4-nitrophenyl 1H-imidazole-1-sulfonate | 1232660-40-0

• 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: 4-nitrophenyl 1H-imidazole-1-sulfonate
• 英文别名: (4-Nitrophenyl) imidazole-1-sulfonate
• CAS: 1232660-40-0
• 化学式: C₉H₇N₃O₅S
• 分子量: 269.238
• InChiKey: LUNIWPQQQCETHA-UHFFFAOYSA-N

物化性质

• 沸点：
  496.9±47.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 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：
  115
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 1H-imidazole-1-sulfonate 以 二氯甲烷 、 乙腈 为溶剂， 生成
  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：

  对硝基苯酚 、 N,N-硫酰二咪唑 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 4-nitrophenyl 1H-imidazole-1-sulfonate
  参考文献：
  名称：

  微波促进水中芳基咪唑基磺酸盐的铃木-宫浦交叉偶联

  摘要：

  使用0.5 mol％的肟基丙二环1a，十六烷基三甲基溴化铵（CTAB）作为添加剂，在微波加热（40 W，110°C）下，于纯净水中将芳基咪唑-1-基磺酸盐与芳基钾和烯基三氟硼酸钾有效地交叉偶联。三乙胺为碱。在这些简单的无膦反应条件下，仅需30分钟即可制备出多种多样的联芳基，二苯乙烯和苯乙烯衍生物，并具有良好的高收率，并且具有较高的区域选择性和非对映选择性。

  DOI：

  10.1002/adsc.201200364

文献信息

• 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。
• Copper-free palladium-catalyzed Sonogashira and Hiyama cross-couplings using aryl imidazol-1-ylsulfonates
  作者：Steven J. Shirbin、Berin A. Boughton、Steven C. Zammit、Shannon D. Zanatta、Sebastian M. Marcuccio、Craig A. Hutton、Spencer J. Williams

  DOI：10.1016/j.tetlet.2010.03.110

  日期：2010.6

  Aryl imidazylates are effective electrophilic partners in copper-free palladium-catalyzed Hiyama and Sonogashira cross-coupling reactions. The Sonogashira cross-coupling of estron-3-yl imidazylate afforded the corresponding phenylacetylene derivative in excellent yield. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Microwave-Promoted Suzuki-Miyaura Cross-Coupling of Aryl Imidazolylsulfonates in Water
  作者：José F. Cívicos、Diego A. Alonso、Carmen Nájera

  DOI：10.1002/adsc.201200364

  日期：2012.10.8

  Aryl imidazol-1-ylsulfonates are efficiently cross-coupled with potassium aryl- and alkenyltrifluoroborates in neat water under microwave heating (40 W, 110 °C) using 0.5 mol% of oxime palladacycle 1a, hexadecyltrimethyl ammonium bromide (CTAB) as additive, and triethylamine as base. Under these simple phosphane-free reaction conditions a wide array of biaryl, stilbene and styrene derivatives has been

  使用0.5 mol％的肟基丙二环1a，十六烷基三甲基溴化铵（CTAB）作为添加剂，在微波加热（40 W，110°C）下，于纯净水中将芳基咪唑-1-基磺酸盐与芳基钾和烯基三氟硼酸钾有效地交叉偶联。三乙胺为碱。在这些简单的无膦反应条件下，仅需30分钟即可制备出多种多样的联芳基，二苯乙烯和苯乙烯衍生物，并具有良好的高收率，并且具有较高的区域选择性和非对映选择性。