(4aR,8aS)-2-Benzyl-5-methoxy-3,7-dioxo-1,3,4,7,8,8a-hexahydro-2H-isoquinoline-4a-carboxylic acid methyl ester | 143925-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4aR,8aS)-2-Benzyl-5-methoxy-3,7-dioxo-1,3,4,7,8,8a-hexahydro-2H-isoquinoline-4a-carboxylic acid methyl ester
• CAS: 143925-74-0
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: RRBBYNOJNFCVEZ-AUUYWEPGSA-N

反应信息

• 作为产物：
  描述：

  1-[(Benzyl-trimethylsilanylmethyl-carbamoyl)-methyl]-2-methoxy-4-oxo-cyclohexa-2,5-dienecarboxylic acid methyl ester 在 9,10-二氰基蒽 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以2%的产率得到(4aR,8aS)-2-Benzyl-5-methoxy-3,7-dioxo-1,3,4,7,8,8a-hexahydro-2H-isoquinoline-4a-carboxylic acid methyl 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