(3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline | 864967-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline
• 英文别名: methyl (3R,6aR,10aS,10bR)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-[1,3]oxazolo[2,3-a]isoquinoline-6-carboxylate
• CAS: 864967-37-3
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: DQEPQPVBRKUZDH-YOTVNTGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline 在 lithium aluminium tetrahydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 (2R)-2-[(4R,4aR,8aS)-4-[2-(1,3-dioxolan-2-yl)ethyl]-4-(hydroxymethyl)-1,3,4a,5,8,8a-hexahydroisoquinolin-2-yl]-2-phenylethanol
  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：

  (3R,8R,8aR)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-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 (3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline
  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

• First enantioselective synthesis of tetracyclic intermediates en route to madangamine D
  作者：Mercedes Amat、Roberto Ballette、Stefano Proto、Maria Pérez、Joan Bosch

  DOI：10.1039/c3cc41104d

  日期：——

  The enantioselective synthesis of advanced tetracyclic precursors of madangamine D, bearing rings ABCD of this alkaloid, is reported. The saturated 14-membered ring is assembled from functionalized diazatricyclic intermediates following either ring-closing metathesis or macrolactamization strategies.

  据报道，带有该生物碱的ABCD环的madangamine D的高级四环前体的对映选择性合成。遵循闭环复分解或大内酰胺化策略，由官能化的二氮三环中间体组装而成的饱和14元环。