3-methoxy-6-oxoheptanoic acid | 1360432-65-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-methoxy-6-oxoheptanoic acid
• CAS: 1360432-65-0
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: MHOXCEPVOAFRIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-6-oxoheptanoic acid 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到2-methoxy-5-methyl-6-oxabicyclo[3.2.0]heptan-7-one
  参考文献：
  名称：

  A Diastereoselective, Nucleophile-Promoted Aldol-Lactonization of Ketoacids Leading to Bicyclic-β-Lactones

  摘要：

  An improved, tandem acid activation/aldol-lactonization process is described. This more practical protocol shortens reaction times for the construction of bicyclic beta-lactones from ketoacids and implements the use of commercially available reagents p-toluenesulfonyl chloride (p-TsC1) as activator and 4-dimethylaminopyridine (4-DMAP) as nucleophllic promoter (Lewis base). Substrates with beta-substituents, with respect to the carboxylic acid, consistently showed excellent levels of diastereoselectivity during the bis-cyclization event.

  DOI：

  10.1021/jo202252y
• 作为产物：
  描述：

  3-hydroxy-6-methyl-6-heptenoic acid ethyl ester 在 甲醇 、 二甲基硫 、 氧气 、 1,8-双二甲氨基萘 、 臭氧 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 3-methoxy-6-oxoheptanoic acid
  参考文献：
  名称：

  A Diastereoselective, Nucleophile-Promoted Aldol-Lactonization of Ketoacids Leading to Bicyclic-β-Lactones

  摘要：

  An improved, tandem acid activation/aldol-lactonization process is described. This more practical protocol shortens reaction times for the construction of bicyclic beta-lactones from ketoacids and implements the use of commercially available reagents p-toluenesulfonyl chloride (p-TsC1) as activator and 4-dimethylaminopyridine (4-DMAP) as nucleophllic promoter (Lewis base). Substrates with beta-substituents, with respect to the carboxylic acid, consistently showed excellent levels of diastereoselectivity during the bis-cyclization event.

  DOI：

  10.1021/jo202252y