(1R,2R,6S,7R)-4,4-Dimethyl-3,5-dioxa-8,11-diaza-tricyclo[5.3.1.0^2,6]undec-8-ene-11-carboxylic acid tert-butyl ester | 599199-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,2R,6S,7R)-4,4-Dimethyl-3,5-dioxa-8,11-diaza-tricyclo[5.3.1.0^2,6]undec-8-ene-11-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (1R,2R,6S,7R)-4,4-dimethyl-3,5-dioxa-8,11-diazatricyclo[5.3.1.02,6]undec-8-ene-11-carboxylate
• CAS: 599199-70-9
• 化学式: C₁₄H₂₂N₂O₄
• 分子量: 282.34
• InChiKey: ZCIAAVFXXSYJAG-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,6S,7R)-4,4-Dimethyl-3,5-dioxa-8,11-diaza-tricyclo[5.3.1.0^2,6]undec-8-ene-11-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以97%的产率得到(1R,2R,6S,7R)-4,4-Dimethyl-3,5-dioxa-8,11-diaza-tricyclo[5.3.1.0^2,6]undecane-11-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Regioselective rearrangement of 7-azabicyclo[2.2.1]hept-2-aminyl radicals: first synthesis of 2,8-diazabicyclo[3.2.1]oct-2-enes and their conversion into 5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidines, new inhibitors of α-mannosidases

  摘要：

  Enantiomerically pure 2,8-diazabicyclo[3.2.1]oct-2-ene derivatives (+)-5 and (-)-5 have been obtained from 2-azido-3-tosyl-7-azabicyclo[2.2.1]heptanes (+)-1 and (-)-2 and their enantiomers, by ring expansion under radical conditions. Compounds (+)-5 and (-)-5 were transformed into hemiaminals 9 ((3S,4R,5R)- and 10 ((3R,4S,5S)-5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidine) that are good inhibitors of alpha-mannosidases. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01141-9
• 作为产物：
  描述：

  (+)-(1S,2R,3S,4S,5S,6R)-5-endo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-exo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以40%的产率得到(1R,2R,6S,7R)-4,4-Dimethyl-3,5-dioxa-8,11-diaza-tricyclo[5.3.1.0^2,6]undec-8-ene-11-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Regioselective rearrangement of 7-azabicyclo[2.2.1]hept-2-aminyl radicals: first synthesis of 2,8-diazabicyclo[3.2.1]oct-2-enes and their conversion into 5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidines, new inhibitors of α-mannosidases

  摘要：

  Enantiomerically pure 2,8-diazabicyclo[3.2.1]oct-2-ene derivatives (+)-5 and (-)-5 have been obtained from 2-azido-3-tosyl-7-azabicyclo[2.2.1]heptanes (+)-1 and (-)-2 and their enantiomers, by ring expansion under radical conditions. Compounds (+)-5 and (-)-5 were transformed into hemiaminals 9 ((3S,4R,5R)- and 10 ((3R,4S,5S)-5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidine) that are good inhibitors of alpha-mannosidases. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01141-9

文献信息

• Regioselective rearrangement of 7-azabicyclo[2.2.1]hept-2-aminyl radicals: first synthesis of 2,8-diazabicyclo[3.2.1]oct-2-enes and their conversion into 5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidines, new inhibitors of α-mannosidases
  作者：Antonio J Moreno-Vargas、Pierre Vogel

  DOI：10.1016/s0040-4039(03)01141-9

  日期：2003.6

  Enantiomerically pure 2,8-diazabicyclo[3.2.1]oct-2-ene derivatives (+)-5 and (-)-5 have been obtained from 2-azido-3-tosyl-7-azabicyclo[2.2.1]heptanes (+)-1 and (-)-2 and their enantiomers, by ring expansion under radical conditions. Compounds (+)-5 and (-)-5 were transformed into hemiaminals 9 ((3S,4R,5R)- and 10 ((3R,4S,5S)-5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidine) that are good inhibitors of alpha-mannosidases. (C) 2003 Published by Elsevier Science Ltd.