(4aR,8aR)-7-Oxo-4a-(pyrrolidine-1-carbonyl)-3,4,4a,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid ethyl ester | 143957-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4aR,8aR)-7-Oxo-4a-(pyrrolidine-1-carbonyl)-3,4,4a,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid ethyl ester
• 英文别名: ethyl (4aR,8aR)-7-oxo-4a-(pyrrolidine-1-carbonyl)-3,4,8,8a-tetrahydro-1H-isoquinoline-2-carboxylate
• CAS: 143957-56-6
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: QQVBCEZPYUOZGR-GUYCJALGSA-N

物化性质

• 沸点：
  509.4±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  {2-[4-Oxo-1-(pyrrolidine-1-carbonyl)-cyclohexa-2,5-dienyl]-ethyl}-trimethylsilanylmethyl-carbamic acid ethyl ester 在 9,10-二氰基蒽 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以20%的产率得到(4aR,8aR)-7-Oxo-4a-(pyrrolidine-1-carbonyl)-3,4,4a,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Exploratory studies of .alpha.-silylamino- and .alpha.-silylamido-2,5-cyclohexadien-1-one SET photochemistry. Methodology for synthesis of functionalized hydroisoquinolines

  摘要：

  The electron-transfer (SET) photochemistry of selected alpha-silylamino and alpha-silylamido 2,5-cyclohexadienones has been explored with the intent of developing a novel and potentially efficient method for functionalized hydroisoquinoline synthesis. These substances, prepared by Birch reduction-alkylation-oxidation sequences, were found to undergo 9,10-dicyanoanthracene-SET-sensitized radical cyclization to form hydroisoquinolines in a highly regio- and stereoselective fashion and in modest to good yields. In contrast, the major direct irradiation reaction pathway followed by the alpha-silylamido-substituted systems involves type A rearrangement to bicyclic cyclohexenones or phenols. Direct irradiation of the alpha-silylamino analogs, on the other hand, brings about near-exclusive conversion to the corresponding hydroisoquinolines. The synthetic and mechanistic features of this study are described.

  DOI：

  10.1021/jo00048a046