hex-5-yn-1-yl trifluoromethanesulfonate | 85355-21-1

• 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: hex-5-yn-1-yl trifluoromethanesulfonate
• 英文别名: Hex-5-ynyl trifluoromethanesulfonate；hex-5-ynyl trifluoromethanesulfonate
• CAS: 85355-21-1
• 化学式: C₇H₉F₃O₃S
• 分子量: 230.208
• InChiKey: YNQLSCZOKZANKN-UHFFFAOYSA-N

物化性质

• 沸点：
  223.1±40.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  hex-5-yn-1-yl trifluoromethanesulfonate 在 盐酸羟胺 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 1-(hex-5'-yn-1'-yl)-2-<(hydroxyimino)methyl>imidazole
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication

  摘要：

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.

  DOI：

  10.1021/jm00122a035
• 作为产物：
  描述：

  5-己炔-1-醇 、 三氟甲磺酸酐 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 hex-5-yn-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  磷-奥司他韦的生物素，荧光素和“可点击”偶联物作为流感病毒的探针，利用对神经氨酸酶的选择性结合†

  摘要：

  磷酸-奥司他韦与已建立的报告基团荧光素和生物素的缀合物的合成，并描述了一种多聚体抑制剂的方法。我们报告了由这些探针对流感神经氨酸酶的强力抑制作用，并通过与神经氨酸酶滴定定量了荧光素结合物的结合过程中的荧光猝灭。因此，我们表明它们可能是有效抑制，检测和定量生物系统中病毒和神经氨酸酶的有用工具。

  DOI：

  10.1039/c1ob05384a

文献信息

• Reversal of Tabun Toxicity Enabled by a Triazole‐Annulated Oxime Library—Reactivators of Acetylcholinesterase
  作者：Zrinka Kovarik、Jarosław Kalisiak、Nikolina Maček Hrvat、Maja Katalinić、Tamara Zorbaz、Suzana Žunec、Carol Green、Zoran Radić、Valery V. Fokin、K. Barry Sharpless、Palmer Taylor

  DOI：10.1002/chem.201805051

  日期：2019.3.15

  and for post‐exposure treatment is a continued challenge. In this study, we analyzed the reactivation potency of 111 novel nucleophilic oximes mostly synthesized using the CuAAC triazole ligation between alkyne and azide building blocks. We identified several oximes with significantly improved in vitro reactivating potential for tabun‐inhibited human AChE, and in vivo antidotal efficacies in tabun‐exposed

  乙酰胆碱酯酶（AChE）是一种降解神经递质乙酰胆碱的酶，当被有机磷化合物（OPs）（例如神经毒剂和杀虫剂）共价抑制时，可以被肟重新激活。然而，由于标准吡啶鎓醛肟肟解毒剂的低活化作用，塔邦仍然是最危险的神经制剂之一。因此，寻找最佳的活化剂来预防塔宾毒性和进行暴露后治疗仍然是一个挑战。在这项研究中，我们分析了炔烃和叠氮化物结构单元之间主要通过CuAAC三唑连接而合成的111种新型亲核肟的活化潜能。我们鉴定了几种肟，它们在禁忌暴露的人AChE中具有显着提高的体外再激活潜力，并且在禁忌暴露的小鼠中具有体内解毒作用。
• [EN] RAPAMYCIN ANALOGS AS MTOR INHIBITORS<br/>[FR] ANALOGUES DE LA RAPAMYCINE UTILISÉS EN TANT QU'INHIBITEURS DE MTOR
  申请人：REVOLUTION MEDICINES INC

  公开号：WO2018204416A1

  公开（公告）日：2018-11-08

  The present disclosure relates to rapamycin analogs of the general Formula (I). The compounds are inhibitors of mTOR and thus useful for the treatment of cancer, immune-mediated diseases and age related conditions.

  本公开涉及一般式（I）的雷帕霉素类似物。这些化合物是mTOR的抑制剂，因此对于治疗癌症、免疫介导性疾病和与年龄相关的疾病是有用的。
• A Chiral Dicationic [8]Circulenoid: Photochemical Origin and Facile Thermal Conversion into a Helicene Congener
  作者：Lukáš Severa、Milan Ončák、Dušan Koval、Radek Pohl、David Šaman、Ivana Císařová、Paul E. Reyes-Gutiérrez、Petra Sázelová、Václav Kašička、Filip Teplý、Petr Slavíček

  DOI：10.1002/anie.201203562

  日期：2012.11.26

  Doubly positive: A circulene‐like species has been transformed into its helical counterpart exclusively by the application of heat (see scheme). The synthesis of the chiral dicationic [8]circulenoid is based on a key [6+6] photocycloaddition and requires only five steps and no chromatographic purification.

  双重正值：仅通过加热即可将类似circulene的物种转化为其螺旋对应物（请参见方案）。手性双键[8]环状分子的合成基于关键的[6 + 6]光环加成反应，仅需五个步骤，无需色谱纯化。
• Function-based probes for environmental microbiome analysis and methods of making and using the same
  申请人：Battelle Memorial Institute

  公开号：US11169152B2

  公开（公告）日：2021-11-09

  Probe embodiments for identifying analytes involved in biofuel or bioenergy production, bioremediation, or nutrient cycling as well as methods of making and use are described herein. In some embodiments, probes identifying cellulose degradation and/or sugar transport, lignin or chitin degradation, or peptide or toxin metabolism are included. In some embodiments, probes for identifying analytes in a soil sample are included in the compositions and methods disclosed herein.

  本文描述了用于鉴定涉及生物燃料或生物能源生产、生物修复或营养循环的分析物的探针实施方案以及制造和使用方法。在某些实施方案中，包括用于鉴定纤维素降解和/或糖转运、木质素或几丁质降解或肽或毒素代谢的探针。在某些实施方案中，用于鉴定土壤样本中分析物的探针也包含在本文公开的组合物和方法中。
• Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization
  作者：Lukáš Severa、Louis Adriaenssens、Jan Vávra、David Šaman、Ivana Císařová、Pavel Fiedler、Filip Teplý

  DOI：10.1016/j.tet.2010.03.007

  日期：2010.5

  A protocol for rapid and highly modular assembly of a diverse set of helquats is described. From a common bis-isoquinoline precursor, two successive distinct pyridine-type nitrogen quaternizations followed by rhodium-catalyzed [2+2+2] cycloaddition afford non-symmetric [7]helquats. This route allows for straightforward molecular editing of cationic helical skeletons as exemplified by the synthesis of 15 different [5]-, [6]-, and [7]helquats. (C) 2010 Elsevier Ltd. All rights reserved.