(3S,8aR)-8a-methyl-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one | 170710-79-9

• 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: (3S,8aR)-8a-methyl-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 170710-79-9
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: LXOGYWPPBRDCIO-TZMCWYRMSA-N

物化性质

• 沸点：
  388.3±31.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,8aR)-8a-methyl-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 三氯化铝 、 氢气 作用下， 生成 (S)-(+)-2-甲基哌啶
  参考文献：
  名称：

  New highly enantioselective synthesis of 6-alkylpiperidin-2-ones and 2-substituted piperidines

  摘要：

  A versatile and highly enantioselective approach to 2-substituted piperidines is described using phenylglycinol as chiral auxiliary.

  DOI：

  10.1016/0957-4166(95)00348-s
• 作为产物：
  描述：

  L-苯甘氨醇 、 5-氧代己酸 以 甲苯 为溶剂， 生成 (3S,8aS)-8a-Methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 、 (3S,8aR)-8a-methyl-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one
  参考文献：
  名称：

  New highly enantioselective synthesis of 6-alkylpiperidin-2-ones and 2-substituted piperidines

  摘要：

  A versatile and highly enantioselective approach to 2-substituted piperidines is described using phenylglycinol as chiral auxiliary.

  DOI：

  10.1016/0957-4166(95)00348-s

文献信息

• An Asymmetric Approach to Spirocylic Systems:  A Formal Synthesis of Zizaene
  作者：Robert C. Hughes、Curt A. Dvorak、A. I. Meyers

  DOI：10.1021/jo010439p

  日期：2001.8.1

  A general route to enantiopure spirocarbocycles is described. The use of various chiral bicyclic lactams 1 that have been doubly alkylated with olefinic halides gives good yields of alpha,alpha -disubstituted chiral lactams 2 which were cyclized to spiro-olefins using ring closure metathesis methodology (Grubbs' catalyst). These spirolactams 3, formed in generally excellent yields, were shown to be smoothly transformed into spirocyclopentenone 6, spirocyclohexenone, 7, and spirolactams 8. Further demonstration of this spirocyclization methodology was featured in a formal synthesis of zizaene, by preparing in enantiomeric form the Coates' intermediate 21. This synthetic effort provided additional examples of the synthetic versatility of chiral bicyclic lactams 2a,b.
• New highly enantioselective synthesis of 6-alkylpiperidin-2-ones and 2-substituted piperidines
  作者：Stéphanie Fréville、Jean Pierre Célérier、Vu Moc Thuy、Gérard Lhommet

  DOI：10.1016/0957-4166(95)00348-s

  日期：1995.11

  A versatile and highly enantioselective approach to 2-substituted piperidines is described using phenylglycinol as chiral auxiliary.
• An Asymmetric Route to Chiral, Nonracemic 2-Substituted Piperidines. Synthesis of (-)-Pipecoline, (+)-Coniine, and (-)-Coniceine
  作者：Michael J. Munchhof、A. I. Meyers

  DOI：10.1021/jo00127a005

  日期：1995.11