(3aS,5R,7aS,8S,8aS)-8-Hydroxy-2,2-dimethyl-5-phenyl-hexahydro-1,3,7-trioxa-4a-aza-s-indacen-4-one | 374890-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aS,5R,7aS,8S,8aS)-8-Hydroxy-2,2-dimethyl-5-phenyl-hexahydro-1,3,7-trioxa-4a-aza-s-indacen-4-one
• 英文别名: (3S,7S,8S,9S,12R)-8-hydroxy-5,5-dimethyl-12-phenyl-4,6,10-trioxa-1-azatricyclo[7.3.0.03,7]dodecan-2-one
• CAS: 374890-35-4
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: FQMYGGLPZSQKFT-CXOVXGEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,5R,7aS,8S,8aS)-8-Hydroxy-2,2-dimethyl-5-phenyl-hexahydro-1,3,7-trioxa-4a-aza-s-indacen-4-one 在 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (3R,4S,5R)-5-hydroxy-3,4-O-(1-methylethylidene)piperidine
  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：

  (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

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.