1-(tert-Butoxycarbonyl)-1-<(tert-butoxycarbonyl)amino>-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3,3-dimethylcyclopropane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(tert-Butoxycarbonyl)-1-<(tert-butoxycarbonyl)amino>-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3,3-dimethylcyclopropane
• 英文别名: tert-butyl (1S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• 化学式: C₂₂H₄₃NO₅Si
• 分子量: 429.673
• InChiKey: UXBGRXNENZDBAF-OYHNWAKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(tert-Butoxycarbonyl)-1-<(tert-butoxycarbonyl)amino>-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3,3-dimethylcyclopropane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到1-(tert-Butoxycarbonyl)-1-<(tert-butoxycarbonyl)amino>-2-(hydroxymethyl)-3,3-dimethylcyclopropane
  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-(tert-Butoxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3,3-dimethylcyclopropanecarboxamide 、 叔丁醇 在 吡啶 、 lead(IV) acetate 作用下， 以43%的产率得到1-(tert-Butoxycarbonyl)-1-<(tert-butoxycarbonyl)amino>-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3,3-dimethylcyclopropane
  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