2-甲氧基苯基1H-咪唑-1-磺酸盐 | 1207429-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-甲氧基苯基1H-咪唑-1-磺酸盐
• 英文名称: 2-methoxyphenyl 1H-imidazole-1-sulfonate
• 英文别名: (2-Methoxyphenyl) imidazole-1-sulfonate；(2-methoxyphenyl) imidazole-1-sulfonate
• CAS: 1207429-55-7
• 化学式: C₁₀H₁₀N₂O₄S
• 分子量: 254.266
• InChiKey: SBZLYHOJFNDBOL-UHFFFAOYSA-N

物化性质

• 沸点：
  441.9±47.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲氧基苯基1H-咪唑-1-磺酸盐 以 二氯甲烷 、 乙腈 为溶剂， 生成 Diaethylaminosulfonsaeure-(2-methoxy-phenyl)-ester
  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：

  木榴油 、 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98%的产率得到2-甲氧基苯基1H-咪唑-1-磺酸盐
  参考文献：
  名称：

  通过亲核放射性氟化合成18 F标记的芳基氟代硫酸盐。

  摘要：

  硫酰氟气体是SO 2 F转移的关键试剂。然而，由于无法获得气态[ 18 F] SO 2 F 2，传统的SO 2 F转移反应具有局限性的18 F-放射化学转化。在此，我们报告了使用回旋加速器生产的18 F –酚和分离的芳基亚氨基磺酸酯前体，首次合成无SO 2 F 2的芳基[ 18 F]氟代硫酸盐–。放射化学收率范围从中等到良好，且具有出色的官能团耐受性。我们的方法的可靠性通过4-乙酰氨基苯基[ 18 F]氟硫酸盐的自动放射合成得到了验证。

  DOI：

  10.1021/acs.orglett.0c01868

文献信息

• Palladium-Catalyzed Mono-α-Arylation of Acetone with Aryl Imidazolylsulfonates
  作者：Lutz Ackermann、Vaibhav P. Mehta

  DOI：10.1002/chem.201201394

  日期：2012.8.13

  Set the ace(tone): A palladium catalyst derived from the bidentate XantPhos ligand and Pd(OAc)2 has enabled broadly applicable mono‐α‐arylations of acetone to be performed with air‐ and moisture‐stable aryl imidazolylsulfonates as most user‐friendly electrophiles (see scheme).

  设定ace（tone）：一种由双齿XantPhos配体和Pd（OAc）2衍生的钯催化剂，使得最广泛使用的丙酮单α-芳基化反应可以与空气和水分稳定的芳基咪唑基磺酸盐一起使用，这是最易于使用的亲电试剂（请参阅方案）。
• Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C−H Bond Cleavages with Sulfamates or Phosphates as Electrophiles
  作者：Lutz Ackermann、Sebastian Barfüsser、Jola Pospech

  DOI：10.1021/ol9028034

  日期：2010.2.19

  A catalytic system comprised of Pd(OAc)2 and bidentate ligand dppe enabled first direct arylations with moisture-stable aryl sulfamates as electrophiles, and proved applicable to unprecedented C−H bond functionalizations with easily accessible alkenyl phosphates as well as benzyl phosphates.

  由Pd（OAc）2和二齿配体dppe组成的催化体系能够首先将湿气稳定的芳基氨基磺酸盐作为亲电子试剂进行直接芳基化反应，并证明适用于空前的C-H键官能化，且易于获得的烯基磷酸酯和磷酸苄酯。
• Catalytic constructive deoxygenation of lignin-derived phenols: new C–C bond formation processes from imidazole-sulfonates and ether cleavage reactions
  作者：Stuart M. Leckie、Gavin J. Harkness、Matthew L. Clarke

  DOI：10.1039/c4cc04939j

  日期：——

  feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

  作为旨在利用木质素作为含氧量较小的精细化学品的化学原料的计划的一部分，展示了几种利用愈创木酚咪唑磺酸盐的催化CC键形成反应。这些包括格利雅（Grignard），无毒氰化物源，苯并恶唑和硝基甲烷的交叉偶联。改良的Meyers反应用于在苯并恶唑官能化的茴香醚上进行第二次结构性脱氧。
• 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.
• Synthesis of ¹⁸F-Labeled Aryl Fluorosulfates via Nucleophilic Radiofluorination
  作者：Young-Do Kwon、Min Ho Jeon、Nam Kyu Park、Jeong Kon Seo、Jeongmin Son、Young Hoon Ryu、Sung You Hong、Joong-Hyun Chun

  DOI：10.1021/acs.orglett.0c01868

  日期：2020.7.17

  first SO2F2-free synthesis of aryl [18F]fluorosulfates from both phenolic and isolated aryl imidazylate precursors with cyclotron-produced 18F–. The radiochemical yields ranged from moderate to good with excellent functional group tolerance. The reliability of our approach was validated by the automated radiosynthesis of 4-acetamidophenyl [18F]fluorosulfate.

  硫酰氟气体是SO 2 F转移的关键试剂。然而，由于无法获得气态[ 18 F] SO 2 F 2，传统的SO 2 F转移反应具有局限性的18 F-放射化学转化。在此，我们报告了使用回旋加速器生产的18 F –酚和分离的芳基亚氨基磺酸酯前体，首次合成无SO 2 F 2的芳基[ 18 F]氟代硫酸盐–。放射化学收率范围从中等到良好，且具有出色的官能团耐受性。我们的方法的可靠性通过4-乙酰氨基苯基[ 18 F]氟硫酸盐的自动放射合成得到了验证。