(1R,10bR)-(+)-8,9-dimethoxy-1,10b-dimethyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3-one | 1176260-32-4

• 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: (1R,10bR)-(+)-8,9-dimethoxy-1,10b-dimethyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3-one
• 英文别名: (1R,10bR)-8,9-dimethoxy-1,10b-dimethyl-1,2,5,6-tetrahydropyrrolo[2,1-a]isoquinolin-3-one
• CAS: 1176260-32-4
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: AYBSXIVLPQGRAW-QLJPJBMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2R,10bR)-(+)-2-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-ylmethylsulfinyl)-8,9-dimethoxy-1,10b-dimethyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3-one 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 以56%的产率得到(1R,10bR)-(+)-8,9-dimethoxy-1,10b-dimethyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3-one
  参考文献：
  名称：

  Stereocontrolled conjugate additions to dihydroindolizinone systems. Synthesis of enantiopure polysubstituted tetrahydropyrrolo[2,1-a]isoquinolones

  摘要：

  Conjugate addition reactions of various types of nucleophiles to the gamma-lactam unit of dihydroindolizinone systems have been studied. The addition of cuprates, amines or stabilized carbanions requires the activation of the unsaturated bicyclic lactam with a EWG at C-2, while sulfur-stabilized carbanions are reactive enough to add to the unsubstituted lactam. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, and the incoming nucleophile. Thus 1,10b-cis or 1,10b-trans diastereomers could be obtained selectively with dr>95:5. The tandem conjugate addition-alkylation also takes place in good yields. These reactions have been applied to the synthesis of enantiopure tetrahydropyrrolo [2,1-a]isoquinolines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.011