N-(1-(4-methoxyphenyl)ethyl)-4-nitrobenzenesulfonamide

• 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-(1-(4-methoxyphenyl)ethyl)-4-nitrobenzenesulfonamide
• 英文别名: N-[1-(4-methoxyphenyl)ethyl]-4-nitrobenzenesulfonamide
• 化学式: C₁₅H₁₆N₂O₅S
• 分子量: 336.368
• InChiKey: PHFDGICFWJWRQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基苯磺酰胺 、 4-乙基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 dichloro(2,2′-bipyridine)gold(III) chloride 作用下， 以 乙腈 为溶剂， 以71%的产率得到N-(1-(4-methoxyphenyl)ethyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  金（III）催化的苄基的C-H键的分子间的酰胺化†

  摘要：

  描述了金（III）催化的苄基CH键与磺酰胺和羧酰胺的分子间酰胺化反应。Au-bipy配合物/ N-溴代琥珀酰亚胺系统的协议为通过CH活化合成各种酰胺提供了实际应用。反应以高效率进行，得到相应的胺，它们是非常有用的合成中间体。

  DOI：

  10.1039/c2ob26857d

文献信息

• Imido Transfer from Bis(imido)ruthenium(VI) Porphyrins to Hydrocarbons:  Effect of Imido Substituents, C−H Bond Dissociation Energies, and Ru^VI/V Reduction Potentials
  作者：Sarana Ka-Yan Leung、Wai-Man Tsui、Jie-Sheng Huang、Chi-Ming Che、Jiang-Lin Liang、Nianyong Zhu

  DOI：10.1021/ja0542789

  日期：2005.11.30

  (BDE) of the hydrocarbons. A linear correlation was observed between log k' (k' is the k2 value divided by the number of reactive hydrogens) and BDE and between log k2 and E(1/2)(Ru(VI/V)); the linearity in the former case supports a H-atom abstraction mechanism. The amidation by [Ru(VI)(TMP)(NNs)2] reverses the thermodynamic reactivity order cumene > ethylbenzene/toluene, with k'(tertiary C-H)/k'(secondary

  [Ru(VI)(TMP)(NSO2R)2]（SO2R = Ms、Ts、Bs、Cs、Ns；R = p-C6H4OMe、p-C6H4Me、C6H5、p-C6H4Cl、p-C6H4NO2）和[ Ru(VI)(Por)(NTs)2] (Por = 2,6-Cl2TPP, F20-TPP) 是通过 [Ru(II)(Por)(CO)] 与 PhI=NSO2R 在 CH2Cl2 中的反应制备的。这些配合物表现出可逆的 Ru(VI/V) 对，E(1/2) = -0.41 到 -0.12 V vs Cp2Fe(+/0)，并与苯乙烯、降冰片烯、顺式环辛烯、茚、乙苯进行酰亚胺转移反应，枯烯、9,10-二氢蒽、呫吨、环己烯、甲苯和四氢呋喃以高达 85% 的产率提供氮丙啶或酰胺。298 K 氮丙啶化/酰胺化反应的二级速率常数 (k2) 确定为 (2.6 +/- 0.1) x 10(-5) 至 14.4 +/- 0.6
• Rhodium(II)-Catalyzed CH Insertions with {[(4-Nitrophenyl)sulfonyl]imino}phenyl-λ³-iodane
  作者：Ivo Nägeli、Corine Baud、GéErald Bernardinelli、Yvan Jacquier、Mary Moraon、Paul Müllet

  DOI：10.1002/hlca.19970800407

  日期：1997.6.30

  in formal insertions into CH bonds, activated by phenyl or vinyl groups, or by O-substituents. Scope and limitations of the reaction were investigated. Yields of up to 84% were achieved in the most favorable cases. Yields were enhanced by electron-releasing substituents and decreased by steric hindrance. Aziridination competed with allylic insertion with olefinic substrates. The insertion reaction proceeded

  所述的[Rh 2（OAc）4 ]的催化的分解[（4-硝基苯基）磺酰基]亚氨基}苯基-λ 3 -iodane（NsNIPh）导致正式插入到CH键，被苯基或乙烯基活化，或通过O-取代基。研究了反应的范围和局限性。在最有利的情况下，产率高达84％。释放电子的取代基提高了产率，而空间位阻降低了产率。叠氮化与烯烃底物的烯丙基插入竞争。插入反应在保持构型的情况下进行。使用手性Rh II催化剂，观察到适度的不对称诱导。提出了一种机制，涉及通过Rh络合的腈直接插入CH键。
• Iodine-Catalyzed Aminosulfonation of Hydrocarbons by Imidoiodinanes. a Synthetic and Mechanistic Investigation
  作者：Angus A. Lamar、Kenneth M. Nicholas

  DOI：10.1021/jo1015213

  日期：2010.11.19

  benzylic and some aliphatic saturated and unsaturated hydrocarbons by reaction with imido-iodinanes (PhI═NSO2Ar) is catalyzed by I2 under operationally simple and mild conditions. The first examples of 1,2-functionalization of unactivated C−H bonds using imido-iodinanes as aminating agents are reported. Mechanistic investigations, including Hammett analysis, kinetic isotope effects, a cyclopropane clock experiment

  的范围和苄一些脂肪族饱和及不饱和烃通过与亚氨基- iodinanes（PhI═NSO反应的氨基官能化2 Ar）之由I催化2操作简单和温和的条件下。报道了使用亚氨基碘烷作为胺化剂的未活化CH键的1，2-官能化的第一个例子。包括哈米特分析，动力学同位素效应，环丙烷钟实验和立体选择性试验在内的机理研究表明，CN键形成过程中存在逐步的途径。对活性胺化物种的性质的研究已导致分离出一种新的胺化剂，其配方为（ArSO 2 N）x I y（x= 1，y = 2；或x = 3，y = 4）。
• Copper-Catalyzed Intermolecular Hydroamination of Alkenes
  作者：Jason G. Taylor、Neil Whittall、King Kuok (Mimi) Hii

  DOI：10.1021/ol061355b

  日期：2006.8.1

  Regioselective additions of arylsulfonamides to vinylarenes, norbornene, and cyclohexadiene were achieved using a copper-diphosphine catayst under mild reaction conditions. These processes appear to be ligand-accelerated.
• Au(iii)-catalyzed intermolecular amidation of benzylic C–H bonds
  作者：Yan Zhang、Bainian Feng、Chengjian Zhu

  DOI：10.1039/c2ob26857d

  日期：——

  Au(III)-catalyzed intermolecular amidations of benzylic C–H bonds with sulfonamides and carboxamides are described. The protocol with the Au–bipy complex/N-bromosuccinimide system provides practical applications for synthesis of various amides via C–H activations. The reaction proceeds with high efficiency to give the corresponding amines, which are extremely useful synthetic intermediates.

  描述了金（III）催化的苄基CH键与磺酰胺和羧酰胺的分子间酰胺化反应。Au-bipy配合物/ N-溴代琥珀酰亚胺系统的协议为通过CH活化合成各种酰胺提供了实际应用。反应以高效率进行，得到相应的胺，它们是非常有用的合成中间体。