cis-4a-methyl-1,13a-dihydrobenzo[5,6][1,4]oxazino[4,3-b]isoquinoline-2,12(4aH,6H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: cis-4a-methyl-1,13a-dihydrobenzo[5,6][1,4]oxazino[4,3-b]isoquinoline-2,12(4aH,6H)-dione
• 英文别名: (4aS,13aR)-4a-methyl-6,13a-dihydro-1H-isoquinolino[3,2-c][1,4]benzoxazine-2,12-dione
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: ULHQBGKISNRAQM-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-4a-methyl-1,13a-dihydrobenzo[5,6][1,4]oxazino[4,3-b]isoquinoline-2,12(4aH,6H)-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 (4a,13a)-cis-7-bromo-4a-methyl-1,13a-dihydrobenzo[5,6][1,4]oxazino[4,3-b]isoquinoline-2,12(4aH,6H)-dione
  参考文献：
  名称：

  Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation

  摘要：

  Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an (c)-Michael addition process or hydrobenzofurans through a (N)Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of Cp*Rh-III-catalyzed C-H activation cascade reactions.

  DOI：

  10.1021/ja5072702
• 作为产物：
  描述：

  苯甲羟肟酸 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.5h， 生成 cis-4a-methyl-1,13a-dihydrobenzo[5,6][1,4]oxazino[4,3-b]isoquinoline-2,12(4aH,6H)-dione
  参考文献：
  名称：

  Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation

  摘要：

  Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an (c)-Michael addition process or hydrobenzofurans through a (N)Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of Cp*Rh-III-catalyzed C-H activation cascade reactions.

  DOI：

  10.1021/ja5072702