3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium trifluoromethanesulfonate | 1269657-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium trifluoromethanesulfonate
• 英文别名: 3-Methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium triflate；phenyl 3-methylimidazol-3-ium-1-sulfonate;trifluoromethanesulfonate
• CAS: 1269657-62-6
• 化学式: CF₃O₃S*C₁₀H₁₁N₂O₃S
• 分子量: 388.345
• InChiKey: IAVOZLBYGUEEIZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium trifluoromethanesulfonate 、 苯胺 以 乙腈 为溶剂， 生成 phenyl N-phenylsulfamate
  参考文献：
  名称：

  O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release

  摘要：

  Sequential replacement of imidazole from sulfonyldiimidazole by phenols and then amines leads to O-arylsulfamate esters. Application of this coupling method to 19 phenols and 6 amines generates a library of 114 sulfamate esters, Ar-OSO2-NR2. A sulfamate based conjugate of ethinyl estradiol was prepared by using the steroid 3-hydroxyl as the phenol component, and an amino amide derived from linoleic acid as the amine. Hydrolysis of this conjugate was studied in aqueous buffer at pH values 2, 5, and 7.4, and (essentially identical) respective half-lives of 6.8, 6.6, and 6.7 days were observed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.065
• 作为产物：
  描述：

  phenylchlorosulfate 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium trifluoromethanesulfonate
  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

文献信息

• Aryl sulfamide and sulfamate derivatives as RORc modulators
  申请人：Genentech, Inc.

  公开号：US08912219B2

  公开（公告）日：2014-12-16

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, p, q, r, A, X1, X2, X3, X4, X5, X6, Y, Z, G, R1a, R2a, R1b, R2b, R3, R4, R5 and R6 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of inflammatory diseases such as arthritis.

  公式I的化合物或其药学上可接受的盐，其中m，n，p，q，r，A，X1，X2，X3，X4，X5，X6，Y，Z，G，R1a，R2a，R1b，R2b，R3，R4，R5和R6的定义如本文所述。还揭示了制备该化合物的方法，并将该化合物用于治疗炎症性疾病，如关节炎。
• Aryl Imidazylates and Aryl Sulfates As Electrophiles in Metal-Free ArS_N1 Reactions
  作者：Hisham Qrareya、Stefano Protti、Maurizio Fagnoni

  DOI：10.1021/jo502172c

  日期：2014.12.5

  Some oxygen-bonded substituents were investigated as leaving groups in photoinduced ArSN1 reactions. Irradiation of aryl imidazylates and of the corresponding imidazolium salts mainly caused homolysis of the ArO-S bond. However, previously unexplored trifluoroethoxy aryl sulfates were found to undergo efficient metal-free arylation. The sulfates were conveniently generated in situ by dissolving the corresponding imidazolium salts in basic 2,2,2-trifluoroethanol.
• US20140275032A1
  申请人：——

  公开号：——

  公开（公告）日：——
• ARYL SULFAMIDE AND SULFAMATE DERIVATIVES AS RORc MODULATORS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2970116A1

  公开（公告）日：2016-01-20
• US8912219B2
  申请人：——

  公开号：US8912219B2

  公开（公告）日：2014-12-16