5-chloro-4-phenyl-1H-1,2,3-triazole | 1204351-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-4-phenyl-1H-1,2,3-triazole
• 英文别名: 4-chloro-5-phenyl-2H-triazole
• CAS: 1204351-89-2
• 化学式: C₈H₆ClN₃
• 分子量: 179.609
• InChiKey: HAGKPLJGVTZUAH-UHFFFAOYSA-N

物化性质

• 沸点：
  351.3±22.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-4-phenyl-1H-1,2,3-triazole 、 2-溴丙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到ethyl 2-(5-bromo-4-phenyl-1H-1,2,3-triazol-1-yl)propanoate
  参考文献：
  名称：

  Facile and direct halogenation of 1,2,3-triazoles promoted by a KX–oxone system under transition metal free conditions

  摘要：

  在无过渡金属条件下，可以在常温下方便高效地对4-芳基1,2,3-三唑进行氧化卤化。

  DOI：

  10.1039/d0nj05170e
• 作为产物：
  描述：

  4-苯基-1,2,3-三氮唑 在 Oxone 、 potassium chloride 作用下， 以 乙腈 为溶剂， 以88%的产率得到5-chloro-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Facile and direct halogenation of 1,2,3-triazoles promoted by a KX–oxone system under transition metal free conditions

  摘要：

  在无过渡金属条件下，可以在常温下方便高效地对4-芳基1,2,3-三唑进行氧化卤化。

  DOI：

  10.1039/d0nj05170e

文献信息

• Highly N²-Selective Coupling of 1,2,3-Triazoles with Indole and Pyrrole
  作者：Jian Wen、Li-Li Zhu、Qing-Wei Bi、Zhu-Qing Shen、Xiao-Xiao Li、Xin Li、Zhen Wang、Zili Chen

  DOI：10.1002/chem.201302761

  日期：2014.1.20

  Hydrogen‐bond mediated coupling of 1,2,3‐triazoles to indoles and pyrroles results in N2 selective functionalization of the triazole moiety in moderate to excellent yields. The reaction was tolerant of un‐, mono‐ and disubstituted triazoles and was applied to synthesize tryptophan derived fluorescent amino acids.

  氢键介导的1,2,3-三唑与吲哚和吡咯的偶合导致三唑部分的N2选择性官能化，产率中等至优异。该反应可耐受未取代，单取代和双取代的三唑，可用于合成色氨酸衍生的荧光氨基酸。
• Reducing Platelet Activation, Aggregation and Platelet-Stimulated Thrombosis or Blood Coagulation by Reducing Mitochondrial Respiration
  申请人：Collman James P.

  公开号：US20110301180A1

  公开（公告）日：2011-12-08

  It has been discovered that inhibiting mitochondrial respiration in platelets reduces platelet activation or platelet aggregation. Certain heterocyclic compounds significantly reduced one or more platelet functions including clumping, sticking or platelet-stimulated clotting. Thus diseases or disorders mediated by inappropriately high levels of platelet activation or platelet aggregation can be treated by administering a therapeutically effective amount of a heterocyclic compound or nonheterocyclic mitochondrial inhibitor that significantly reduces one or more platelet functions including clumping, sticking or platelet-stimulated clotting, preferably in a reversible manner.

  已经发现，在血小板中抑制线粒体呼吸可以减少血小板的激活或血小板聚集。某些杂环化合物显著降低了一个或多个血小板功能，包括凝聚、粘附或血小板刺激的凝血。因此，由血小板激活或血小板聚集水平不当高导致的疾病或疾病可以通过给予一种治疗有效量的杂环化合物或非杂环线粒体抑制剂来治疗，该化合物显著降低了一个或多个血小板功能，包括凝聚、粘附或血小板刺激的凝血，最好是以可逆的方式。
• Post-synthetic modification of tryptophan containing peptides via NIS mediation
  作者：Chen-Xue Gu、Qing-Wei Bi、Chu-Kun Gao、Jian Wen、Zhi-Gang Zhao、Zili Chen

  DOI：10.1039/c7ob00329c

  日期：——

  A new efficient method was developed to provide modified tryptophan peptides through NIS (N-iodosuccinimide) mediated N2-selective coupling of a Trp unit with 1,2,3-triazoles, of which, the preliminary spectral properties were also studied.

  开发了一种新的有效方法，以通过NIS（N-碘琥珀酰亚胺）介导的Trp单元与1,2,3-三唑的N 2-选择性偶联提供修饰的色氨酸肽，还研究了其初步的光谱性质。
• Cyclin Based Inhibitors of CDK2 and CDK4
  申请人：McInnes Campbell

  公开号：US20130289240A1

  公开（公告）日：2013-10-31

  Structural and functional analysis of peptide inhibitor binding to the cyclin D and cyclin A groove has been investigated and used to design peptides that provide the basis for structure-activity relationships, have improved binding and have potential for development as chemical biology probes, as potential diagnostics and as therapeutics in the treatment of proliferative diseases including cancer and inflammation.

  研究了肽抑制剂与环D和环A凹槽的结构和功能分析，并用于设计肽，为结构活性关系提供基础，改善结合并具有作为化学生物学探针、潜在诊断和治疗增殖性疾病（包括癌症和炎症）的潜力。
• An FeCl₃-catalyzed three-component reaction for the synthesis of β-(1,2,3-triazolyl)-ketones using DMF as a one-carbon source
  作者：Ruilin Fang、Lei Zheng、Xuyang Chen、Can Wang、Yunfeng Chen

  DOI：10.1039/d4ob00207e

  日期：——

  An FeCl3-catalyzed oxidative condensation of NH-1,2,3-triazoles, aryl methyl ketones (or acetophenones) and DMF (N,N-dimethylformamide) for the synthesis of β-(1,2,3-triazolyl)-ketones was developed. DMF serves as a one-carbon source, and the resulting products display diverse reaction selectivity, highlighting the existence of distinct approaches.

  FeCl 3催化NH -1,2,3-三唑、芳基甲基酮（或苯乙酮）和 DMF（ N , N-二甲基甲酰胺）的氧化缩合，用于合成 β-(1,2,3-三唑基)-酮被开发出来。 DMF 作为单碳源，所得产物显示出不同的反应选择性，凸显了不同方法的存在。