6-nitro-4-(phenylthio)benzo[d]isoxazole-3-carboxaldehyde O-methyloxime | 369390-06-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-nitro-4-(phenylthio)benzo[d]isoxazole-3-carboxaldehyde O-methyloxime
• 英文别名: 6-nitro-4-phenylthiobenzo[d]isoxazole-3-carbaldehyde O-methyloxime
• CAS: 369390-06-7
• 化学式: C₁₅H₁₁N₃O₄S
• 分子量: 329.336
• InChiKey: GJNJWQRUAXXUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.76
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-nitro-4-(phenylthio)benzo[d]isoxazole-3-carboxaldehyde O-methyloxime 在 双氧水 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.0h， 以91%的产率得到6-nitro-4-(phenylsulfonyl)benzo[d]isoxazole-3-carboxaldehyde O-methyloxime
  参考文献：
  名称：

  摘要：

  Oxidation of 3-substituted 4-R-6-nitro-1-phenyl-1H-indazoles and benzo[d]isoxazoles (R = Ph, CH2CO2Me) gave the corresponding sulfones treatment of which with PhSH-K2CO3 in N-methylpyrrolidone results in replacement of only the RSO2 group in position 4 with the 6-NO2 group remaining intact, contrary to the known sequence of nucleophilic substitution for meta-arranged nucleofuges.

  DOI：

  10.1023/a:1026012922607
• 作为产物：
  描述：

  2-oximino-2,4,6-trinitrophenylacetaldehyde 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 乙醇 为溶剂， 反应 51.0h， 生成 6-nitro-4-(phenylthio)benzo[d]isoxazole-3-carboxaldehyde O-methyloxime
  参考文献：
  名称：

  摘要：

  A new procedure was developed for the preparation of 4,6-dinitro-3-R-benzo[d]isoxazoles (R are derivatives of the aldehyde group) based on 2,4,6-trinitrophenylacetaldehyde. The resulting compounds are characterized by the regiospecific substitution of the nitro group at position 4 under the action of anionic nucleophiles RS-, RO-, F-, or N-3(-), Which allowed the development of a new method for the preparation of previously unknown 4-Nu-6-nitro-3-R-benzo[d]isoxazoles (Nu is the residue of a nucleophile). At the same time, oxidative nucleophilic substitution under the action of anions of some beta -dicarbonyl compounds leads to the replacement of the hydrogen atom at position 7 with the corresponding C-nucleophiles.

  DOI：

  10.1023/a:1011313324497