1-(Benzyloxy)-5-bromopyrazole | 166820-34-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-(Benzyloxy)-5-bromopyrazole
• 英文别名: 5-Bromo-1-phenylmethoxypyrazole
• CAS: 166820-34-4
• 化学式: C₁₀H₉BrN₂O
• 分子量: 253.098
• InChiKey: VMNQMBXFLDGSMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Benzyloxy)-5-bromopyrazole 在 一氯化碘 、 potassium carbonate 作用下， 以 氯仿 为溶剂， 以21%的产率得到1-benzyloxy-5-bromo-4-iodopyrazole
  参考文献：
  名称：

  Novel 5-substituted 1-pyrazolol analogues of ibotenic acid: Synthesis and pharmacology at glutamate receptors

  摘要：

  5-Substituted 1-pyrazolol analogues of ibotenic acid have been synthesized and pharmacologically characterized on ionotropic and metabotropic glutamate receptors (iGluRs and mGluRs). The syntheses involved introduction of bromide, alkyls, phenyl and arylalkyls in the 5-position of 1-benzyloxypyrazole leading to 5-substituted (RS)-2-amino-(1-hydroxy-4-pyrazolyl)acetic acids (5a-1). The pharmacological activities of the synthesized analogues ranged from the 5-cyclopropylmethyl analogue (5f) with weak but selective affinity for NMDA receptors (IC50 = 35 mu M), over the 5-n-propyl analogue (5c), which was a selective mGluR2 agonist (EC50 = 72 mu M), to the 5-cyclohexylmethyl analogue (5g), which was a selective mGluR2 antagonist (K-i = 32 mu M), and the 5-phenylethyl analogue (5j), which was a weak but apparently selective mGluR1 antagonist (K-i = 230 mu M). This series of compounds afforded GluR ligands with a broad spectrum of pharmacological profiles, and showing potential for development of new compounds with subtype-selective activities at various GluRs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.047
• 作为产物：
  描述：

  1-(苄氧基)吡唑 在 正丁基锂 、 四溴化碳 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 以81%的产率得到1-(Benzyloxy)-5-bromopyrazole
  参考文献：
  名称：

  Novel 5-substituted 1-pyrazolol analogues of ibotenic acid: Synthesis and pharmacology at glutamate receptors

  摘要：

  5-Substituted 1-pyrazolol analogues of ibotenic acid have been synthesized and pharmacologically characterized on ionotropic and metabotropic glutamate receptors (iGluRs and mGluRs). The syntheses involved introduction of bromide, alkyls, phenyl and arylalkyls in the 5-position of 1-benzyloxypyrazole leading to 5-substituted (RS)-2-amino-(1-hydroxy-4-pyrazolyl)acetic acids (5a-1). The pharmacological activities of the synthesized analogues ranged from the 5-cyclopropylmethyl analogue (5f) with weak but selective affinity for NMDA receptors (IC50 = 35 mu M), over the 5-n-propyl analogue (5c), which was a selective mGluR2 agonist (EC50 = 72 mu M), to the 5-cyclohexylmethyl analogue (5g), which was a selective mGluR2 antagonist (K-i = 32 mu M), and the 5-phenylethyl analogue (5j), which was a weak but apparently selective mGluR1 antagonist (K-i = 230 mu M). This series of compounds afforded GluR ligands with a broad spectrum of pharmacological profiles, and showing potential for development of new compounds with subtype-selective activities at various GluRs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.047

文献信息

• Synthesis of 5-Substituted 1-Hydroxypyrazoles through Directed Lithiation of 1-(Benzyloxy)pyrazole
  作者：Per Vedso、Mikael Begtrup

  DOI：10.1021/jo00121a017

  日期：1995.8

  1-Hydroxypyrazoles have been converted to 1-(benzyloxy), [(9-phenylfluorenyl)oxy], [(N,N-diethylcarbamoyl)oxy], and (-silyloxy)pyrazoles. 1-(Benzyloxy)pyrazole was lithiated selectively in the 5-position. Subsequent reaction with electrophiles gives rise to 1-(benzyloxy)pyrazole with carbon, halogen, silicon, sulfur, or tin substituents at the 5-position. 1-(Benzyloxy)pyrazoles could be debenzylated by hydrogen bromide or hydrogenolysis producing 5-substituted 1-hydroxypyrazoles in high overall yield.