N-(pyrazolo[1,5-a]pyridin-3-ylmethyl)piperazine | 511254-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: N-(pyrazolo[1,5-a]pyridin-3-ylmethyl)piperazine
• 英文别名: 3-(Piperazin-1-ylmethyl)pyrazolo[1,5-a]pyridine；3-(piperazin-1-ylmethyl)pyrazolo[1,5-a]pyridine
• CAS: 511254-90-3
• 化学式: C₁₂H₁₆N₄
• 分子量: 216.286
• InChiKey: HATKYQMFHSBGSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Rp)-trifluoromethanesulfonic acid (4-[2.2]paracyclophane) ester 、 N-(pyrazolo[1,5-a]pyridin-3-ylmethyl)piperazine 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (S)-3-(4-[2.2]paracyclophan-4-ylpiperazin-1-ylmethyl)pyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality

  摘要：

  employing yeast enzymes, natural amino acids and the Jacobsen's catalyst as sources of chirality, we have synthesized pyrazolo[1,5-a]pyridine derivatives with central- and planar-chirality as analogs of the dopamine D4 receptor ligand FAUC 113. In vitro binding experiments displayed enhanced D2 and D3 affinity for both enantiomers of the [2.2]paracyclophane 3. The C-methylpiperazine (R)-4a revealed excellent D4 selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00639-0
• 作为产物：
  描述：

  4-(pyrazolo[1,5-a]pyridin-3-ylmethyl)piperazinyl-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以90%的产率得到N-(pyrazolo[1,5-a]pyridin-3-ylmethyl)piperazine
  参考文献：
  名称：

  Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality

  摘要：

  employing yeast enzymes, natural amino acids and the Jacobsen's catalyst as sources of chirality, we have synthesized pyrazolo[1,5-a]pyridine derivatives with central- and planar-chirality as analogs of the dopamine D4 receptor ligand FAUC 113. In vitro binding experiments displayed enhanced D2 and D3 affinity for both enantiomers of the [2.2]paracyclophane 3. The C-methylpiperazine (R)-4a revealed excellent D4 selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00639-0

文献信息

• Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality
  作者：Stefan Löber、Birgit Ortner、Laura Bettinetti、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0957-4166(02)00639-0

  日期：2002.10

  employing yeast enzymes, natural amino acids and the Jacobsen's catalyst as sources of chirality, we have synthesized pyrazolo[1,5-a]pyridine derivatives with central- and planar-chirality as analogs of the dopamine D4 receptor ligand FAUC 113. In vitro binding experiments displayed enhanced D2 and D3 affinity for both enantiomers of the [2.2]paracyclophane 3. The C-methylpiperazine (R)-4a revealed excellent D4 selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.