1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-(prop-2-yn-1-ylamino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile | 1192822-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-(prop-2-yn-1-ylamino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile
• 英文别名: 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(prop-2-ynylamino)-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
• CAS: 1192822-71-1
• 化学式: C₁₅H₆Cl₂F₆N₄OS
• 分子量: 475.201
• InChiKey: XANKYMVLQHVMKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-azido-4-deoxy-α-D-glucopyranose 、 1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-(prop-2-yn-1-ylamino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile 在 copper(ll) sulfate pentahydrate 、 水 、 sodium ascorbate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 生成 C₂₉H₂₅Cl₂F₆N₇O₁₀S
  参考文献：
  名称：

  Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates

  摘要：

  In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

  DOI：

  10.1021/jf5010429
• 作为产物：
  描述：

  3-溴丙炔 、 氟虫腈 在 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以50%的产率得到1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-(prop-2-yn-1-ylamino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile
  参考文献：
  名称：

  荧光灯-氟吡尼：稳定共轭物的设计与合成

  摘要：

  Fipronil是一种苯基吡唑分子，在世界范围内广泛用作杀虫剂和兽药。这项工作的主要目的是合成一种荧光标记的氟虫腈衍生物用于细胞成像，而不会影响其内在特性。我们选择荧光素作为荧光探针，我们研究了在两个实体之间进行稳定化学连接的不同策略，例如硫脲和直接肽键。尽管硫脲键显示出低稳定性，但是由于空间位阻的问题，难以实现直接肽键。通过使用点击化学的缀合获得最佳结果，这允许获得被荧光探针稳定标记的氟虫腈。

  DOI：

  10.1016/j.bmcl.2018.06.036

文献信息

• Synthesis and application of clickable and biocompatible fluorescent glycosyl labels
  作者：Zhiwei Lei、Jie Wang、Yuxin Tian、Gaopeng Song、Gang Zhao、Hanhong Xu

  DOI：10.1016/j.dyepig.2014.09.037

  日期：2015.2

  Two novel, biocompatible and highly stereoselective fluorescent glycosyl labels featuring azide groups have been successfully synthesized. The functional groups provide convenient routes for fluorescent glycosyl conjugates via click chemistry. Three fluorescent glycose-conjugates were synthesized. One fluorescent conjugate was used to trace the translocation in castor seedlings. The developed fluorescent labels for biomolecules are likely to provide an important method for investigating various biological events. We believe that the probes obtained are useful for studies on biological processes. (C) 2014 Elsevier Ltd. All rights reserved.