3-nitro-5-phenyl-4,5-dihydro-isoxazole 2-oxide | 10313-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-nitro-5-phenyl-4,5-dihydro-isoxazole 2-oxide
• 英文别名: 3-nitro-2-oxido-5-phenyl-4,5-dihydro-1,2-oxazol-2-ium
• CAS: 10313-10-7
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: MNNQTMLNFKXDPP-UHFFFAOYSA-N

物化性质

• 沸点：
  392.5±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 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：
  0.22
• 拓扑面积：
  78.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-nitro-5-phenyl-4,5-dihydro-isoxazole 2-oxide 、 乙烯 以 苯 为溶剂， 50.0 ℃ 、3.04 MPa 条件下， 生成 3a-nitro-2-phenyl-tetrahydro-isoxazolo[2,3-b]isoxazole
  参考文献：
  名称：

  Tartakovskii,V.A. et al., Journal of Organic Chemistry USSR (English Translation), 1966, vol. 2, p. 2183 - 2188

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙烯 、 四硝基甲烷 以 二氯甲烷 为溶剂， 反应 2.45h， 以31.2%的产率得到
  参考文献：
  名称：

  Photochemical Nitration by Tetranitromethane. Part XLIII. Photolysis of Some Styrene Derivatives with Tetranitromethane: Mechanism of Isoxazolidine Formation.

  摘要：

  The photochemical reaction of tetranitromethane in dichloromethane or acetonitrile with 4-methylstyrene (2a), styrene (2b), 4-chlorostyrene (2c), 3-chlorostyrene (2d) or 4-acetoxystyrene (2e) gives two stereoisomeric isoxazolidines, 2-(2'-nitro-1'-X-phenyl)ethoxy-3,3-dinitro-5-(X-phenyl)isoxazolidine (3 and 4, X=4-Me, H, 4-Cl, 3-Cl or 4-AcO), a nitro ketone, nitromethyl X-phenyl ketone (5, X=4-Me, H, 4-Cl, 3-Cl or 4-AcO) and a nitronic ester, 3-nitro-5-(X-phenyl)-2-isoxazoline N-oxide (6, X=4-Me, H, 4-Cl or 4-AcO). In each case, the (RS,RS)-stereoisomer 4 is the major isoxazolidine formed.The first step of the reaction is the photogeneration of the triad [2(.+) NO2 (NO2)(3)C-]. In the formation of isoxazolidines 3 and 4, and of the nitronic esters 6, the key intermediate is assumed to be the substituted aminoxyl, 3,3-dinitro-4-(X-phenyl)isoxazolidin-N-oxyl (8, X=4-Me, H, 4-Cl, 3-Cl or 4-AcO) formed by reaction of the substituted styrene radical cation (2(.+)) with trinitromethanide ion followed by cyclization of the resulting carbon radical 7. Loss of nitrogen dioxide from 8 gives nitronic esters 6, and trapping of the 1-(X-phenyl)-2-nitroethyl radical, formed by addition of NO2 at the beta-carbon of 2, by aminoxyl 8, gives the isoxazolidines 3 and 4 directly.

  DOI：

  10.3891/acta.chem.scand.52-0751