(3R,8S,8aR)-8-allyl-6-methoxycarbonyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine | 864967-52-2

• 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,8aR)-8-allyl-6-methoxycarbonyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine
• 英文别名: methyl (3R,8S,8aR)-5-oxo-3-phenyl-8-prop-2-enyl-2,3,8,8a-tetrahydro-[1,3]oxazolo[3,2-a]pyridine-6-carboxylate
• CAS: 864967-52-2
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: HBMYTDXJACPJCF-JLJPHGGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,8S,8aR)-8-allyl-6-methoxycarbonyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) copper(l) iodide 、 三甲基氯硅烷 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (3R,6R,6aR,10aS,10bR)-6-ethyl-5-oxo-3-phenyl-3,6a,7,10,10a,10b-hexahydro-2H-[1,3]oxazolo[2,3-a]isoquinoline-6-carboxylate
  参考文献：
  名称：

  An Enantioselective Entry to cis-Perhydroisoquinolines

  摘要：

  [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.

  DOI：

  10.1021/ol051242c
• 作为产物：
  描述：

  D-苯甘氨醇 在 sodium sulfate 、 lithium hexamethyldisilazane 作用下， 以 乙醚 为溶剂， 75.0 ℃ 、2.0 kPa 条件下， 生成 (3R,8S,8aR)-8-allyl-6-methoxycarbonyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine
  参考文献：
  名称：

  An Enantioselective Entry to cis-Perhydroisoquinolines

  摘要：

  [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.

  DOI：

  10.1021/ol051242c

文献信息

• 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.