1-(2,2,2-trichloroethoxysulfuryl)-2-isopropyl-3-methylimidazolium triflate | 1185733-74-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-(2,2,2-trichloroethoxysulfuryl)-2-isopropyl-3-methylimidazolium triflate
• 英文别名: 2,2,2-Trichloroethyl 3-methyl-2-propan-2-ylimidazol-3-ium-1-sulfonate;trifluoromethanesulfonate
• CAS: 1185733-74-7
• 化学式: CF₃O₃S*C₉H₁₄Cl₃N₂O₃S
• 分子量: 485.717
• InChiKey: LXAQVFNEPHTDHO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside 、 1-(2,2,2-trichloroethoxysulfuryl)-2-isopropyl-3-methylimidazolium triflate 在 1,2-二甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以66%的产率得到p-methoxyphenyl 2,3-di-O-acetyl-4-O-trichloroethylsulfo-6-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  O- and N-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts

  摘要：

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.

  DOI：

  10.1021/jo9014112
• 作为产物：
  描述：

  1-(2,2,2-trichloroethoxysulfuryl)-2-isopropylimidazole 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 以85%的产率得到1-(2,2,2-trichloroethoxysulfuryl)-2-isopropyl-3-methylimidazolium triflate
  参考文献：
  名称：

  O- and N-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts

  摘要：

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.

  DOI：

  10.1021/jo9014112

文献信息

• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.