N-(1,3-dimethyl-2,4-dioxopyrimidyl)methyl-1,2,3,4-tetrahydroisoquinoline | 145474-56-2

• 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: N-(1,3-dimethyl-2,4-dioxopyrimidyl)methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 145474-56-2
• 化学式: C₁₆H₁₉N₃O₂
• 分子量: 285.346
• InChiKey: WUNHDXZFVDCLAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1,3-dimethyl-2,4-dioxopyrimidyl)methyl-1,2,3,4-tetrahydroisoquinoline 在 silver carbonate 作用下， 以 xylene 为溶剂， 反应 43.0h， 以42%的产率得到5,6-dihydro(1,3-dimethyl-2,4-dioxo)pyrimido<5,6-a>benzoindolizine
  参考文献：
  名称：

  XYZH systems as potential 1,3-dipoles. Part 36. 1,5-Electrocyclisation processes via oxidation of tertiary amines. Pyrrolo-dihydroisoquinolines and -dihydro-β-carbolines.

  摘要：

  A range of tertiary N-allylamines derived from 1,2,3,4-tetrahydroisoquinoline undergo oxidative cyclisation, induced by Ag2CO3, to pyrrolo-dihydroisoquinolines in moderate to good yield. Analogous oxidative cyclisations are reported for N-allyl-tetrahydro-beta-carbolines and a pyrrolidine. The reactions proceed via formation of a 1,5-dipole followed by an electrocyclisation and subsequent aromatisation.

  DOI：

  10.1016/s0040-4020(01)81190-x
• 作为产物：
  描述：

  2-(2,4-dioxopyrimidyl)methyl-1,2,3,4-tetrahydroisoquinoline 、 碘甲烷 在 四乙基氟化铵水合物 作用下， 生成 N-(1,3-dimethyl-2,4-dioxopyrimidyl)methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  XYZH systems as potential 1,3-dipoles. Part 36. 1,5-Electrocyclisation processes via oxidation of tertiary amines. Pyrrolo-dihydroisoquinolines and -dihydro-β-carbolines.

  摘要：

  A range of tertiary N-allylamines derived from 1,2,3,4-tetrahydroisoquinoline undergo oxidative cyclisation, induced by Ag2CO3, to pyrrolo-dihydroisoquinolines in moderate to good yield. Analogous oxidative cyclisations are reported for N-allyl-tetrahydro-beta-carbolines and a pyrrolidine. The reactions proceed via formation of a 1,5-dipole followed by an electrocyclisation and subsequent aromatisation.

  DOI：

  10.1016/s0040-4020(01)81190-x

文献信息

• XYZH systems as potential 1,3-dipoles. Part 36. 1,5-Electrocyclisation processes via oxidation of tertiary amines. Pyrrolo-dihydroisoquinolines and -dihydro-β-carbolines.
  作者：Ronald Grigg、Peter Myers、Anoma Somasunderam、Visuvanathar Sridharan

  DOI：10.1016/s0040-4020(01)81190-x

  日期：1992.1

  A range of tertiary N-allylamines derived from 1,2,3,4-tetrahydroisoquinoline undergo oxidative cyclisation, induced by Ag2CO3, to pyrrolo-dihydroisoquinolines in moderate to good yield. Analogous oxidative cyclisations are reported for N-allyl-tetrahydro-beta-carbolines and a pyrrolidine. The reactions proceed via formation of a 1,5-dipole followed by an electrocyclisation and subsequent aromatisation.