N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine | 1349710-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine
• 英文别名: 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)-5-[[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methylamino]pyrazole-3-carbonitrile
• CAS: 1349710-03-7
• 化学式: C₂₁H₁₇Cl₂F₆N₇O₆S
• 分子量: 680.372
• InChiKey: LRKLXTAYSOAJNQ-QXRLNHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  211
• 氢给体数：
  5
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 copper(ll) sulfate pentahydrate 、 水 、 sodium methylate 、 sodium ascorbate 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 3.5h， 生成 N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine
  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

文献信息

• Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates
  作者：Zhiwei Lei、Jie Wang、Genlin Mao、Yingjie Wen、Yuxin Tian、Huawei Wu、Yufeng Li、Hanhong Xu

  DOI：10.1021/jf5010429

  日期：2014.7.2

  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.