Acetic acid 1-methyl-4-oxo-2,6,7,8-tetraoxa-bicyclo[3.2.1]oct-5-ylmethyl ester | 194022-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid 1-methyl-4-oxo-2,6,7,8-tetraoxa-bicyclo[3.2.1]oct-5-ylmethyl ester
• 英文别名: (1-Methyl-4-oxo-2,6,7,8-tetraoxabicyclo[3.2.1]octan-5-yl)methyl acetate
• CAS: 194022-11-2
• 化学式: C₈H₁₀O₇
• 分子量: 218.163
• InChiKey: ZPJMMWQCUKNXJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid 1-methyl-4-oxo-2,6,7,8-tetraoxa-bicyclo[3.2.1]oct-5-ylmethyl ester 在 吡啶 、 焦磷酸硫胺素 作用下， 以 甲醇 、 氘代氯仿 为溶剂， 反应 124.0h， 生成 Acetic acid 4-acetoxy-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：

  1,4-二乙酰氧基-2-丁炔 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到Acetic acid 1-methyl-4-oxo-2,6,7,8-tetraoxa-bicyclo[3.2.1]oct-5-ylmethyl 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