Acetic acid (3aS,7aS)-1-benzyl-4-methoxy-6-oxo-1,2,3,6,7,7a-hexahydro-indol-3a-ylmethyl ester | 143925-78-4

• 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: Acetic acid (3aS,7aS)-1-benzyl-4-methoxy-6-oxo-1,2,3,6,7,7a-hexahydro-indol-3a-ylmethyl ester
• CAS: 143925-78-4
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: LPFJJNZHWOLYBX-PKOBYXMFSA-N

反应信息

• 作为产物：
  描述：

  Acetic acid 1-[2-(benzyl-trimethylsilanylmethyl-amino)-ethyl]-2-methoxy-4-oxo-cyclohexa-2,5-dienylmethyl ester 在 9,10-二氰基蒽 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以25%的产率得到Acetic acid (4aS,8aS)-2-benzyl-5-methoxy-7-oxo-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-4a-ylmethyl 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