4-(tert-butyl)phenyl 1H-imidazole-1-sulfonate

• 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: 4-(tert-butyl)phenyl 1H-imidazole-1-sulfonate
• 英文别名: 4-tert-butylphenyl 1H-imidazole-1-sulfonate；(4-Tert-butylphenyl) imidazole-1-sulfonate；(4-tert-butylphenyl) imidazole-1-sulfonate
• 化学式: C₁₃H₁₆N₂O₃S
• 分子量: 280.348
• InChiKey: ZEPNUILESIQLRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tert-butyl)phenyl 1H-imidazole-1-sulfonate 在 caesium carbonate 作用下， 以 乙醚 、 2,2,2-三氟乙醇 、 丙酮 为溶剂， 反应 26.0h， 生成 4-叔丁基联苯
  参考文献：
  名称：

  Aryl Imidazylates and Aryl Sulfates As Electrophiles in Metal-Free ArS_N1 Reactions

  摘要：

  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.

  DOI：

  10.1021/jo502172c
• 作为产物：
  描述：

  4-叔丁基苯酚 、 N,N-硫酰二咪唑 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以91%的产率得到4-(tert-butyl)phenyl 1H-imidazole-1-sulfonate
  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

文献信息

• O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release
  作者：Baocheng Yang、Zhexun Sun、Changzhi Liu、Yan Cui、Zhilei Guo、Yuwei Ren、Zhijian Lu、Spencer Knapp

  DOI：10.1016/j.tetlet.2014.10.065

  日期：2014.12

  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.
• 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.