1-Carboxy-6-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1-Carboxy-6-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane
• 英文别名: (1R,5S,6S)-6-methyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: ROHGIGWSIUKFCD-VJJSXZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Carboxy-6-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane 在 盐酸 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-Amino-6-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane hydrochloride
  参考文献：
  名称：

  Intramolecular cyclopropanation: stereospecific synthesis of (E)- and (Z)-1-aminocyclopropane-1-carboxylic acids

  摘要：

  tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields. The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclo[3.1.0]hexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 15 via Curtius- or Hoffmann-type rearrangements, respectively. The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40% overall from malonic acid) The free amino acids 12 and 18 can be liberated in two steps.

  DOI：

  10.1021/jo00056a020
• 作为产物：
  描述：

  1-O-but-2-enyl 3-O-tert-butyl propanedioate 在 triethylphosphite copper(I) iodide complex 对甲苯磺酰叠氮 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 1-Carboxy-6-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane
  参考文献：
  名称：

  Intramolecular cyclopropanation: stereospecific synthesis of (E)- and (Z)-1-aminocyclopropane-1-carboxylic acids

  摘要：

  tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields. The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclo[3.1.0]hexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 15 via Curtius- or Hoffmann-type rearrangements, respectively. The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40% overall from malonic acid) The free amino acids 12 and 18 can be liberated in two steps.

  DOI：

  10.1021/jo00056a020