2-(3-溴苯基)-5-苯基-2H-吡唑-3-胺 | 890764-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(3-溴苯基)-5-苯基-2H-吡唑-3-胺
• 中文别名: 1-(3-溴苯基)-3-苯基-1H-吡唑-5-胺
• 英文名称: 5-amino-1-(3-bromophenyl)-3-phenyl-1H-pyrazole
• 英文别名: 1-(3-Bromophenyl)-3-phenyl-1H-pyrazol-5-amine；2-(3-bromophenyl)-5-phenylpyrazol-3-amine
• CAS: 890764-15-5
• 化学式: C₁₅H₁₂BrN₃
• 分子量: 314.184
• InChiKey: PHIHEAAALRUYFH-UHFFFAOYSA-N

物化性质

• 沸点：
  500.8±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  2-(3-溴苯基)-5-苯基-2H-吡唑-3-胺 在 碘苯二乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以92%的产率得到(Z)-3-((E)-(3-bromophenyl)diazenyl)-3-phenylacrylonitrile
  参考文献：
  名称：

  PIDA-mediated oxidative aromatic C N bond cleavage: Efficient methodology for the synthesis of 1,2-diaza-1,3-dienes under ambient conditions

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153252
• 作为产物：
  描述：

  苯甲腈 在 盐酸 、 potassium tert-butylate 作用下， 以 苯 为溶剂， 反应 24.33h， 生成 2-(3-溴苯基)-5-苯基-2H-吡唑-3-胺
  参考文献：
  名称：

  Substituent Effects of N-(1,3-Diphenyl-1H-pyrazol-5-yl)benzamides on Positive Allosteric Modulation of the Metabotropic Glutamate-5 Receptor in Rat Cortical Astrocytes

  摘要：

  CDPPB [3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl) benzamide] was recently described as the first centrally active, positive allosteric modulator of rat and human metabotropic glutamate receptor (mGluR) mGluR(5) subtype. We explored the structural requirements for potentiation of glutamate-induced calcium release in naturally expressed mGluR5 in cultured rat astrocytes and increasing affinity for the allosteric antagonist binding site by evaluating 50 analogues of CDPPB. In the fluorometric calcium assay, CDPPB exhibited an EC50 value of 77 +/- 15 nM in potentiating mGluR(5)-mediated responses in cortical astrocytes and a K-i value of 3760 ( 430 nM in displacing [H-3] methoxyPEPy binding in membranes of cultured HEK-293 cells expressing rat mGluR5. The structure-activity relationships showed that electronegative aromatic substituents in the para-position of the benzamide moiety of CDPPB increase potency. Both binding and functional activities were further increased with a halogen atom in the ortho-position of the 1-phenyl ring. These effects of substitution do not match those of either aromatic ring of MPEP [2-methyl-6-(phenylethynyl)-pyridine] for the antagonist allosteric binding site. Combination of the optimal substituents and aromatic positions resulted in 4-nitro-N-(1-(2-fluorophenyl)-3-phenyl-1H-pyrazol-5-yl) benzamide (VU-1545) showing K-i) 156 (29 nM and EC50) 9.6 (1.9 nM in the binding and functional assays, respectively.

  DOI：

  10.1021/jm051252j

文献信息

• Synthesis, characterization and application of magnetic biochar sulfonic acid as a highly efficient recyclable catalyst for preparation of spiro-pyrazolo[3,4-b]pyridines
  作者：Li-Na Dong、Shuai-Zheng Zhang、Wan-Lu Zhang、Yao Dong、Li-Ping Mo、Zhan-Hui Zhang

  DOI：10.1007/s11164-022-04660-6

  日期：2022.3

  microscope, transmission electron microscope and vibrating sample magnetometer techniques. The prepared catalyst exhibited excellent catalytic activity for synthesis of spiro-pyrazolo[3,4-b]pyridine derivatives via one-pot three-component reaction of 1H-pyrazol-5-amine, isatin and 3-oxo-3-phenylpropanenitrile. The catalyst could be readily recovered and reused several times without an obvious decay of

  采用傅里叶红外光谱(FT-IR)、粉末X射线衍射技术、扫描电镜、透射电镜和振动样品磁强计技术制备磁性生物炭磺酸并对其进行表征。制备的催化剂对1 H-吡唑-5-胺、靛红和3-氧代-3-苯基丙腈的一锅三组分反应合成螺吡唑并[3,4- b ]吡啶衍生物表现出优异的催化活性。该催化剂可以很容易地回收和多次重复使用，而催化性能没有明显下降。
• Nickel supported on magnetic biochar as a highly efficient and recyclable heterogeneous catalyst for the one‐pot synthesis of spirooxindole‐dihydropyridines
  作者：Li‐Na Dong、Ya‐Meng Wang、Wan‐Lu Zhang、Li‐Ping Mo、Zhan‐Hui Zhang

  DOI：10.1002/aoc.6667

  日期：2022.5

  prepared catalyst. The prepared catalyst exhibited excellent catalytic activity for synthesis of spirooxindole-dihydropyridines derivatives by a one-pot three-component reaction of isatin, barbituric acid, and 6-amino uracil or 1H-pyrazol-5-amine. This new methodology demonstrated some important features, including high yields, lower loading of the catalyst, easy work-up, and recyclability of the catalyst

  磁性材料因其易于分离和良好的可重复使用性而在多相催化中显示出广阔的应用前景。本工作报告了一种新型磁性生物炭负载镍催化剂的设计、合成和表征。采用傅里叶红外光谱（FT-IR）、粉末X射线衍射技术（XRD）、扫描电子显微镜（SEM）、透射电子显微镜（TEM）和振动样品磁力计（VSM）技术对制备的催化剂进行分析。所制备的催化剂对靛红、巴比妥酸和6-氨基尿嘧啶或1 H的一锅三组分反应合成螺氧吲哚-二氢吡啶类衍生物表现出优异的催化活性。-吡唑-5-胺。这种新方法展示了一些重要特征，包括高产率、较低的催化剂负载、易于后处理以及催化剂可回收至少六次而催化性能没有明显下降。
• Tandem Oxidative Reaction of 1,3-Diarylpropenes and 5-Aminopyrazoles
  作者：Dongping Cheng、Jing-Hua Li、Xiaoliang Xu、Huafang Gu、Hongshuang Xia、Yawei Wang

  DOI：10.1055/a-2145-5916

  日期：2023.12

  The reaction of 5-aminopyrazoles with 1,3-diarylpropenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, with subsequent intramolecular cyclization and dehydroaromatization in the presence of Cu(OTf)2/tert-butyl hydroperoxide, gave a series of pyrazolo[3,4-b]pyridines in moderate to excellent yields. The reaction has the advantages of high atom economy, a wide substrate scope, and a one-pot procedure.

  摘要在 2,3-二氯-5,6-二氰基-1,4-苯醌介导下，5-氨基吡唑与 1,3-二芳基丙烯发生反应，随后在 Cu(OTf)2/ 叔丁基过氧化氢存在下发生分子内环化和脱氢芳香化反应，得到一系列吡唑并[3,4-b]吡啶，收率中等到极好。该反应具有原子经济性高、底物范围广和一锅反应等优点。
• Asymmetric Synthesis of Axially Chiral Arylpyrazole via an Organocatalytic Arylation Reaction
  作者：Xi Gao、Chengwen Li、Li Chen、Xin Li

  DOI：10.1021/acs.orglett.3c02694

  日期：2023.10.27

  enantioselective arylation reaction of 3-aryl-5-aminopyrazoles and quinone derivatives was realized using a chiral phosphoric acid catalyst under mild conditions. The reaction has a broad scope with respect to both arylation reaction partners and hence offers rapid access to an array of axially chiral arylpyrazoles with pretty outcomes (up to 95% yield and 99% ee). Notably, the reaction is very efficient

  在此，使用手性磷酸催化剂在温和条件下实现了3-芳基-5-氨基吡唑和醌衍生物的高度对映选择性芳基化反应。该反应对于芳基化反应伙伴而言具有广泛的范围，因此可以快速获得一系列轴向手性芳基吡唑，并获得良好的结果（高达 95% 的产率和 99% ee）。值得注意的是，该反应非常有效，因为模型反应的催化剂负载量可以减少至 1 mol%，并且仍然保持对映选择性。此外，通过克级反应和产物的转化证明了该方案的合成实用性。
• Enantioselective α-Amination of Amides by One-Pot Organo-/Iodine Sequential Catalysis
  作者：Liang Bai、Jian-Sheng Wei、Ling-Yi Zhong、Ao-Qiang Ma、Jian Wang、Zhi-Qiang Du、Ai-Bao Xia、Dan-Qian Xu

  DOI：10.1021/acs.orglett.3c03925

  日期：2024.1.12

  An one-pot organo- and iodine sequential catalysis strategy for reactions of amides with pyrazole-based primary amines was described to synthesize chiral α-amino amides with a quaternary stereocenter. This methodology exhibited strong asymmetric induction, resulting in a typical enantiomeric excess value exceeding 99% and diastereoselectivity up to >99:1 dr. Moreover, the reaction was conducted without

  描述了酰胺与吡唑基伯胺反应的一锅有机和碘顺序催化策略，以合成具有四元立构中心的手性 α-氨基酰胺。该方法表现出强烈的不对称诱导，导致典型的对映体过量值超过 99%，非对映选择性高达 >99:1 dr。此外，该反应在不使用任何金属或强碱的情况下进行。