2-benzyloxycarbonyl-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo-[2,1-a]isoquinolin-3-one | 943766-88-9

• 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: 2-benzyloxycarbonyl-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo-[2,1-a]isoquinolin-3-one
• 英文别名: Benzyl 8,9-dimethoxy-10b-methyl-3-oxo-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylate；benzyl 8,9-dimethoxy-10b-methyl-3-oxo-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylate
• CAS: 943766-88-9
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: ZUEQIXBNGJENCE-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C(Solvent: Diethyl ether)
• 沸点：
  585.2±50.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-benzyloxycarbonyl-8,9-dimethoxy-10b-methyl-5,6-dihydropyrrolo-[2,1-a]isoquinolin-3-one 、 lithium hexamethyldisilazane 在 ammonium hydroxide 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以71%的产率得到(1RS,2RS)-2-benzylcarbonyl-1-(1,1,1,3,3,3-hexamethyldisilazan-2-yl)-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：

  在 吡啶 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 以479 mg的产率得到2-benzyloxycarbonyl-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

• Stereoselective Conjugate Additions to γ-Lactams: Synthesis of Polysubstituted Benzo-Fused Indolizidine Systems
  作者：Esther Lete、Cristina Camarero、Inés González-Temprano、Nuria Sotomayor

  DOI：10.1055/s-2007-973904

  日期：2007.4

  The stereoselectivity of the conjugate addition of carbon nucleophiles to the bicyclic γ-lactam unit of dihydropyrrolo[2,1- a]isoquinolones depends on the nature of the nucleophile and the substituent at the angular position.

  碳亲核试剂与二氢吡咯并[2,1-a]异喹诺酮类双环γ-内酰胺单元共轭加成的立体选择性取决于亲核试剂的性质和角位置的取代基。
• Camarero, Cristina; Arrasate, Sonia; Sotomayor, Nuria, ARKIVOC, 2010, vol. 2010, # 3, p. 45 - 55
  作者：Camarero, Cristina、Arrasate, Sonia、Sotomayor, Nuria、Lete, Esther

  DOI：——

  日期：——
• 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.