(3R,8S,8aS)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine | 917977-23-2

• 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: (3R,8S,8aS)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• 英文别名: (3R,8S,8aS)-3-phenyl-8-prop-2-enyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 917977-23-2
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: PMYGJYVSRFHLDF-YCPHGPKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (3R,8S,8aS)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (5S,6R)-5,6-diallyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-piperidone 、 (5S,6S)-5,6-diallyl-1-[(1R)-2-hydroxy-1-phenylethyl]-2-piperidone
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones

  摘要：

  Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic delta-oxoester 1a, two-step sequences involving a stereciselective alpha-amidoalkylation reaction, either with inversion or retention Of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.007
• 作为产物：
  描述：

  (3R,8R,8aR)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以73%的产率得到(3R,8S,8aS)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones

  摘要：

  Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic delta-oxoester 1a, two-step sequences involving a stereciselective alpha-amidoalkylation reaction, either with inversion or retention Of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.007

文献信息

• Dynamic Kinetic Resolution and Desymmetrization Processes: A Straightforward Methodology for the Enantioselective Synthesis of Piperidines
  作者：Mercedes Amat、Oriol Bassas、Núria Llor、Margalida Cantó、Maria Pérez、Elies Molins、Joan Bosch

  DOI：10.1002/chem.200600420

  日期：2006.10.16

  A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)-phenylglycinol or other amino alcohols

  报道了合成对映纯多取代哌啶的简单方法。它涉及直接产生已经在杂环上掺入碳取代基的手性非外消旋恶唑并[3，2-a]哌啶酮内酰胺，随后除去手性助剂。关键步骤是（R）-苯基甘醇或其他氨基醇与外消旋或手性δ-氧代（二）酸衍生物在高度立体选择性的过程中进行的环缩合反应，该过程涉及动态动力学拆分和/或非对映体或对映体酯基的去对称化。
• A general synthetic route to enantiopure cis-fused perhydrocycloalka[c]pyridines from phenylglycinol-derived lactams
  作者：Mercedes Amat、Maria Pérez、Annamaria T. Minaglia、Bruno Peretto、Joan Bosch

  DOI：10.1016/j.tet.2007.01.072

  日期：2007.6

  A synthetic route to enantiopure piperidines bearing a five-, six-, or seven-membered carbocyclic ring cis-fused on the c side of the heterocycle from a common phenylglycinol-derived δ-lactam is reported. Key steps are (i) a cyclocondensation reaction of (R)-phenylglycinol with a racemic γ-oxoester in a process that involves a dynamic kinetic resolution; (ii) a highly stereoselective conjugate addition

  据报道，从普通的苯甘醇衍生的δ-内酰胺到杂环的c端带有5、6或7元碳环顺式稠合的对映纯哌啶的合成路线已被报道。关键步骤是（i）（R）-苯基甘氨醇与外消旋γ-氧代酸酯的环缩合反应，该过程涉及动态动力学拆分；（ii）将有机铜酸酯高度立体选择性地共轭加成到不饱和δ-内酰胺上；（iii）闭环烯烃复分解。
• An Enantioselective Entry to <i>cis</i>-Perhydroisoquinolines
  作者：Mercedes Amat、Maria Pérez、Annamaria T. Minaglia、Núria Casamitjana、Joan Bosch

  DOI：10.1021/ol051242c

  日期：2005.8.1

  [GRAPHICS]An enantioselective route to cis-perhydroisoquinolines, involving a cycloconclensation reaction of (R)-phenylglycinol with a racemic oxoester, a stereoselective conjugate addition to an unsaturated bicyclic lactam, and the closure of the carbocyclic ring by a ring-closing metathesis as the key steps is reported. This route allows the preparation of 3-cyano derivatives as well as cis-octahydroisoquinolines bearing a quaternary center at the N-position.
• Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones
  作者：Mercedes Amat、Maria Pérez、Annamaria T. Minaglia、Daniele Passarella、Joan Bosch

  DOI：10.1016/j.tetasy.2008.10.007

  日期：2008.10

  Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic delta-oxoester 1a, two-step sequences involving a stereciselective alpha-amidoalkylation reaction, either with inversion or retention Of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones. (C) 2008 Elsevier Ltd. All rights reserved.