[(3R,4R,5S,6R)-4,5-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate | 1430089-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3R,4R,5S,6R)-4,5-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 1430089-24-9
• 化学式: C₁₃H₁₆Cl₃NO₈
• 分子量: 420.631
• InChiKey: NAGHJYXWJQCCPK-CHWFTXMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3R,4R,5S,6R)-4,5-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate 、 N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-[(trifluoromethyl)-sulfinyl]-1H-pyrazol-5-yl]-aminoethanol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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

文献信息

• Synthesis of Rotenone-<i>O</i>-monosaccharide Derivatives and Their Phloem Mobility
  作者：Pei-Wen Qin、Jie Wang、Hao Wang、Ying-Jie Wen、Meng-Ling Lu、Yu-Feng Li、Yue-Shuo Xu、Han-Hong Xu

  DOI：10.1021/jf500197k

  日期：2014.5.21

  Six monosaccharide derivatives of rotenone were designed and synthesized to assess whether rotenone could become phloem mobile by the addition of a monosaccharide group. Phloem mobility experiments showed that only D-glucose conjugates exhibit phloem transport properties in castor bean (Ricinus communis L.) seedlings. Two D-glucose conjugates, 2-O-beta-D-glucopyranosyldemethylrotenone and 6'-O-beta-D-glucopyranosyldalpanol, had significantly obtained systemicity compared with that of rotenone, and 6'-O-beta-D-glucopyranosyldalpanol was more mobile than 2-O-beta-D-glucopyranosyldemethylrotenone. Coupling with a monosaccharide core is a reasonable method for conferring phloem mobility on insecticides, but phloem mobility is also affected by the parent molecule and the position of the monosaccharide.