2-(4-bromophenyl)-5-methyl-7,8-dihydro-6H-cyclopenta[g]pyrazolo[1,5-a]pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-bromophenyl)-5-methyl-7,8-dihydro-6H-cyclopenta[g]pyrazolo[1,5-a]pyrimidine
• 英文别名: 2-(4-bromophenyl)-5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1,5-a]pyrimidine；11-(4-bromophenyl)-7-methyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene
• 化学式: C₁₆H₁₄BrN₃
• 分子量: 328.211
• InChiKey: BLWVNWKKJGHBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基环戊酮 、 5-氨基-3-(4-溴苯基)-1H-吡唑 反应 0.03h， 以83%的产率得到2-(4-bromophenyl)-5-methyl-7,8-dihydro-6H-cyclopenta[g]pyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  5-氨基-1 H-吡唑与含五元环的β-二羰基化合物的反应选择性合成稠合的吡唑并[1,5- a ]嘧啶

  摘要：

  3-取代的5-氨基-1 H-吡唑与2-乙酰基环戊酮或2-乙氧基羰基-乙烯基环戊酮的反应以高收率形成了一系列新的环戊吡唑并[1,5- a ]嘧啶区域选择性形成。当使用2-乙酰基丁内酯，将反应提供6-（2-羟基乙基）吡唑并[1,5-一个]嘧啶酮和/或中间（3 Ž）-3- {1 - [（5- [R -1 ħ -吡唑-3-基）氨基]亚乙基} -4，5-二氢呋喃酮。这表明作为最后一步的丁内酯开环进行环化反应。考虑了该区域选择性反应的几个方面，包括机理和结构研究。

  DOI：

  10.1016/j.tet.2011.12.001

文献信息

• Hydrogen-bonded chains in isostructural 5-methyl-2-(4-methylphenyl)-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine, 2-(4-chlorophenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine and 2-(4-bromophenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine, and sheets of π-stacked hydrogen-bonded chains in 2-(4-methoxyphenyl)-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>g</i>]pyrazolo[1,5-<i>a</i>]pyrimidine
  作者：Jaime Portilla、Jairo Quiroga、Justo Cobo、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108270105016720

  日期：2005.7.15

  5-Methyl-2-(4-methylphenyl)-7,8-dihydro-6H-cyclopenta[ g]pyrazolo[ 1,5-a] pyrimidine, C17H17N3, 2-(4-chlorophenyl)-5-methyl- 7,8-dihydro-6H-cyclopenta[g] pyrazolo[1,5-a] pyrimidine, C16H14ClN3, and 2-(4-bromophenyl)-5-methyl-7,8-dihydro-6H- cyclopenta[g] pyrazolo[ 1,5- a] pyrimidine, C16H14BrN3, are isostructural; in each compound, the molecules are linked into chains by a single C - H center dot center dot center dot pi(arene) hydrogen bond. Molecules of 2-(4-methoxyphenyl)-5-methyl- 7,8-dihydro-6H-cyclopenta[ g] pyrazolo[ 1,5- a] pyrimidine, C17H17N3O, are linked by a single C - H center dot center dot center dot N hydrogen bond into chains, which are themselves linked into sheets by a pi-pi stacking interaction.
• 2-<i>tert</i>-Butyl-5-methyl-7,8-dihydro-6<i>H</i>-cyclopenta[<i>e</i>]pyrazolo[1,5-<i>a</i>]pyrimidine: molecular stacks built from C—H...π(pyrazole) hydrogen bonds and π–π stacking interactions
  作者：Jaime Portilla、Jairo Quiroga、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s010827010802266x

  日期：2008.9.15

  In the title compound, C14H19N3, the bond distances within the heterocyclic portion of the molecule indicate incomplete pi delocalization. The molecules are linked into stacks by a combination of two C-H center dot center dot center dot pi(pyrazole) hydrogen bonds and two independent pi-pi stacking interactions between inversion-related pyrimidine rings. The significance of this study lies in its observation of significant differences in both molecular conformation and supramolecular aggregation between the title compound, an example of a 2-alkylpyrazolo[1,5-a] pyrimidine, and some analogous 2-arylpyrazolo[1,5-a] pyrimidines.