: 251.263
• InChiKey: RCQHQHQTBOZGCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-乙基哌嗪 、 6-methyl-2-(methylthio)-3-nitro-4H-chromen-4-one 以 1,4-二氧六环 为溶剂， 以91%的产率得到6-methyl-2-(4-ethylpiperazin-1-yl)-3-nitro-4H-chromen-4-one
  参考文献：
  名称：

  A concise synthetic strategy to functionalized chromenones via [5+1] heteroannulation and facile C–N/C–S/C–O bond formation with various nucleophiles

  摘要：

  A highly efficient strategy to 2,3-substituted chromen-4H-ones has been developed. The methodology involves unexpected intramolecular heteroannulation of readily accessible substituted 2-hydroxy-omega-nitroacetophenone with carbon disulfide in the presence K2CO3 followed by methylation with methyl iodide. These chromenones were further reacted with various nucleophiles such as amines, thiols, and alkoxide resulting in the facile C-N, C-S, and C-O bond formation. The scope and generality have been discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.020
• 作为产物：
  描述：

  二硫化碳 、 2-Hydroxy-5-methyl-ω-nitroacetophenon 、 碘甲烷 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以84%的产率得到6-methyl-2-(methylthio)-3-nitro-4H-chromen-4-one
  参考文献：
  名称：

  A concise synthetic strategy to functionalized chromenones via [5+1] heteroannulation and facile C–N/C–S/C–O bond formation with various nucleophiles

  摘要：

  A highly efficient strategy to 2,3-substituted chromen-4H-ones has been developed. The methodology involves unexpected intramolecular heteroannulation of readily accessible substituted 2-hydroxy-omega-nitroacetophenone with carbon disulfide in the presence K2CO3 followed by methylation with methyl iodide. These chromenones were further reacted with various nucleophiles such as amines, thiols, and alkoxide resulting in the facile C-N, C-S, and C-O bond formation. The scope and generality have been discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.020