2-(2-chloroethoxy)ethyl trifluoromethanesulfonate | 132539-93-6

• 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: 2-(2-chloroethoxy)ethyl trifluoromethanesulfonate
• 英文别名: 2-(2-chloroethoxy)ethyl triflate
• CAS: 132539-93-6
• 化学式: C₅H₈ClF₃O₄S
• 分子量: 256.63
• InChiKey: QPDWTPUTDDACOR-UHFFFAOYSA-N

物化性质

• 沸点：
  248.3±40.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-<(hydroxyimino)methyl>-1-methylimidazole 、 2-(2-chloroethoxy)ethyl trifluoromethanesulfonate 以76%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 、 2-氯乙氧基乙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-(2-chloroethoxy)ethyl trifluoromethanesulfonate
  参考文献：
  名称：

  具有冠醚状结构的大环手性磷烷衍生物的合成方法

  摘要：

  (S,S)-双（2-羟丙基）（苯基）氧化膦，通过（S）-氧化丙烯与二锂（苯基）膦的开环或双（2-氧丙基）催化氢化制备(苯基)氧化膦，由钌/MeO-BIPHEP促进。催化氢化还允许从相应的二酮对映选择性合成（R，R）-双（2-苯基-2-羟乙基）（苯基）氧化膦。这些双（β-羟烷基）膦衍生物是合成 1-phospha-10-aza-18-crown-6 衍生物的合适手性原料，这是光学纯、冠醚类、含磷大环的第一个例子. 其中之一已通过 X 射线衍射研究进行了表征。已通过 1 H NMR 分析观察到 Na+ 与大环的冠醚部分发生络合。(© Wiley-VCH Verlag GmbH & Co.

  DOI：

  10.1002/ejoc.200500455

文献信息

• Deconstructing Best‐in‐Class Neoglycoclusters as a Tool for Dissecting Key Multivalent Processes in Glycosidase Inhibition
  作者：Yan Liang、Rosaria Schettini、Nicolas Kern、Luca Manciocchi、Irene Izzo、Martin Spichty、Anne Bodlenner、Philippe Compain

  DOI：10.1002/chem.202304126

  日期：2024.4.2

  deconstruction of best-in-class multivalent inhibitors shed new lights on the contribution of chelation and statistical rebinding mechanisms underlying high multivalent effect in glycosidase inhibition. This experimental–theoretical approach provides insights from various dimensions (statistical, stoichiometric, electrostatics) and relevant guidelines for the design of optimized multivalent enzyme inhibitors.

  解构理解：基于对一流多价抑制剂自上而下解构的结构-活性关系研究，为糖苷酶抑制中高多价效应背后的螯合和统计重结合机制的贡献提供了新的线索。这种实验理论方法为优化多价酶抑制剂的设计提供了来自各个维度（统计、化学计量、静电）的见解和相关指南。
• 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.