Cyclododecyl (p-methoxybenzoyl)formate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Cyclododecyl (p-methoxybenzoyl)formate
• 英文别名: Cyclododecyl 2-(4-methoxyphenyl)-2-oxoacetate
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: KKQWHTJXOKDDGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cyclododecyl (p-methoxybenzoyl)formate 以 苯 为溶剂， 反应 4.25h， 生成 4-甲氧基苯甲醛 、 环十二酮 、 大茴香酸
  参考文献：
  名称：

  Photochemistry of Substituted Benzoylformate Esters. A Convenient Method for the Photochemical Oxidation of Alcohols

  摘要：

  The production of aldehydes and ketones via photochemical hydrogen atom transfer in substituted benzoylformate esters of primary and secondary alcohols has been investigated. Substituent effect studies have shown that (2,4-dimethoxybenzoyl)formate (DMBF) esters give superior performance. A divergence in the byproducts derived from the ester group (the benzaldehyde (and presumably CO) or the benzoic acid (and presumably CO2)) is observed depending on the presence of oxygen. A mechanistic rationale for the formation of the benzoic acid has been advanced based on the known trapping of intermediate 1,4-biradicals by oxygen followed by fragmentation.

  DOI：

  10.1021/jo00113a029
• 作为产物：
  描述：

  环十二醇 、 对甲氧基苯乙醛酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到Cyclododecyl (p-methoxybenzoyl)formate
  参考文献：
  名称：

  Photochemistry of Substituted Benzoylformate Esters. A Convenient Method for the Photochemical Oxidation of Alcohols

  摘要：

  The production of aldehydes and ketones via photochemical hydrogen atom transfer in substituted benzoylformate esters of primary and secondary alcohols has been investigated. Substituent effect studies have shown that (2,4-dimethoxybenzoyl)formate (DMBF) esters give superior performance. A divergence in the byproducts derived from the ester group (the benzaldehyde (and presumably CO) or the benzoic acid (and presumably CO2)) is observed depending on the presence of oxygen. A mechanistic rationale for the formation of the benzoic acid has been advanced based on the known trapping of intermediate 1,4-biradicals by oxygen followed by fragmentation.

  DOI：

  10.1021/jo00113a029