1-(2-溴苯基)-3,5-二甲基吡唑 | 1155573-50-4

• 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-(2-溴苯基)-3,5-二甲基吡唑
• 英文名称: 1-(2-bromophenyl)-3,5-dimethyl-1H-pyrazole
• 英文别名: 1-(2-bromophenyl)-3,5-dimethylpyrazole
• CAS: 1155573-50-4
• 化学式: C₁₁H₁₁BrN₂
• 分子量: 251.126
• InChiKey: YIRGHOVEEWNTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-(2-溴苯基)-3,5-二甲基吡唑 在 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.83h， 生成
  参考文献：
  名称：

  Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes

  摘要：

  In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.11.008
• 作为产物：
  描述：

  2-溴苯肼盐酸盐 、 乙酰丙酮 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到1-(2-溴苯基)-3,5-二甲基吡唑
  参考文献：
  名称：

  Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes

  摘要：

  In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.11.008

文献信息

• An environmentally benign and efficient synthesis of 4‐Selanylpyrazoles catalyzed by haloid salts in water
  作者：Yingguo Fang、Junxing Wang、Yuhong Liu、Jie Yan

  DOI：10.1002/aoc.4921

  日期：2019.6

  An environmentally benign procedure is developed for the preparation of 4‐selanylpyrazoles from pyrazoles and diselenides. Using haloid salts as catalysts and H2O2 as oxidant, this catalytic protocol is convenient in water at room temperature under open‐air condition, and is suitable for a wide variety of starting materials and provides a series of 4‐selanylpyrazoles in good yields. A plausible catalytic

  开发了一种环境友好的程序，用于从吡唑和二硒化物制备4-硒基吡唑。使用卤素盐作为催化剂，H 2 O 2作为氧化剂，该催化方案在室温，露天条件下的水中非常方便，适用于多种起始原料，并提供了一系列产率高的4-硒基吡唑。推测可能的催化亲电取代机理。
• Iodine-mediated synthesis of 4-selanylpyrazoles
  作者：Junxing Wang、Yuhong Liu、Jie Yan

  DOI：10.1039/c8nj02629g

  日期：——

  A new and simple procedure mediated by I₂ is developed for the preparation of 4-selanylpyrazoles from pyrazoles and diselenides.

  通过I₂介导的一种新的简单程序，用于从吡唑和二硒化物制备4-硒代吡唑。
• Oxone-DMSO Triggered Methylene Insertion and C(sp²)−C(sp³)-H−C(sp²) Bond Formation to Access Functional Bis-Heterocycles
  作者：Jaspreet Kour、Vunnam Venkateswarlu、Praveen K. Verma、Yaseen Hussain、Gurudutt Dubey、Prasad V. Bharatam、Subash C. Sahoo、Sanghapal D. Sawant

  DOI：10.1021/acs.joc.9b03477

  日期：2020.4.3

  Metal-free insertion of a methylene group was achieved for the construction of a new C(sp2)–C(sp3)-H–C(sp2) bond in order to prepare novel bis-heterocyclic scaffolds. The complete mechanistic investigations included experimental study and DFT calculations, and various symmetric and unsymmetric bis-pyrazoles as well as other pyrazole-based bis-heterocyclic molecules were prepared in moderate to high

  为了制备新型的双杂环支架，实现了新的C（sp 2）–C（sp 3）-H–C（sp 2）键的构建，实现了无金属亚甲基的插入。完整的机理研究包括实验研究和DFT计算，并且以中等到高产率制备了各种对称和不对称的双吡唑以及其他基于吡唑的双杂环分子。不对称吡唑中桥连亚甲基的进一步修饰产生了手性中心，从而扩展了该方法的范围。
• Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes
  作者：Debajyoti Saha、Raju Ghosh、Ranjan Dutta、Achintya Kumar Mandal、Amitabha Sarkar

  DOI：10.1016/j.jorganchem.2014.11.008

  日期：2015.1

  In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design. (C) 2014 Elsevier B.V. All rights reserved.