5-(4-chlorobutyl)-3-phenyl-1H-pyrazole | 1448862-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorobutyl)-3-phenyl-1H-pyrazole
• CAS: 1448862-52-9
• 化学式: C₁₃H₁₅ClN₂
• 分子量: 234.728
• InChiKey: YMKSOJRRSRNXLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(4-chlorobutyl)-3-phenyl-1H-pyrazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  A novel series of metabotropic glutamate receptor 5 negative allosteric modulators based on a 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine core

  摘要：

  A series of potent non-acetylinic negative allosteric modulators of the metabotropic glutamate receptor 5 (mGlu5 NAMs) was developed starting from HTS screening hit 1. Potency was improved via iterative SAR, and physicochemical properties were optimized to deliver orally bioavailable compounds acceptable for in vivo testing. A lead molecule from the series demonstrated dose-dependent activity in the second phase of the rat formalin test from 30 mg/kg, and a preliminary PK/PD relationship was established. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.044
• 作为产物：
  描述：

  (E)-3,7-dichloro-1-phenylhept-2-en-1-one 在 三乙烯二胺 、 一水合肼 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以26%的产率得到5-(4-chlorobutyl)-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  Highly Regioselective Synthesis of 1-Acyl-5-hydroxypyrazolines or Synthesis of 3,5-Disubstituted Pyrazoles from (E)-β-Chlorovinyl Ketones and Benzohydrazides or Hydrazine Hydrate

  摘要：

  Highly regioselective synthesis of 1-acyl-5-hydroxypyrazolines or synthesis of 3,5-disubstituted pyrazoles have been achieved through the cyclocondensation of (E)/beta-chlorovinyl ketones with benzohydrazides/hydrazine hydrate under extremely mild reaction conditions. The mechanistic studies showed that diverse electrophilic pathways of (E)-beta-chlorovinyl ketones could be observed by using different nucelophilic species. Moreover, the utility of the tandem reaction is further illustrated by the concise synthesis of 1-acyl-pyrazole and 3-pentyl-5-phenyl-1H-pyrazole.

  DOI：

  10.3987/com-20-14251