2-(N-benzylcarbamoyl)-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-3-one | 1176260-21-1

• 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: 2-(N-benzylcarbamoyl)-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-3-one
• CAS: 1176260-21-1
• 化学式: C₂₃H₂₄N₂O₄
• 分子量: 392.455
• InChiKey: BVYGBNTYLQLISR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(N-benzylcarbamoyl)-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo[2,1-a]isoquinolin-3-one 、 苄胺 以 水 为溶剂， 以72%的产率得到(1SR,2SR,10bSR)-1-benzylamino-2-N-benzylcarbamoyl-10b-methyl-8,9-dimethoxy-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
• 作为产物：
  描述：

  2-benzyloxycarbonyl-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo-[2,1-a]isoquinolin-3-one 、 苄胺 以 水 为溶剂， 以60%的产率得到2-(N-benzylcarbamoyl)-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo[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

文献信息

• Stereocontrolled conjugate additions to dihydroindolizinone systems. Synthesis of enantiopure polysubstituted tetrahydropyrrolo[2,1-a]isoquinolones
  作者：Cristina Camarero、Inés González-Temprano、Asier Gómez-SanJuan、Sonia Arrasate、Esther Lete、Nuria Sotomayor

  DOI：10.1016/j.tet.2009.05.011

  日期：2009.7

  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.