1-甲基-5-(2-噻吩)-1H-吡唑 | 876316-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-5-(2-噻吩)-1H-吡唑
• 英文名称: 1-methyl-5-(2-thienyl)-1H-pyrazole
• 英文别名: 1-methyl-5-(thiophen-2-yl)-1H-pyrazole；1-methyl-5-thiophen-2-ylpyrazole
• CAS: 876316-68-6
• 化学式: C₈H₈N₂S
• 分子量: 164.231
• InChiKey: YTGTYWLNJQJMIP-UHFFFAOYSA-N

物化性质

• 沸点：
  278.3±15.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基-5-(2-噻吩)-1H-吡唑 在 sodium hydroxide 、 正丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 2: Synthesis and inhibitory activity of aryl-3-trifluoromethylpyrazoles

  摘要：

  To identify potent and selective calcium-release-activated calcium (CRAG) channel inhibitors, we examined the structure-activity relationships of the pyrazole and thiophene moieties in compound 4. Compound 25b was found to exhibit highly potent and selective inhibitory activity for CRAC channels and further modifications of the pyrazole and benzoyl moieties of compound 25b produced compound 29. These compounds were potent inhibitors of IL-2 production in vitro and also acted as inhibitors in pharmacological models of diseases resulting from T-lymphocyte activation, after oral administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.039
• 作为产物：
  描述：

  2-噻吩基锂 、 5-碘-1-甲基-1H-吡唑 在 四(三苯基膦)钯 indium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到1-甲基-5-(2-噻吩)-1H-吡唑
  参考文献：
  名称：

  铟介导的杂二芳基合成

  摘要：

  三有机铟试剂与有机亲电子试剂之间的钯介导的偶联反应扩展到杂芳族化合物的合成。富电子杂环和贫电子杂环都可以用作有机亲电子试剂或有机铟衍生物。

  DOI：

  10.1021/jo062638k

文献信息

• HETEROCYCLIC MGLU5 ANTAGONISTS
  申请人：Recordati Ireland Limited

  公开号：EP2477981A1

  公开（公告）日：2012-07-25
• Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 2: Synthesis and inhibitory activity of aryl-3-trifluoromethylpyrazoles
  作者：Yasuhiro Yonetoku、Hirokazu Kubota、Yoshinori Okamoto、Jun Ishikawa、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2006.03.039

  日期：2006.8

  To identify potent and selective calcium-release-activated calcium (CRAG) channel inhibitors, we examined the structure-activity relationships of the pyrazole and thiophene moieties in compound 4. Compound 25b was found to exhibit highly potent and selective inhibitory activity for CRAC channels and further modifications of the pyrazole and benzoyl moieties of compound 25b produced compound 29. These compounds were potent inhibitors of IL-2 production in vitro and also acted as inhibitors in pharmacological models of diseases resulting from T-lymphocyte activation, after oral administration. (c) 2006 Elsevier Ltd. All rights reserved.
• Indium-Mediated Synthesis of Heterobiaryls
  作者：Enrique Font-Sanchis、F. Javier Céspedes-Guirao、Ángela Sastre-Santos、Fernando Fernández-Lázaro

  DOI：10.1021/jo062638k

  日期：2007.4.1

  The palladium-mediated coupling reaction between triorganoindium reagents and organic electrophiles is extended to the synthesis of heteroaromatic compounds. Both electron-rich and electron-poor heterocycles can act as the organic electrophile or as the organoindium derivative.

  三有机铟试剂与有机亲电子试剂之间的钯介导的偶联反应扩展到杂芳族化合物的合成。富电子杂环和贫电子杂环都可以用作有机亲电子试剂或有机铟衍生物。