1H,1H-trifluorethyl-chlorsulfat | 871-35-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1H,1H-trifluorethyl-chlorsulfat
• 英文别名: 2,2,2-Trifluorethylchlorosulfat；Schwefelsaeure-chlorid-(2,2,2-trifluor-ethylester)；Chlorsulfonsaeure-(2.2.2-trifluorethylester)；chlorosulfuric acid 2,2,2-trifluoro-ethyl ester；2-Chlorosulfonyloxy-1,1,1-trifluoroethane
• CAS: 871-35-2
• 化学式: C₂H₂ClF₃O₃S
• 分子量: 198.55
• InChiKey: XCDHDCRSARQIQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-甲基咪唑 、 1H,1H-trifluorethyl-chlorsulfat 以 四氢呋喃 为溶剂， 以87%的产率得到2,2,2-trifluoroethyl 2-methyl-1H-imidazole-1-sulfonate
  参考文献：
  名称：

  Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts

  摘要：

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.085
• 作为产物：
  描述：

  2,2,2-三氟乙醇钠 在 磺酰氯 作用下， 生成 1H,1H-trifluorethyl-chlorsulfat
  参考文献：
  名称：

  Nucleophilic Substitution in Fluoroalkyl Sulfates, Sulfonates, and Related Compounds

  摘要：

  DOI：

  10.1021/jo01068a091

文献信息

• 非対称イミド三級アンモニウム塩の製造方法
  申请人：セントラル硝子株式会社

  公开号：JP2018177670A

  公开（公告）日：2018-11-15

  【課題】対応するリン酸アミドと対応するスルホニルハライドより、選択率良く非対称イミド三級アンモニウム塩を製造する方法の提供。【解決手段】式（２）で示されるリン酸アミドと式（３）で示されるスルホニルハライドを、有機塩基の存在下で反応する、式（１）で示される非対称イミド三級アンモニウム塩の製造方法。［Ｒ１及びＲ２は夫々独立にハロゲン基、アルキル基、アルコキシ基等；式（３）のＲ２の少なくとも一つはハロゲン基；Ｒ３は、トリメチルシリル基又はＨ；ｎは１又は２；Ｍ１ ｎ＋は、三級アンモニウムカチオン］【選択図】図１

  提供一种制备高选择性制造非对称亚磷酸酰胺三级铵盐的方法，该方法是通过在有机碱的存在下使式（2）中所示的亚磷酸酰胺与式（3）中所示的磺酰氯反应来制备式（1）中所示的非对称亚磷酸酰胺三级铵盐。【R1和R2各自独立地是卤素基、烷基、烷氧基等；式（3）中的R2至少一个是卤素基；R3是三甲基硅基或H；n为1或2；M1 n+为三级铵阳离子】。
• Charalambous,J. et al., Journal of the Chemical Society, 1964, p. 5480 - 5482
  作者：Charalambous,J. et al.

  DOI：——

  日期：——
• Perhaloalkyl hypochlorites and pentafluorosulfur hypochlorite. II. Preparation of perfluoro-tert-butyl hypochlorite and related compounds
  作者：David Edward Young、Lowell Ray Anderson、Douglas E. Gould、William B. Fox

  DOI：10.1021/ja00711a019

  日期：1970.4
• CHATGILIALOGLU, C.;GRILLER, D.;ROSSINI, S., J. ORG. CHEM., 54,(1989) N1, C. 2734-2737
  作者：CHATGILIALOGLU, C.、GRILLER, D.、ROSSINI, S.

  DOI：——

  日期：——
• Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts
  作者：Ahmed Y. Desoky、Jennifer Hendel、Laura Ingram、Scott Douglas Taylor

  DOI：10.1016/j.tet.2010.11.085

  日期：2011.2

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.