3-溴-2-(三氟甲基)咪唑并[1,2-a]吡啶 | 503172-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 3-溴-2-(三氟甲基)咪唑并[1,2-a]吡啶
• 英文名称: 3-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine
• CAS: 503172-42-7
• 化学式: C₈H₄BrF₃N₂
• 分子量: 265.032
• InChiKey: UWFXWNIDZUWCAY-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100°
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-溴-2-(三氟甲基)咪唑并[1,2-a]吡啶 、 对甲酰基苯甲酸甲酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Potent, selective, orally bioavailable inhibitors of tumor necrosis factor-α converting enzyme (TACE): Discovery of indole, benzofuran, imidazopyridine and pyrazolopyridine P1′ substituents

  摘要：

  Potent and selective inhibitors of tumor necrosis factor-a converting enzyme ( TACE) were discovered with several new heterocyclic P1' groups in conjunction with cyclic beta-amino hydroxamic acid scaffolds. Among them, the pyrazolopyridine provided the best overall profile when combined with tetrahydropyran beta-amino hydroxamic acid scaffold. Specifically, inhibitor 49 showed IC50 value of 1 nM against porcine TACE and 170 nM in the suppression of LPS-induced TNF-alpha of human whole blood. Compound 49 also displayed excellent selectivity over a wide panel of MMPs as well as excellent oral bioavailability (F% > 90%) in rat n-in-1 PK studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.120
• 作为产物：
  描述：

  2-(三氟甲基)咪唑并[1,2-a]吡啶 在 四溴化碳 、 tetrabutylammonium tetrafluoroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 以82%的产率得到3-溴-2-(三氟甲基)咪唑并[1,2-a]吡啶
  参考文献：
  名称：

  阳极氧化和阴极还原的协同作用导致电化学CH卤化

  摘要：

  我们在本文中发现了电化学的CH卤化方案，该方案协同结合了阳极氧化和阴极还原以形成C-X键。在无外源氧化剂的条件下证明了该反应。此外，这是在电化学条件下活化CBr 4，CHBr 3和CCl 3 Br的第一个例子。

  DOI：

  10.1002/cjoc.201900091

文献信息

• NOVEL FUSED CYCLIC COMPOUND AND USE THEREOF
  申请人：Negoro Nobuyuki

  公开号：US20120172351A1

  公开（公告）日：2012-07-05

  A compound represented by the formula (I): wherein each symbol is as defined in the specification, and a salt thereof have a GPR40 receptor activation action and is useful as an insulin secretagogue or a prophylactic or therapeutic drug for diabetes and the like.

  化合物的化学式为(I)，其中每个符号如规范所定义，其盐具有GPR40受体激活作用，并可用作胰岛素分泌剂或糖尿病等的预防或治疗药物。
• Synergy of Anodic Oxidation and Cathodic Reduction Leads to Electrochemical C—H Halogenation
  作者：Zhilin Zhou、Yong Yuan、Yangmin Cao、Jin Qiao、Anjin Yao、Jing Zhao、Wanqing Zuo、Wenjie Chen、Aiwen Lei

  DOI：10.1002/cjoc.201900091

  日期：2019.6

  We herein uncovered an electrochemical C—H halogenation protocol that synergistically combines anodic oxidation and cathodic reduction for C—X bond formation. The reaction was demonstrated under exogenous‐oxidant‐free conditions. Moreover, this is the first example of activating CBr4, CHBr3, and CCl3Br under electrochemical conditions.

  我们在本文中发现了电化学的CH卤化方案，该方案协同结合了阳极氧化和阴极还原以形成C-X键。在无外源氧化剂的条件下证明了该反应。此外，这是在电化学条件下活化CBr 4，CHBr 3和CCl 3 Br的第一个例子。
• Potent, selective, orally bioavailable inhibitors of tumor necrosis factor-α converting enzyme (TACE): Discovery of indole, benzofuran, imidazopyridine and pyrazolopyridine P1′ substituents
  作者：Zhonghui Lu、Gregory R. Ott、Rajan Anand、Rui-Qin Liu、Maryanne B. Covington、Krishna Vaddi、Mingxin Qian、Robert C. Newton、David D. Christ、James Trzaskos、James J.-W. Duan

  DOI：10.1016/j.bmcl.2008.01.120

  日期：2008.3

  Potent and selective inhibitors of tumor necrosis factor-a converting enzyme ( TACE) were discovered with several new heterocyclic P1' groups in conjunction with cyclic beta-amino hydroxamic acid scaffolds. Among them, the pyrazolopyridine provided the best overall profile when combined with tetrahydropyran beta-amino hydroxamic acid scaffold. Specifically, inhibitor 49 showed IC50 value of 1 nM against porcine TACE and 170 nM in the suppression of LPS-induced TNF-alpha of human whole blood. Compound 49 also displayed excellent selectivity over a wide panel of MMPs as well as excellent oral bioavailability (F% > 90%) in rat n-in-1 PK studies. (C) 2008 Elsevier Ltd. All rights reserved.