2,5-trans-2',5'-trans-5,5'-dimethylperhydro-2,2'-bipyrimidine | 155052-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-trans-2',5'-trans-5,5'-dimethylperhydro-2,2'-bipyrimidine
• CAS: 155052-84-9
• 化学式: C₁₀H₂₂N₄
• 分子量: 198.311
• InChiKey: NHBWHIOGGRSAOZ-DFLMOOGLSA-N

物化性质

• 沸点：
  302.0±10.0 °C(predicted)
• 密度：
  0.941±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.12
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2,5-trans-2',5'-trans-5,5'-dimethylperhydro-2,2'-bipyrimidine 以 甲醇 、 水 为溶剂， 反应 1.0h， 以52%的产率得到(2R*,4aR*,4bR*,5R*)-2,7-dimethylperhydro-4,5,8a,9a-tetraazafluorene
  参考文献：
  名称：

  Synthesis and stereochemical assignment of 2,5-trans-2′,5′-trans-5,5′-dimethylperhydro-2,2′-bipyrimidine and heterocycles derived from its condensation with formaldehyde

  摘要：

  2-Methylpropane-1,3-diamine reacts with glyoxal to give 2,5-trans-2',5'-trans-5,5'-dimethylperhydro-2,2'-bipyrimidine 5. Subsequent treatment of 5 (i) with one equiv of HCHO gives a tricyclic product mixture from which (2R*,4aR*,4bR*,5R*)-2,7-dimethylperhydro-4,5,8a,9a-tetraazafluorene 6a is obtained crystalline, and (ii) with two equiv of HCHO gives a 1.5 : 1.0 mixture of (2R*,6S*,8bR*,8cR*)-dimethylperhydro-3a,4a,7a,8a-tetraazacyclopentano-[def]fluorene 11 and (2R*,6S*,8bR*,8cR*)-dimethylperhydro-3a,4a,7a,8a-tetraazacyclopentano[def]fluorene 12 from which 11 is obtained pure. The configurational assignment of 6a is made on the basis of molecular mechanics calculations and these lead to a revision of a previous conformational assignment of the parent tricycle 4a,4b-trans-perhydro-4a,5,8a,9a-tetraazafluorene 7 and of its 9-methyl derivative 9.

  DOI：

  10.1016/s0040-4020(01)86966-0
• 作为产物：
  描述：

  2-甲基-1,3-丙二胺 、 草酸醛 以 乙醇 、 水 为溶剂， 反应 3.5h， 以40%的产率得到2,5-trans-2',5'-trans-5,5'-dimethylperhydro-2,2'-bipyrimidine
  参考文献：
  名称：

  Synthesis and stereochemical assignment of 2,5-trans-2′,5′-trans-5,5′-dimethylperhydro-2,2′-bipyrimidine and heterocycles derived from its condensation with formaldehyde

  摘要：

  2-Methylpropane-1,3-diamine reacts with glyoxal to give 2,5-trans-2',5'-trans-5,5'-dimethylperhydro-2,2'-bipyrimidine 5. Subsequent treatment of 5 (i) with one equiv of HCHO gives a tricyclic product mixture from which (2R*,4aR*,4bR*,5R*)-2,7-dimethylperhydro-4,5,8a,9a-tetraazafluorene 6a is obtained crystalline, and (ii) with two equiv of HCHO gives a 1.5 : 1.0 mixture of (2R*,6S*,8bR*,8cR*)-dimethylperhydro-3a,4a,7a,8a-tetraazacyclopentano-[def]fluorene 11 and (2R*,6S*,8bR*,8cR*)-dimethylperhydro-3a,4a,7a,8a-tetraazacyclopentano[def]fluorene 12 from which 11 is obtained pure. The configurational assignment of 6a is made on the basis of molecular mechanics calculations and these lead to a revision of a previous conformational assignment of the parent tricycle 4a,4b-trans-perhydro-4a,5,8a,9a-tetraazafluorene 7 and of its 9-methyl derivative 9.

  DOI：

  10.1016/s0040-4020(01)86966-0