5-Methyl-1-phenyl-2,6,7,8-tetraoxa-bicyclo[3.2.1]octan-4-one O-methyl-oxime | 194022-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methyl-1-phenyl-2,6,7,8-tetraoxa-bicyclo[3.2.1]octan-4-one O-methyl-oxime
• CAS: 194022-17-8
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: NQMVHAMIQIJYQT-UHFFFAOYSA-N

物化性质

• 沸点：
  337.9±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-Methyl-1-phenyl-2,6,7,8-tetraoxa-bicyclo[3.2.1]octan-4-one O-methyl-oxime 在 焦磷酸硫胺素 作用下， 以 氘代氯仿 为溶剂， 反应 1.0h， 生成 Benzoic acid 2-[(Z)-methoxyimino]-3-oxo-butyl ester
  参考文献：
  名称：

  Ozonolyses of Acetylenes:  Trapping of α-Oxo Carbonyl Oxides by Carbonyl Compounds and Stabilization of α-Oxo Ozonides by Derivatizations

  摘要：

  Ozonolyses of 2-butyne (7) or of 3-hexyne (14) in the presence of carbonyl compounds (aldehydes, ketones, acid derivatives) afforded the corresponding mostly labile monocyclic alpha-oxo ozonides (9, 13a, 16), which could be stabilized and, hence, isolated by subsequent conversion into alpha-methoximino derivatives. Ozonolyses of 1,4-diacyloxy-substituted (19) and 1-acyloxy-substituted 2-butynes (27) gave bicyclic ozonides (22, 31) by intramolecular [3 + 2]-cycloadditions of the corresponding carbonyl oxide intermediates (20, 29), These ozonides could also be stabilized by reactions with O-methylhydroxylamine to give O-methyloximes (23c, 32) or with diazomethane to give epoxy ozonides (25, 34).

  DOI：

  10.1021/jo9701795
• 作为产物：
  描述：

  but-2-yn-1-yl benzoate 在 吡啶 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 144.0h， 生成 5-Methyl-1-phenyl-2,6,7,8-tetraoxa-bicyclo[3.2.1]octan-4-one O-methyl-oxime
  参考文献：
  名称：

  Ozonolyses of Acetylenes:  Trapping of α-Oxo Carbonyl Oxides by Carbonyl Compounds and Stabilization of α-Oxo Ozonides by Derivatizations

  摘要：

  Ozonolyses of 2-butyne (7) or of 3-hexyne (14) in the presence of carbonyl compounds (aldehydes, ketones, acid derivatives) afforded the corresponding mostly labile monocyclic alpha-oxo ozonides (9, 13a, 16), which could be stabilized and, hence, isolated by subsequent conversion into alpha-methoximino derivatives. Ozonolyses of 1,4-diacyloxy-substituted (19) and 1-acyloxy-substituted 2-butynes (27) gave bicyclic ozonides (22, 31) by intramolecular [3 + 2]-cycloadditions of the corresponding carbonyl oxide intermediates (20, 29), These ozonides could also be stabilized by reactions with O-methylhydroxylamine to give O-methyloximes (23c, 32) or with diazomethane to give epoxy ozonides (25, 34).

  DOI：

  10.1021/jo9701795