苯基1H-咪唑-1-磺酸盐 | 1198183-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯基1H-咪唑-1-磺酸盐
• 英文名称: phenyl 1H-imidazole-1-sulfonate
• 英文别名: Phenyl 1H-imidazole-1-sulfonate；phenyl imidazole-1-sulfonate
• CAS: 1198183-95-7
• 化学式: C₉H₈N₂O₃S
• 分子量: 224.24
• InChiKey: NTKIVUNQWDCFDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  苯基1H-咪唑-1-磺酸盐 在 1,2-二甲基咪唑 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 phenyl [(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl sulfate
  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：

  N,N-硫酰二咪唑 、 苯酚 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到苯基1H-咪唑-1-磺酸盐
  参考文献：
  名称：

  微波促进水中芳基咪唑基磺酸盐的无铜Sonogashira–gi原偶联反应

  摘要：

  在110℃无铜条件下，微波辐射辅助下，纯净水中的芳基咪唑-1-基磺酸盐已与芳基，烷基和甲硅烷基乙炔有效地交叉偶联。使用0.5摩尔％的肟四氮杂环丙烷作为前催化剂，使用2-二环己基膦基2'，6'-二甲氧基联苯（SPhos，2摩尔％）作为配体，十六烷基三甲基溴化铵（CTAB）作为添加剂，并使用三乙胺（TEA）作为碱仅30分钟就可以制备出高至高收率的双取代炔烃阵列。

  DOI：

  10.1002/adsc.201200629

文献信息

• Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates
  作者：Lutz Ackermann、René Sandmann、Weifeng Song

  DOI：10.1021/ol200267b

  日期：2011.4.1

  A nickel complex derived from dppf, along with NaOt-Bu as the base, allowed for challenging aminations of aryl sulfamates. An improved functional group tolerance is observed in novel palladium-catalyzed aminations of imidazolylsulfonates with rac-BINAP as the ligand.

  衍生自dppf的镍络合物以及NaO t -Bu作为碱，可实现富挑战性的氨基磺酸氨基酯的胺化反应。以rac -BINAP为配体的新型钯催化的咪唑基磺酸盐胺化反应观察到官能团耐受性提高。
• 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。
• Phosphane-free Suzuki–Miyaura Coupling of Aryl Imidazolesulfonates with Arylboronic Acids and Potassium Aryltrifluoroborates under Aqueous Conditions
  作者：José Francisco Cívicos、Mohammad Gholinejad、Diego A. Alonso、Carmen Nájera

  DOI：10.1246/cl.2011.907

  日期：2011.9.5

  Aryl imidazole-1-sulfonates are efficiently cross-coupled with arylboronic acids and potassium aryltrifluoroborates using only 0.5 mol % of oxime palladacycles 1 under aqueous conditions at 110 °C. Under these simple phosphane-free reaction conditions a wide array of biaryl derivatives has been prepared in high yields. This methodology allows in situ phenol sulfonation and one-pot Suzuki arylation as well as the employment of microwave irradiation conditions.

  基于水相条件、温度110°C下，仅使用0.5摩尔%的肟基钯杂环1，就能高效地实现芳基咪唑-1-磺酸盐与芳基硼酸及芳基三氟硼酸盐的交叉偶联。在这些简单的无膦反应条件下，大量的联苯衍生物已经以高产率制备完成。该方法学能够实现酚羟基的定向磺化、一步Suzuki偶联反应以及利用微波辐照条件。
• Oxime-Palladacycle-Catalyzed Suzuki-Miyaura Arylation and Alkenylation of Aryl Imidazolesulfonates under Aqueous and Phosphane-Free Conditions
  作者：José Francisco Cívicos、Diego A. Alonso、Carmen Nájera

  DOI：10.1002/ejoc.201200368

  日期：2012.7

  Aryl and hetaroaryl imidazole-1-sulfonates are efficiently arylated and alkenylated with aryl- and alkenylboronic acids and potassium trifluoroborates by using 0.5 mol-% palladacycles 1 or Pd(OAc)2 at 110 °C under aqueous and phosphane-free conditions. Reactions can be performed by using conventional or microwave heating, leading to biaryls, stilbenes, and alkenylarenes in good to high yields, and

  芳基和杂芳基咪唑-1-磺酸盐通过使用 0.5 mol% 钯环 1 或 Pd(OAc)2 在 110 °C 下，在水性和无磷烷条件下，被芳基和烯基硼酸以及三氟硼酸钾有效地芳基化和烯基化。反应可以通过使用常规或微波加热进行，从而以良好到高产率以及高区域选择性和非对映选择性产生联芳烃、芪和烯基芳烃。优化的方法允许原位苯酚磺酰化和一锅 Suzuki 芳基化或烯基化以及含卤素芳基咪唑磺酸盐的正交功能化。