N-(4-methoxybenzyl)-4-nitrobenzenesulfonamide | 171414-17-8

• 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: N-(4-methoxybenzyl)-4-nitrobenzenesulfonamide
• 英文别名: N-[(4-methoxyphenyl)methyl]-4-nitrobenzenesulfonamide
• CAS: 171414-17-8
• 化学式: C₁₄H₁₄N₂O₅S
• mdl: MFCD01212709
• 分子量: 322.342
• InChiKey: RVRDNSLFNJNMLR-UHFFFAOYSA-N

物化性质

• 沸点：
  518.5±60.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-4-nitrobenzenesulfonamide 在 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 以66%的产率得到4-amino-N-(4-methoxybenzyl)benzenesulfonamide
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050
• 作为产物：
  描述：

  在 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以0.2 mg的产率得到N-(4-methoxybenzyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  通过电化学生成的苄基氨基ulf离子进行的无金属苯甲胺CH胺化反应

  摘要：

  在N-甲苯磺酰基二苯硫亚胺的存在下对甲苯衍生物进行电化学氧化，得到相应的苄基氨基离子，将其在非电解条件下用碘化四丁基铵处理，得到N-甲苯磺酰基苄基胺。该转变可作为无金属和化学氧化剂的苄基CH氨基化方法。由于N-甲苯磺酰基二苯硫亚胺具有很高的氧化潜能，因此本方法可用于从功能化的甲苯衍生物合成各种苄胺。

  DOI：

  10.1002/chem.201604484

文献信息

• Copper-Catalyzed One-Pot Approach to α-Aryl Amidines via Truce-Smiles Rearrangement
  作者：Ying Huang、Weiyin Yi、Qihui Sun、Fengping Yi

  DOI：10.1002/adsc.201800490

  日期：2018.8.17

  A copper‐catalyzed one‐pot approach to α‐aryl amidines from terminal alkynes, sulfonyl azides, and aryl sulfonamides via a Truce‐Smiles rearrangement under mild condition in good to excellent yields was reported for the first time. The formation of such aryl‐sp3 C−C bond previously could not be directly achieved by the common method. The stoichiometry of substrates played an important role in improving

  首次报道了在温和条件下通过Truce-Smiles重排以良好或优异的收率通过末端催化的炔烃，磺酰叠氮化物和芳基磺酰胺的铜催化单锅法。这种芳基-sp 3 C-C键的形成以前无法通过常规方法直接实现。底物的化学计量在提高所需产物的产率中起重要作用。此外，在α-芳基am的1 H NMR光谱中观察到两组信号，并且还通过对照实验研究了它们的可能原因。
• Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents
  作者：Megan Hopkins、Zachary Brandeburg、Andrew Hanson、Angus Lamar

  DOI：10.3390/molecules23081838

  日期：——

  Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes, sulfonamides, and PhI(OAc)2 under practical and mild reaction conditions has been developed. According to mechanistic studies described within, the reaction

  用于直接安装磺酰胺功能的替代合成方法是药物发现和开发领域内的一个非常理想的目标。已经开发出在实用和温和的反应条件下从一系列醛、磺酰胺和 PhI(OAc)2 形成具有合成价值的 N-磺酰基亚胺。根据其中描述的机理研究，反应通过初始步骤进行，该步骤涉及自由基引发剂（由可见光或热产生）以激活反应底物。该反应提供了一种合成有用且操作简单、相对温和的替代方法，可替代使用稳定、广泛可用的试剂的 N-磺酰基亚胺的传统形成。
• 2- and 4-Nitrobenzenesulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of amines
  作者：Tohru Fukuyama、Chung-Kuang Jow、Mui Cheung

  DOI：10.1016/0040-4039(95)01316-a

  日期：1995.9

  4-Nitrobenzenesulfonamides, readily prepared from primary amines, undergo smooth alkylation by Mitsunobu reaction or by conventional methods to give N-alkylated sulfonamides in near quantitative yields. These sulfonamides could be deprotected readily via Meisenheimer complexes upon treatment with thiolates in DMF at room temperature, giving secondary amines in high yields.

  由伯胺容易制备的2-和4-硝基苯磺酰胺通过Mitsunobu反应或通过常规方法进行平滑烷基化，以接近定量的产率得到N-烷基化磺酰胺。这些磺酰胺在室温下在DMF中用硫醇盐处理后，可以很容易地通过Meisenheimer配合物脱保护，从而以高收率得到仲胺。
• Catalyst-Free Alkylation of Sulfinic Acids with Sulfonamides via sp³ C−N Bond Cleavage at Room Temperature
  作者：Cong-Rong Liu、Man-Bo Li、Dao-Juan Cheng、Cui-Feng Yang、Shi-Kai Tian

  DOI：10.1021/ol900788r

  日期：2009.6.18

  alkylation of sulfinic acids with sulfonamides has been developed via sp3 C−N bond cleavage at room temperature. In the absence of external catalysts and additives, a wide variety of N-benzylic and N-allylic sulfonamides couple with sulfinic acids to give structurally diversified sulfones in moderate to excellent yields. Furthermore, the reaction of N-(2-acyl)allylic sulfonamides with sulfinic acids provides

  通过在室温下通过sp 3 C-N键裂解，开发了一种前所未有的亚磺酸与磺酰胺的无催化剂烷基化反应。在没有外部催化剂和添加剂的情况下，各种各样的N-苄基和N-烯丙基磺酰胺与亚磺酸偶联，以中等至极好的收率得到结构多样化的砜。此外，N-（2-酰基）烯丙基磺酰胺与亚磺酸的反应提供了具有独有的Z选择性的三取代烯丙基砜的便利途径。
• Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile
  作者：Jin Heui Choi、Byung Choon Lee、Hai Whang Lee、Ikchoon Lee

  DOI：10.1021/jo0161835

  日期：2002.2.1

  The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 degrees C have been studied. The reactions proceed competitively by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analyses of the Hammett and Brönsted coefficients together with the cross-interaction constants rho(XY), rho(YZ)

  研究了芳基苯磺酸盐（YC6H4SO2OC6H4Z）与苄胺（XC6H4CH2NH2）在乙腈中于65.0摄氏度下的反应。反应通过SO（kS-O）和CO（kC-O）键分裂而竞争地进行，但前者提供了主要的反应途径。在分析Hammett和Brönsted系数以及交叉相互作用常数rho（XY），rho（YZ）和rho（XZ）的基础上，提出了通过限速形成SO键裂解的逐步机理三角-双锥体五元（TBP-5C）中间体，而CO键断裂则是通过限速从Meisenheimer型络合物中排出磺酸根阴离子（YC6H4SO3-）来进行的。