Trifluoro-methanesulfonic acid 2-cyano-ethyl ester | 132539-88-9

• 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: Trifluoro-methanesulfonic acid 2-cyano-ethyl ester
• 英文别名: 2-Cyanoethyl trifluoromethanesulfonate
• CAS: 132539-88-9
• 化学式: C₄H₄F₃NO₃S
• 分子量: 203.142
• InChiKey: SMEUIZSCHUEFOC-UHFFFAOYSA-N

物化性质

• 沸点：
  234.3±40.0 °C(Predicted)
• 密度：
  1.542±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-<(hydroxyimino)methyl>-1-methylimidazole 、 Trifluoro-methanesulfonic acid 2-cyano-ethyl ester 以67%的产率得到
  参考文献：
  名称：

  GOFF, DANE A.;KOOLPE, GARY A.;KELSON, ANDREW B.;VU, HUYNH M.;TAYLOR, DORR+, J. MED. CHEM., 34,(1991) N, C. 1363-1366

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟甲磺酸酐 、 3-羟基丙腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Trifluoro-methanesulfonic acid 2-cyano-ethyl ester
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 4. Effect of various side-chain substituents on therapeutic activity against anticholinesterase intoxication

  摘要：

  A series of quaternary salt derivatives of 2-[(hydroxyimino)methyl]-1-methylimidazole incorporating various side chains bearing ether, silyl, nitrile, ester, halogen, nitro, sulfone, amino, or aminosulfonyl substituents was prepared and evaluated in vivo for the treatment of anticholinesterase intoxication. Test results in the mouse revealed that the type and location of the side-chain substituent both have a significant influence on the toxicity and antidotal effectiveness of the compounds. Some of the more active examples represent the most potent therapeutics to date against intoxication by the powerful cholinesterase inhibitors soman and tabun. Significantly, the antidotal effectiveness of the compounds was not dependent on the inhibiting agent nor was there any correlation between in vivo efficacy and in vitro reactivation of ethyl (4-nitrophenyl)methylphosphonate inhibited human acetylcholinesterase. These observations suggested that the main mode of antidotal protection by the compounds is something other than enzyme reactivation.

  DOI：

  10.1021/jm00108a019

文献信息

• 10.1002/adsc.202400510
  作者：Paut, Julien、Baldon, Simone、Anselmi, Elsa、Dell'Amico, Luca、Dagousset, Guillaume、Magnier, Emmanuel

  DOI：10.1002/adsc.202400510

  日期：——

  excess of alcohol (40–120 equiv.) to reach high efficiency, which can hamper its application in the case of more complex alcohols (Scheme 1b).5 Very recently, complementary approaches involving O-centered radicals were independently developed by Zhu, Yang et al.6 and by Cheong, Altman et al.7 Although performant, these strategies were limited to phenoxy groups (R=Ar, Scheme 1c). Scheme 1 Open in figure

   介绍 由于氟原子对化学品的物理和生物性质的独特影响，有机氟化学在各个领域发挥着核心作用，在材料、农业化学和医学科学方面有许多应用。 1值得注意的是，α-氟烷基醚，特别是三氟甲基醚和二氟甲基醚（分别为 Y=F 和 Y=H，方案 1a）最近引起了越来越多的关注。 2开发有效的方案来制备这些分子很可能是现在在众多生物相关化合物中发现它们的原因。 2相比之下，尽管人们对更多功能化的二氟甲氧基单元的潜在兴趣很高，但对它们的研究却少得多。可用的方法主要集中于醇盐（主要是酚盐）与溴二氟乙酸乙酯的亲电二氟甲基化（Y=CO 2 Et，方案1a）。 3然而，针对二氟烷氧基甲基酮 (Y=C(O)R 2 ) 的类似方法更具挑战性，因为以 O 为中心的亲核试剂可以添加到羰基上并释放二氟卡宾。 4 Len、Hu等人于 2023 年提出了这些化合物的替代途径。使用宝石二氟化富电子苯乙烯作为氟化结构单元。 5然而，该反应需要大量过量的醇（40-120
• GOFF, DANE A.;KOOLPE, GARY A.;KELSON, ANDREW B.;VU, HUYNH M.;TAYLOR, DORR+, J. MED. CHEM., 34,(1991) N, C. 1363-1366
  作者：GOFF, DANE A.、KOOLPE, GARY A.、KELSON, ANDREW B.、VU, HUYNH M.、TAYLOR, DORR+

  DOI：——

  日期：——
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 4. Effect of various side-chain substituents on therapeutic activity against anticholinesterase intoxication
  作者：Dane A. Goff、Gary A. Koolpe、Andrew B. Kelson、Huynh M. Vu、Dorris L. Taylor、Clifford D. Bedford、Ralph N. Harris、H. A. Mussalam、Irwin Koplovitz

  DOI：10.1021/jm00108a019

  日期：1991.4

  A series of quaternary salt derivatives of 2-[(hydroxyimino)methyl]-1-methylimidazole incorporating various side chains bearing ether, silyl, nitrile, ester, halogen, nitro, sulfone, amino, or aminosulfonyl substituents was prepared and evaluated in vivo for the treatment of anticholinesterase intoxication. Test results in the mouse revealed that the type and location of the side-chain substituent both have a significant influence on the toxicity and antidotal effectiveness of the compounds. Some of the more active examples represent the most potent therapeutics to date against intoxication by the powerful cholinesterase inhibitors soman and tabun. Significantly, the antidotal effectiveness of the compounds was not dependent on the inhibiting agent nor was there any correlation between in vivo efficacy and in vitro reactivation of ethyl (4-nitrophenyl)methylphosphonate inhibited human acetylcholinesterase. These observations suggested that the main mode of antidotal protection by the compounds is something other than enzyme reactivation.