(1S,2R,10bS)-1,2-Bis<oxy>-1,2,3,5,6,10b-hexahydropyrrolo<2,1-a>isoquinolin-3-one | 172162-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1S,2R,10bS)-1,2-Bis<oxy>-1,2,3,5,6,10b-hexahydropyrrolo<2,1-a>isoquinolin-3-one
• 英文别名: (1S,2R,10bS)-1,2-bis(phenoxycarbothioyloxy)-2,5,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-3-one
• CAS: 172162-63-9
• 化学式: C₂₆H₂₁NO₅S₂
• 分子量: 491.588
• InChiKey: QHZLQRQBZFFTSB-RJGXRXQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R,10bS)-1,2-Bis<oxy>-1,2,3,5,6,10b-hexahydropyrrolo<2,1-a>isoquinolin-3-one 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (+)-(10bR)-1,2,3,5,6,10b-Hexahydropyrrolo-<2,1-a>isoquinoline
  参考文献：
  名称：

  Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid

  摘要：

  The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10. The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.

  DOI：

  10.1021/jo00127a019
• 作为产物：
  描述：

  (1S,2R,10bS)-1,2-dihydroxy-1,2,3,5,6,10bβ-hexahydropyrrolo<2,1-a>isoquinolin-3(2H)-one 、 硫代氯甲酸苯酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以41%的产率得到(1S,2R,10bS)-1,2-Bis<oxy>-1,2,3,5,6,10b-hexahydropyrrolo<2,1-a>isoquinolin-3-one
  参考文献：
  名称：

  Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid

  摘要：

  The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10. The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.

  DOI：

  10.1021/jo00127a019

文献信息

• Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid
  作者：Yong Sup Lee、Dong Wook Kang、Sook Ja Lee、Hokoon Park

  DOI：10.1021/jo00127a019

  日期：1995.11

  The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10. The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.