1-苄基-4-溴咪唑 | 106848-38-8

• 物质功能分类: 有机原料 - 杂环化合物
• 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-苄基-4-溴咪唑
• 英文名称: 1-benzyl-4-bromo-1H-imidazole
• 英文别名: 1-benzyl-4-bromoimidazole
• CAS: 106848-38-8
• 化学式: C₁₀H₉BrN₂
• 分子量: 237.099
• InChiKey: SEDUHBKZBAORFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  1-苄基-4-溴咪唑 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 以65%的产率得到N-苄基咪唑
  参考文献：
  名称：

  NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

  摘要：

  DOI：

  10.1016/j.molcata.2014.06.012
• 作为产物：
  描述：

  1-苄基-2,4,5-三溴-1H-咪唑 在 正丁基锂 、 水 作用下， 生成 1-苄基-4-溴咪唑
  参考文献：
  名称：

  方便合成4（5）-单-，4,5-二-和2,4,5-三取代的咪唑

  摘要：

  描述了一种通过卤素-金属交换技术，通过FGI将2-被保护的2,4,5-三溴咪唑中的溴原子按2→5→4的顺序逐步引入取代基（包括氢）到咪唑环中的方法。

  DOI：

  10.1016/s0040-4039(00)84334-8

文献信息

• A General, Practical Palladium-Catalyzed Cyanation of (Hetero)Aryl Chlorides and Bromides
  作者：Todd D. Senecal、Wei Shu、Stephen L. Buchwald

  DOI：10.1002/anie.201304188

  日期：2013.9.16

  Playing it safe: The nontoxic cyanide source K4[Fe(CN)6]⋅3 H2O can be used for the cyanation of (hetero)aryl halides. The application of palladacycle catalysts prevents poisoning during catalyst formation, thereby allowing for low catalyst loadings, fast reaction times, and wide heterocyclic substrate scope.

  安全操作：无毒氰化物源 K 4 [Fe(CN) 6 ]⋅3 H 2 O 可用于（杂）芳基卤化物的氰化。钯环催化剂的应用可防止催化剂形成过程中中毒，从而实现低催化剂负载、快速反应时间和广泛的杂环底物范围。
• Exploring the Orthosteric Binding Site of the γ-Aminobutyric Acid Type A Receptor Using 4-(Piperidin-4-yl)-1-hydroxypyrazoles 3- or 5-Imidazolyl Substituted: Design, Synthesis, and Pharmacological Evaluation
  作者：Jacob Krall、Claus H. Jensen、Troels E. Sørensen、Birgitte Nielsen、Anders A. Jensen、Tommy Sander、Thomas Balle、Bente Frølund

  DOI：10.1021/jm4006466

  日期：2013.8.22

  A series of 4-(piperidin-4-yl)-1-hydroxypyrazole (4-PHP) 3- or 5-imidazolyl substituted analogues have been designed, synthesized, and characterized pharmacologically. All analogues showed binding affinities in the low micro- to low nanomolar range at native rat GABAA receptors and were found to be antagonists at the human α1β2γ2s receptor. The structure–activity relationship of the compound series

  已经设计，合成和表征了一系列4-（哌啶-4-基）-1-羟基吡唑（4-PHP）3-或5-咪唑基取代的类似物。所有的类似物表现出结合亲和力的低微以低纳摩尔范围在天然大鼠GABA甲受体和被认为是在人α拮抗剂1 β 2 γ 2S受体。该化合物系列的结构-活性关系表明，在正构结合位点4-PHP支架附近，先前发现的腔在大小和结构上存在明显差异。
• A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles
  作者：Mingjuan Su、Stephen L. Buchwald

  DOI：10.1002/anie.201201244

  日期：2012.5.7

  The first palladium‐catalyzed amidation of five‐membered heterocyclic bromides with multiple heteroatoms was achieved using the Pd/1 catalyst system. N‐Arylated imidazoles, pyrazoles, thiazoles, pyrroles, and thiophenes were synthesized in moderate to excellent yield. Experimental results and DFT calculations point to the need for an electron‐rich and sterically demanding biaryl phosphine ligand to

  令人难以置信的体积：使用 Pd/ 1催化剂体系实现了具有多个杂原子的五元杂环溴化物的首次钯催化酰胺化。N-芳基化咪唑、吡唑、噻唑、吡咯和噻吩以中等至优异的产率合成。实验结果和 DFT 计算表明需要富含电子且空间要求高的联芳膦配体来促进这些困难的反应。
• A convenient synthesis of 4(5)-mono-, 4,5-di-, and 2,4,5-tri-substituted imidazoles
  作者：Brian Iddon、Nazir Khan

  DOI：10.1016/s0040-4039(00)84334-8

  日期：1986.1

  A procedure is described for the stepwise introduction of substituents (hydrogen included) into the imidazole ring by FGI of the bromine atoms in 1-protected 2,4,5-tribromoimidazoles in the order 2 → 5 → 4 using halogen-metal exchange techniques.

  描述了一种通过卤素-金属交换技术，通过FGI将2-被保护的2,4,5-三溴咪唑中的溴原子按2→5→4的顺序逐步引入取代基（包括氢）到咪唑环中的方法。
• Novel and potent 3-(2,3-dichlorophenyl)-4-(benzyl)-4H-1,2,4-triazole P2X7 antagonists
  作者：William A. Carroll、Douglas M. Kalvin、Arturo Perez Medrano、Alan S. Florjancic、Ying Wang、Diana L. Donnelly-Roberts、Marian T. Namovic、George Grayson、Prisca Honoré、Michael F. Jarvis

  DOI：10.1016/j.bmcl.2007.04.075

  日期：2007.7

  Structure-activity relationship (SAR) studies were conducted around early tetrazole-based leads 3 and 4. Replacements for the tetrazole core were investigated and the pendant benzyl substitution was reoptimized with a triazole isostere. Triazole-based P2X(7) antagonists were identified with similar potency to the lead compound 4 but with improved physiochemical properties. Compound 12 was active in a rat model of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.