tert-Butyl 1-(2-(dimethylamino)-1-methoxy-4-oxo-3-phenyl-2-cyclobuten-1-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate

• 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: tert-Butyl 1-(2-(dimethylamino)-1-methoxy-4-oxo-3-phenyl-2-cyclobuten-1-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate
• 英文别名: tert-butyl 1-[2-(dimethylamino)-1-methoxy-4-oxo-3-phenylcyclobut-2-en-1-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• 化学式: C₂₇H₃₂N₂O₄
• 分子量: 448.562
• InChiKey: CFCIJWHBXHLKOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl 1-(2-(dimethylamino)-1-methoxy-4-oxo-3-phenyl-2-cyclobuten-1-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-Dimethylamino-4-methoxy-2-phenyl-4-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-cyclobut-2-enone
  参考文献：
  名称：

  Cyclobutenedione-Based Method for the Synthesis of Substituted 2-Pyridinones and Dihydro-2-pyridinones

  摘要：

  1,2-Addition of N-Boc-protected alpha-amino carbanions to cyclobutenediones followed by methylation of the resulting alkoxides generated 4-(1-N-Boc-aminoalkyl)-4-methoxy-3-cyclobutenones. Removal of the Boc protecting group and thermal ring expansion gave dihydro-2-pyridinones in good yields. Treatment of the dihydro-2-pyridinones with NBS/pyridine led to the formation of the corresponding 2-pyridinones. This methodology proved general with regard to both the cyclobutenediones and alpha-amino carbanions.

  DOI：

  10.1021/jo990069t
• 作为产物：
  描述：

  3-N,N-dimethylamino-4-phenyl-3-cyclobutene-1,2-dione 、 tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate 、 三氟甲烷磺酸甲酯 生成 tert-Butyl 1-(2-(dimethylamino)-1-methoxy-4-oxo-3-phenyl-2-cyclobuten-1-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate
  参考文献：
  名称：

  Cyclobutenedione-Based Method for the Synthesis of Substituted 2-Pyridinones and Dihydro-2-pyridinones

  摘要：

  1,2-Addition of N-Boc-protected alpha-amino carbanions to cyclobutenediones followed by methylation of the resulting alkoxides generated 4-(1-N-Boc-aminoalkyl)-4-methoxy-3-cyclobutenones. Removal of the Boc protecting group and thermal ring expansion gave dihydro-2-pyridinones in good yields. Treatment of the dihydro-2-pyridinones with NBS/pyridine led to the formation of the corresponding 2-pyridinones. This methodology proved general with regard to both the cyclobutenediones and alpha-amino carbanions.

  DOI：

  10.1021/jo990069t