1-(5-甲氧基-3-甲基-1,2,4-三四氢呋喃-3-基)乙酮 | 194021-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 中文名称: 1-(5-甲氧基-3-甲基-1,2,4-三四氢呋喃-3-基)乙酮
• 英文名称: 3-acetyl-5-methoxy-3-methyl-1,2,4-trioxolane
• 英文别名: 1-(5-Methoxy-3-methyl-1,2,4-trioxolan-3-yl)ethanone
• CAS: 194021-88-0
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: FSAAIWWCJBCQHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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 、 1-(5-甲氧基-3-甲基-1,2,4-三四氢呋喃-3-基)乙酮 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以7%的产率得到1-(5-Methoxy-3-methyl-[1,2,4]trioxolan-3-yl)-ethanone 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：

  2-丁炔 、 甲酸甲酯 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以12%的产率得到1-(5-甲氧基-3-甲基-1,2,4-三四氢呋喃-3-基)乙酮
  参考文献：
  名称：

  Short path syntheses of α-diozonides by sequential ozonolyses of acetylenes and O-methyl oximes

  摘要：

  在添加了羰基化合物 3 的情况下，丁-2-炔 1 发生臭氧分解，生成 δ-oxo 臭氧化合物 4。随后，臭氧化物 4 与 O-甲基环己酮肟的臭氧分解在原位生成的环己酮氧化物 6 发生环加成反应，生成δ-±-二臭氧化物 7，其中包含了所涉及的所有三种底物的碳骨架。酰氧基取代的丁-2-炔 9 的臭氧分解生成相应的双环δ-氧代臭氧化物 11，随后与 6 发生类似的环化反应，生成相应的δ-二臭氧化物 12。对结晶二氮杂环酰胺 12a 的 X 射线晶体分析表明，它完全是由 6 与 11a 进行外加生成的。

  DOI：

  10.1039/a700989e

文献信息

• Short path syntheses of α-diozonides by sequential ozonolyses of acetylenes and O-methyl oximes
  作者：Yuxiang Dong、Karl Griesbaum、Kevin J. McCullough

  DOI：10.1039/a700989e

  日期：——

  Ozonolyses of but-2-yne 1 in the presence of added carbonyl compounds 3 afford α-oxo ozonides 4. Subsequent cycloadditions between ozonides 4 and cyclohexanone oxide 6, generated in situ by ozonolysis of O-methylcyclohexanone oxime, yield in turn α-diozonides 7 into which have been incorporated the carbon skeletons of all three substrates involved. Ozonolyses of acyloxy-substituted but-2-ynes 9 yield the corresponding bicyclic α-oxo ozonides 11 which subsequently participate in analogous cycloadditions with 6 to produce the corresponding α-diozonides 12. X-Ray crystallographic analysis of the crystalline diozonide 12a shows that it has been formed exclusively by exo-addition of 6 to 11a.

  在添加了羰基化合物 3 的情况下，丁-2-炔 1 发生臭氧分解，生成 δ-oxo 臭氧化合物 4。随后，臭氧化物 4 与 O-甲基环己酮肟的臭氧分解在原位生成的环己酮氧化物 6 发生环加成反应，生成δ-±-二臭氧化物 7，其中包含了所涉及的所有三种底物的碳骨架。酰氧基取代的丁-2-炔 9 的臭氧分解生成相应的双环δ-氧代臭氧化物 11，随后与 6 发生类似的环化反应，生成相应的δ-二臭氧化物 12。对结晶二氮杂环酰胺 12a 的 X 射线晶体分析表明，它完全是由 6 与 11a 进行外加生成的。
• 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).