1-(4-methymercaptophenoxysulfuryl)imidazole | 1269657-74-0

• 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: 1-(4-methymercaptophenoxysulfuryl)imidazole
• CAS: 1269657-74-0
• 化学式: C₁₀H₁₀N₂O₃S₂
• 分子量: 270.333
• InChiKey: BPFMHJQSSMUXLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.19
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(4-methymercaptophenoxysulfuryl)imidazole 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 3.5h， 以86%的产率得到3-methyl-1-((4-(methylthio)phenoxy)sulfonyl)-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
• 作为产物：
  描述：

  4-(甲硫基)苯酚 、 N,N-硫酰二咪唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以67%的产率得到1-(4-methymercaptophenoxysulfuryl)imidazole
  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

• Palladium-Catalyzed Cyanations of Aryl Imidazolylsulfonates with K4[Fe(CN)6]: A Pragmatic Approach to Benzonitriles from Phenols
  作者：Jennifer Albaneze-Walker、Doug E. Frantz、Nicolas A. Wilson、William M. Palmer、Jacob M. Ganley、John R. Coombs、Mark S. Levorse

  DOI：10.1055/a-2331-2707

  日期：2024.9

  conversion of phenols into benzonitriles via aryl imidazolylsulfonates with a non-toxic cyanide source, potassium ferrocyanide, has been developed. Salient features of this method include low palladium precatalyst loadings (as low as 1.0 mol% total Pd), mild reaction conditions, and environmentally benign by-products compared to other (pseudo)halide aryl electrophiles. The initial scope of the reaction

  已经开发出一种通用的钯催化方法，通过芳基咪唑基磺酸盐与无毒的氰化物源亚铁氰化钾将苯酚转化为苯酚。与其他（拟）卤化芳基亲电子试剂相比，该方法的显着特点包括钯预催化剂负载量低（总钯含量低至 1.0 mol%）、温和的反应条件以及对环境无害的副产物。演示了一系列酚类前体反应的初始范围，包括将酚直接转化为苯甲腈的一锅两步方法。