(3R,8S,8aS)-8-Hydroxy-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one | 374890-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,8S,8aS)-8-Hydroxy-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one
• 英文别名: (3R,8S,8aS)-8-hydroxy-3-phenyl-2,3,8,8a-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 374890-26-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: XJIOKOIHEGWRRE-GVXVVHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,8S,8aS)-8-Hydroxy-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one 在 四氧化锇 、 N-甲基吲哚酮 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (3aS,5R,7aS,8S,8aS)-8-Hydroxy-2,2-dimethyl-5-phenyl-hexahydro-1,3,7-trioxa-4a-aza-s-indacen-4-one
  参考文献：
  名称：

  Unprecedented Oxidation of a Phenylglycinol-Derived 2-Pyridone:  Enantioselective Synthesis of Polyhydroxypiperidines

  摘要：

  [GRAPHICS]The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective synthesis of (S)-N-Boc-3-hydroxypiperidine and (3R,4S)-3,4-dihydroxyplperidlne is also reported.

  DOI：

  10.1021/ol016418z
• 作为产物：
  描述：

  (1'R)-(-)-1-(2'-hydroxy-1'-phenyl-ethyl)-(1H)-pyridin-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (3R,8S,8aS)-8-Hydroxy-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one 、 (1aS,2S,4R,6aS,6bS)-2-Hydroxy-4-phenyl-hexahydro-1,6-dioxa-3a-aza-cyclopropa[e]inden-3-one 、 (1aS,2S,2aS,5R,6aS)-2-Hydroxy-5-phenyl-hexahydro-1,3-dioxa-5a-aza-cyclopropa[f]inden-6-one
  参考文献：
  名称：

  Unprecedented Oxidation of a Phenylglycinol-Derived 2-Pyridone:  Enantioselective Synthesis of Polyhydroxypiperidines

  摘要：

  [GRAPHICS]The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective synthesis of (S)-N-Boc-3-hydroxypiperidine and (3R,4S)-3,4-dihydroxyplperidlne is also reported.

  DOI：

  10.1021/ol016418z

文献信息

• Unprecedented Oxidation of a Phenylglycinol-Derived 2-Pyridone:  Enantioselective Synthesis of Polyhydroxypiperidines
  作者：Mercedes Amat、Núria Llor、Marta Huguet、Elies Molins、Enrique Espinosa、Joan Bosch

  DOI：10.1021/ol016418z

  日期：2001.10.1

  [GRAPHICS]The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective synthesis of (S)-N-Boc-3-hydroxypiperidine and (3R,4S)-3,4-dihydroxyplperidlne is also reported.