7-butyl-9-(hexahydro-2,5-methanopentalene-3a-carboxamido)-6,8-dioxo-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,6-a]pyrimidine | 524944-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 7-butyl-9-(hexahydro-2,5-methanopentalene-3a-carboxamido)-6,8-dioxo-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,6-a]pyrimidine
• 英文别名: N-(7-butyl-6,8-dioxo-1,2,3,4-tetrahydropyrimido[1,2-c]pyrimidin-9-yl)tricyclo[3.3.1.03,7]nonane-3-carboxamide
• CAS: 524944-80-7
• 化学式: C₂₁H₃₀N₄O₃
• 分子量: 386.494
• InChiKey: HOSIGFFVBZHXRU-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-butyl-9-(hexahydro-2,5-methanopentalene-3a-carboxamido)-6,8-dioxo-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,6-a]pyrimidine 在 六甲基二硅氮烷 作用下， 反应 18.0h， 以63%的产率得到9-butyl-2-(hexahydro-2,5-methanopentalen-3a-yl)-4,5-dihydro-6H,8H-pyrimido[1,2,3-cd]purine-8,10(9H)-dione
  参考文献：
  名称：

  Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones

  摘要：

  The alkylation of 3-substituted cycloalkylcarboxamido-6-aminouraciI derivatives with 3-bromo-1-propanol followed by ring closure yields 1,3,8-trisubstituted xanthine derivatives bearing a polar hydroxyl group. Use of the more reactive 1,3-dibromopropane or homologous dibromoalkanes for the alkylation reaction results in simultaneous alkylation at N1 and the exocyclic amino group (N-6) yielding imidazo-, pyrimido- and diazepino-pyrimidine derivatives. The pyrimidopyrimidine derivatives can subsequently be cyclised using hexamethyldisilazane at high temperature affording an easy, convenient and general access to tricyclic pyrimido[1,2,3-cd]purinediones. Alternatively, 3-substituted 6-amino-5-benzylideneaminouraciI derivatives can be reacted with 1,3-dibromopropane followed by an oxidative cyclisation using thionyl chloride to obtain the desired tricyclic pyrimido[1,2,3-cd]purinediones, which are sterically fixed analogues of pharmacologically active purine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01485-0
• 作为产物：
  描述：

  3-甲基碳酸胺 在 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 7-butyl-9-(hexahydro-2,5-methanopentalene-3a-carboxamido)-6,8-dioxo-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,6-a]pyrimidine
  参考文献：
  名称：

  Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones

  摘要：

  The alkylation of 3-substituted cycloalkylcarboxamido-6-aminouraciI derivatives with 3-bromo-1-propanol followed by ring closure yields 1,3,8-trisubstituted xanthine derivatives bearing a polar hydroxyl group. Use of the more reactive 1,3-dibromopropane or homologous dibromoalkanes for the alkylation reaction results in simultaneous alkylation at N1 and the exocyclic amino group (N-6) yielding imidazo-, pyrimido- and diazepino-pyrimidine derivatives. The pyrimidopyrimidine derivatives can subsequently be cyclised using hexamethyldisilazane at high temperature affording an easy, convenient and general access to tricyclic pyrimido[1,2,3-cd]purinediones. Alternatively, 3-substituted 6-amino-5-benzylideneaminouraciI derivatives can be reacted with 1,3-dibromopropane followed by an oxidative cyclisation using thionyl chloride to obtain the desired tricyclic pyrimido[1,2,3-cd]purinediones, which are sterically fixed analogues of pharmacologically active purine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01485-0

文献信息

• Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones
  作者：Stefanie Weyler、Alaa M Hayallah、Christa E Müller

  DOI：10.1016/s0040-4020(02)01485-0

  日期：2003.1

  The alkylation of 3-substituted cycloalkylcarboxamido-6-aminouraciI derivatives with 3-bromo-1-propanol followed by ring closure yields 1,3,8-trisubstituted xanthine derivatives bearing a polar hydroxyl group. Use of the more reactive 1,3-dibromopropane or homologous dibromoalkanes for the alkylation reaction results in simultaneous alkylation at N1 and the exocyclic amino group (N-6) yielding imidazo-, pyrimido- and diazepino-pyrimidine derivatives. The pyrimidopyrimidine derivatives can subsequently be cyclised using hexamethyldisilazane at high temperature affording an easy, convenient and general access to tricyclic pyrimido[1,2,3-cd]purinediones. Alternatively, 3-substituted 6-amino-5-benzylideneaminouraciI derivatives can be reacted with 1,3-dibromopropane followed by an oxidative cyclisation using thionyl chloride to obtain the desired tricyclic pyrimido[1,2,3-cd]purinediones, which are sterically fixed analogues of pharmacologically active purine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.