(2R,3R,4R,5R)-3,4-O-cyclohexylidene-6,8-diaza-3,4-dihydroxy-2-hydroxymethyl-1-oxaspiro<4.4>nonan-7,9-dione | 150496-29-0

• 分子结构分类: 有机化合物
• 英文名称: (2R,3R,4R,5R)-3,4-O-cyclohexylidene-6,8-diaza-3,4-dihydroxy-2-hydroxymethyl-1-oxaspiro<4.4>nonan-7,9-dione
• CAS: 150496-29-0
• 化学式: C₁₃H₁₈N₂O₆
• 分子量: 298.296
• InChiKey: FZGBJKMTSHYGNN-WBPNIITGSA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  106.12
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-O-cyclohexylidene-6,8-diaza-3,4-dihydroxy-2-hydroxymethyl-1-oxaspiro<4.4>nonan-7,9-dione 在 三氟乙酸 作用下， 反应 2.0h， 以98%的产率得到(-)-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-D-altrono-1,5-lactone 在 吡啶 、 N-morpholine oxide 、 sodium azide 、 四丙基高钌酸铵 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.84h， 生成 (2R,3R,4R,5R)-3,4-O-cyclohexylidene-6,8-diaza-3,4-dihydroxy-2-hydroxymethyl-1-oxaspiro<4.4>nonan-7,9-dione
  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.