(3R,5aR,9aS,10aS)-5a-(methoxycarbonyl)-7,8-dimethyl-5-oxo-3-phenyl-2,3,9,9a,10,10a-hexahydro-6H-oxazolo[3,2-b]isoquinoline | 602302-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (3R,5aR,9aS,10aS)-5a-(methoxycarbonyl)-7,8-dimethyl-5-oxo-3-phenyl-2,3,9,9a,10,10a-hexahydro-6H-oxazolo[3,2-b]isoquinoline
• 英文别名: methyl (3R,5aR,9aS,10aS)-7,8-dimethyl-5-oxo-3-phenyl-3,6,9,9a,10,10a-hexahydro-2H-[1,3]oxazolo[3,2-b]isoquinoline-5a-carboxylate
• CAS: 602302-19-2
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: UWEQGHKBHGCAHG-RYLXDESZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 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,5aR,9aS,10aS)-5a-(methoxycarbonyl)-7,8-dimethyl-5-oxo-3-phenyl-2,3,9,9a,10,10a-hexahydro-6H-oxazolo[3,2-b]isoquinoline 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到(4aR,8aS)-8a-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethyl-2,3,4,4a,5,8-hexahydro-1H-isoquinoline
  参考文献：
  名称：

  Diels–Alder reactions of phenylglycinol-derived bicyclic lactams. Enantiodivergent synthesis of cis-hydroisoquinolines

  摘要：

  The diastereomeric phenylglycino-derived unsaturated delta-lactams trans-3 and cis-3 react with dienes with exo facial diastereoselectivity to give the corresponding tricyclic adducts, which were ultimately converted to enantiomeric cis-hydroisoquinolines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00368-9
• 作为产物：
  描述：

  (3R,8aS)-6-(methoxycarbonyl)-5-oxo-3-phenyl-6-(phenylselanyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 在 臭氧 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (3R,5aR,9aS,10aS)-5a-(methoxycarbonyl)-7,8-dimethyl-5-oxo-3-phenyl-2,3,9,9a,10,10a-hexahydro-6H-oxazolo[3,2-b]isoquinoline
  参考文献：
  名称：

  Diels–Alder reactions of phenylglycinol-derived bicyclic lactams. Enantiodivergent synthesis of cis-hydroisoquinolines

  摘要：

  The diastereomeric phenylglycino-derived unsaturated delta-lactams trans-3 and cis-3 react with dienes with exo facial diastereoselectivity to give the corresponding tricyclic adducts, which were ultimately converted to enantiomeric cis-hydroisoquinolines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00368-9

文献信息

• Diels–Alder reactions of phenylglycinol-derived bicyclic lactams. Enantiodivergent synthesis of cis-hydroisoquinolines
  作者：Núria Casamitjana、Mercedes Amat、Núria Llor、Marçal Carreras、Xavier Pujol、M. Montserrat Fernández、Virgina López、Elies Molins、Carles Miravitlles、Joan Bosch

  DOI：10.1016/s0957-4166(03)00368-9

  日期：2003.7

  The diastereomeric phenylglycino-derived unsaturated delta-lactams trans-3 and cis-3 react with dienes with exo facial diastereoselectivity to give the corresponding tricyclic adducts, which were ultimately converted to enantiomeric cis-hydroisoquinolines. (C) 2003 Elsevier Science Ltd. All rights reserved.