(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazol-5-yl)amino)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1430089-26-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazol-5-yl)amino)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1430089-26-1
• 化学式: C₂₈H₂₆Cl₂F₆N₄O₁₁S
• 分子量: 811.497
• InChiKey: IHGWJBYBADSIJV-CNTAKPGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  52.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  194.37
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazol-5-yl)amino)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)-sulfinyl]-1H-pyrazol-5-yl]-2-aminoethyl β-D-glucopyranoside 、 N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)-sulfinyl]-1H-pyrazol-5-yl]-2-aminoethyl α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Series of Monosaccharide–Fipronil Conjugates and Their Phloem Mobility

  摘要：

  To test the effect of adding different monosaccharide groups to a non-phloem-mobile insecticide on the phloem mobility of the insecticide, a series of conjugates of different monosaccharides and fipronil were synthesized using the trichloroacetimidate method. Phloem mobility tests in castor bean (Ricinus communis L.) seedlings indicated that the phloem mobility of these conjugates varied markedly. L-Rhamnose fipronil and D-fucose fipronil displayed the highest phloem mobility among all of the tested conjugates. Conjugating hexose, pentose, or deoxysugar to fipronil through an O-glycosidic linkage can confer phloem mobility to fipronil in R. communis L. effectively, while the -OH orientation of the monosaccharide substantially affected the phloem mobility of the conjugates.

  DOI：

  10.1021/jf400888c
• 作为产物：
  描述：

  ethyl N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-[(trifluoromethyl)-sulfinyl]-1H-pyrazol-5-yl]-aminoacetate 在 sodium tetrahydroborate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazol-5-yl)amino)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of a Series of Monosaccharide–Fipronil Conjugates and Their Phloem Mobility

  摘要：

  To test the effect of adding different monosaccharide groups to a non-phloem-mobile insecticide on the phloem mobility of the insecticide, a series of conjugates of different monosaccharides and fipronil were synthesized using the trichloroacetimidate method. Phloem mobility tests in castor bean (Ricinus communis L.) seedlings indicated that the phloem mobility of these conjugates varied markedly. L-Rhamnose fipronil and D-fucose fipronil displayed the highest phloem mobility among all of the tested conjugates. Conjugating hexose, pentose, or deoxysugar to fipronil through an O-glycosidic linkage can confer phloem mobility to fipronil in R. communis L. effectively, while the -OH orientation of the monosaccharide substantially affected the phloem mobility of the conjugates.

  DOI：

  10.1021/jf400888c