(1S,4R,7R,8S)-1-amino-7,8-O-cyclohexylidene-7,8-dihydroxy-2,5-dioxa-bicyclo<2.2.2>octan-6-one | 150496-27-8

• 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: (1S,4R,7R,8S)-1-amino-7,8-O-cyclohexylidene-7,8-dihydroxy-2,5-dioxa-bicyclo<2.2.2>octan-6-one
• 英文别名: (1S,2R,6R,7R)-1-aminospiro[3,5,8,10-tetraoxatricyclo[5.2.2.02,6]undecane-4,1'-cyclohexane]-9-one
• CAS: 150496-27-8
• 化学式: C₁₂H₁₇NO₅
• 分子量: 255.271
• InChiKey: LLOAGOFCZYRSNZ-HNBLOZHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4R,7R,8S)-1-amino-7,8-O-cyclohexylidene-7,8-dihydroxy-2,5-dioxa-bicyclo<2.2.2>octan-6-one 在 potassium tert-butylate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 (-)-5-epi-hydantocidin
  参考文献：
  名称：

  Synthesis of 1-epihydantocidin from d-ribose

  摘要：

  A key step in a short synthesis of 1-epihydantocidin (2) is the unanticipated transformation of azidolactones (8) and (10) to a bicyclic amine (12) induced by tetra-n-propyl-ammonium perruthenate in the presence of morpholine-N-oxide. The structure of (12) was established by X-ray crystallographic analysis.

  DOI：

  10.1016/s0040-4039(00)73695-1
• 作为产物：
  描述：

  6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2-O-trifluoromethanesulfonyl-D-altrono-1,5-lactone 在 N-morpholine oxide 、 sodium azide 、 四丙基高钌酸铵 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.17h， 生成 (1S,4R,7R,8S)-1-amino-7,8-O-cyclohexylidene-7,8-dihydroxy-2,5-dioxa-bicyclo<2.2.2>octan-6-one
  参考文献：
  名称：

  Synthesis of 1-epihydantocidin from d-ribose

  摘要：

  A key step in a short synthesis of 1-epihydantocidin (2) is the unanticipated transformation of azidolactones (8) and (10) to a bicyclic amine (12) induced by tetra-n-propyl-ammonium perruthenate in the presence of morpholine-N-oxide. The structure of (12) was established by X-ray crystallographic analysis.

  DOI：

  10.1016/s0040-4039(00)73695-1

文献信息

• Synthesis of 5- epi hydantocidin from D-ribose
  作者：Antony J. Fairbanks、George W.J. Fleet

  DOI：10.1016/0040-4020(95)00110-t

  日期：1995.3

  Tetra-n-propyl ammonium perruthenate in the presence of morpholine-N-oxide induced the unanticipated transformation of the epimeric alpha-azido-1,4-lactones 4 into the bicyclic amine 3 and provided the key step in the synthesis of 5-epihydantocidin 2. Brief investigations into the acid catalysed equilibration of hydantocidin 1 and 5-epihydantocidin 2 are described.