methyl (3R,6R,6aR,10aS,10bR)-6-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-5-oxo-3-phenyl-3,6a,7,10,10a,10b-hexahydro-2H-[1,3]oxazolo[2,3-a]isoquinoline-6-carboxylate | 864967-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl (3R,6R,6aR,10aS,10bR)-6-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-5-oxo-3-phenyl-3,6a,7,10,10a,10b-hexahydro-2H-[1,3]oxazolo[2,3-a]isoquinoline-6-carboxylate
• CAS: 864967-47-5
• 化学式: C₂₈H₄₁NO₅Si
• 分子量: 499.723
• InChiKey: WWKXUKQOEQNHPF-DGIOIMRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3R,6R,6aR,10aS,10bR)-6-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-5-oxo-3-phenyl-3,6a,7,10,10a,10b-hexahydro-2H-[1,3]oxazolo[2,3-a]isoquinoline-6-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 以79%的产率得到3-[(4R,4aR,8aS)-4-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-1,3,4a,5,8,8a-hexahydroisoquinolin-4-yl]propan-1-ol
  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：

  methyl 4-formyl-6-heptenoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) copper(l) iodide 、 三甲基氯硅烷 、 sodium sulfate 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 75.0 ℃ 、2.0 kPa 条件下， 反应 2.0h， 生成 methyl (3R,6R,6aR,10aS,10bR)-6-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-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