1-苄氧基-4-氯吡唑 | 1040283-74-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 1-苄氧基-4-氯吡唑
• 英文名称: 1-benzyloxy-4-chloropyrazole
• 英文别名: 4-Chloro-1-phenylmethoxypyrazole；4-chloro-1-phenylmethoxypyrazole
• CAS: 1040283-74-6
• 化学式: C₁₀H₉ClN₂O
• 分子量: 208.647
• InChiKey: NEZRZLCCIASMRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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-苄氧基-4-氯吡唑 、 2-(N-tert-butoxycarbonylimino)malonic acid diethyl ester 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.08h， 以76%的产率得到diethyl 2-(1-benzyloxy-4-chloropyrazol-5-yl)-2-tert-butyloxycarbonylaminomalonate
  参考文献：
  名称：

  N-Hydroxypyrazolyl Glycine Derivatives as Selective N-Methyl-d-aspartic Acid Receptor Ligands

  摘要：

  A series of analogues based on N-hydroxypyrazole as a bioisostere for the distal carboxylate group of aspartate have been designed, synthesized, and pharmacologically characterized. Affinity studies on the major glutamate receptor subgroups show that these 4-substituted N-hydroxypyrazol-5-yl glycine (NHP5G) derivatives are selectively recognized by N-methyl-D-aspartic acid (NMDA) receptors and that the (R)enantiomers are preferred. Moreover, several of the compounds are able to discriminate between individual subtypes among the NMDA receptors, providing new pharmacological tools. For example, 4-propyl NHP5G is an antagonist at the NR1/NR2A subtype but an agonist at the NR1/NR2D subtype. Molecular docking studies indicate that the substituent protrudes into a region that may be further exploited to improve subtype selectivity, thereby opening up a design strategy for ligands which can differentiate individual NMDA receptor subtypes.

  DOI：

  10.1021/jm800025e
• 作为产物：
  描述：

  1-(苄氧基)吡唑 在 磺酰氯 作用下， 以 乙醚 为溶剂， 以3.51 g的产率得到1-苄氧基-4-氯吡唑
  参考文献：
  名称：

  N-Hydroxypyrazolyl Glycine Derivatives as Selective N-Methyl-d-aspartic Acid Receptor Ligands

  摘要：

  A series of analogues based on N-hydroxypyrazole as a bioisostere for the distal carboxylate group of aspartate have been designed, synthesized, and pharmacologically characterized. Affinity studies on the major glutamate receptor subgroups show that these 4-substituted N-hydroxypyrazol-5-yl glycine (NHP5G) derivatives are selectively recognized by N-methyl-D-aspartic acid (NMDA) receptors and that the (R)enantiomers are preferred. Moreover, several of the compounds are able to discriminate between individual subtypes among the NMDA receptors, providing new pharmacological tools. For example, 4-propyl NHP5G is an antagonist at the NR1/NR2A subtype but an agonist at the NR1/NR2D subtype. Molecular docking studies indicate that the substituent protrudes into a region that may be further exploited to improve subtype selectivity, thereby opening up a design strategy for ligands which can differentiate individual NMDA receptor subtypes.

  DOI：

  10.1021/jm800025e