5-ethoxy-3-ethyl-3-propionyl-1,2,4-trioxolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: 5-ethoxy-3-ethyl-3-propionyl-1,2,4-trioxolane
• 英文别名: 1-(5-Ethoxy-3-ethyl-1,2,4-trioxolan-3-yl)propan-1-one
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: QVAZMARWDVIJKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氯苯甲酰乙腈 、 5-ethoxy-3-ethyl-3-propionyl-1,2,4-trioxolane 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 144.0h， 生成 1-(5-Ethoxy-3-ethyl-[1,2,4]trioxolan-3-yl)-propan-1-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
• 作为产物：
  描述：

  3-己炔 、 甲酸乙酯 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到5-ethoxy-3-ethyl-3-propionyl-1,2,4-trioxolane
  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

文献信息

• Ozonolyses of Acetylenes:  Trapping of α-Oxo Carbonyl Oxides by Carbonyl Compounds and Stabilization of α-Oxo Ozonides by Derivatizations
  作者：Karl Griesbaum、Yuxiang Dong、Kevin J. McCullough

  DOI：10.1021/jo9701795

  日期：1997.9.1

  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).