(3R,8aS)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine | 374890-37-6

• 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,8aS)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine
• 英文别名: (3R,8aS)-3-phenyl-2,3,8,8a-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 374890-37-6
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: BMGFHUOBWVAMOH-AAEUAGOBSA-N

物化性质

• 熔点：
  121-122 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  432.7±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,8aS)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以87%的产率得到(3R,6S,7S,8aS)-6,7-Dihydroxy-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-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：

  (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 在 potassium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.5h， 生成 (3R,8aS)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine
  参考文献：
  名称：

  与苯二酚衍生的不饱和δ-内酰胺的共轭加成。对映选择性合成油酸生物碱

  摘要：

  共轭加成的各种稳定的亲核试剂（2-吲哚烯醇化物和硫的稳定的阴离子）与苯基甘氨醇衍生的不饱和内酰胺的的立体化学结果反式- 2，顺式- 2，和它的8-乙基-取代的类似物10进行了研究。讨论了控制外向或内向面部立体选择性的因素。这种方法提供了合成顺式或反式的短途路线-3,4-二取代的对映体纯净的哌啶，以及在正常和20-epi系列中油酸碱生物碱的四环系统的对映选择性构建的有效途径。据报道该组几种生物碱的正式全合成。

  DOI：

  10.1021/jo0487101

文献信息

• Unsaturated oxazolopiperidone lactams: an unexpected domino-type double conjugate addition–cyclization process
  作者：Mercedes Amat、Núria Llor、Begoña Checa、Maria Pérez、Joan Bosch

  DOI：10.3998/ark.5550190.0015.202

  日期：——

  Reactions of 2-acetylindole enolate with unsaturate d oxazolopiperidones 3, 4 and 10 unexpectedly gives pentacyclic dilactams 6, 7 and 11 , respectively, resulting from a domino-type process involving two successive conjugate addition s and a final cyclization.

  2-乙酰吲哚烯醇化物与不饱和的 d 恶唑哌啶酮 3、4 和 10 的反应出人意料地分别产生了五环双内酰胺 6、7 和 11，这是由涉及两个连续共轭加成和最终环化的多米诺型过程产生的。
• Enantioselective formal synthesis of uleine alkaloids from phenylglycinol-derived bicyclic lactams
  作者：Mercedes Amat、Maria Pérez、Núria Llor、Marisa Martinelli、Elies Molins、Joan Bosch

  DOI：10.1039/b400987h

  日期：——

  two-step route for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, involving the stereoselective conjugate addition of an appropriate indole-containing nucleophile to a chiral bicyclic delta-lactam and the subsequent cyclization on the indole 3-position of the resulting 4,5-disubstituted 2-piperidone, has culminated in the formal total synthesis of several alkaloids

  乌兰碱生物碱的四环系统对映选择性构建的两步路线，包括将适当的含吲哚的亲核体立体选择性共轭加成到手性双环δ-内酰胺上，随后在所得吲哚的3-位环化4,5-二取代的2-哌啶酮最终达到了该组几种生物碱的正式全合成。
• Stereodivergent Synthesis of Enantiopure <i>cis</i>- and <i>trans</i>-3-Ethyl-4-piperidineacetates
  作者：Mercedes Amat、Maria Pérez、Núria Llor、Joan Bosch

  DOI：10.1021/ol0263245

  日期：2002.8.1

  [GRAPHICS]Starting from a common chiral bicyclic lactam 11, enantiopure trans- or cis-3-ethyl-4-piperidineacetate derivatives are obtained by conjugate addition of an enolate or a cuprate to the unsaturated lactams 12 or 18, respectively.
• Conjugate Additions to Phenylglycinol-Derived Unsaturated δ-Lactams. Enantioselective Synthesis of Uleine Alkaloids
  作者：Mercedes Amat、Maria Pérez、Núria Llor、Carmen Escolano、F. Javier Luque、Elies Molins、Joan Bosch

  DOI：10.1021/jo0487101

  日期：2004.12.1

  sulfur-stabilized anions) to the phenylglycinol-derived unsaturated lactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial stereoselectivity are discussed. This methodology provides short synthetic routes to either cis- or trans-3,4-disubstituted enantiopure piperidines as well as efficient routes for the enantioselective construction of the tetracyclic

  共轭加成的各种稳定的亲核试剂（2-吲哚烯醇化物和硫的稳定的阴离子）与苯基甘氨醇衍生的不饱和内酰胺的的立体化学结果反式- 2，顺式- 2，和它的8-乙基-取代的类似物10进行了研究。讨论了控制外向或内向面部立体选择性的因素。这种方法提供了合成顺式或反式的短途路线-3,4-二取代的对映体纯净的哌啶，以及在正常和20-epi系列中油酸碱生物碱的四环系统的对映选择性构建的有效途径。据报道该组几种生物碱的正式全合成。
• 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.