4-nitro-N-(1-methyl-1-phenylethyl)benzenesulfonamide

• 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-nitro-N-(1-methyl-1-phenylethyl)benzenesulfonamide
• 英文别名: 4-nitro-N-(2-phenylpropan-2-yl)benzenesulfonamide
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: YCAAOQRBICMJGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 异丙苯 在 吡唑 作用下， 以 二氯甲烷 为溶剂， 生成 4-nitro-N-(1-methyl-1-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  从双（亚氨基）钌（VI）卟啉到碳氢化合物的亚氨基转移：亚氨基取代基、C-H键解离能和RuVI/V还原电位的影响

  摘要：

  [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

  DOI：

  10.1021/ja0542789

文献信息

• 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）。
• Rhodium(II)-catalyzed aziridinations and CH insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane
  作者：Paul M�ller、Corine Baud、Yvan Jacquier、Mary Moran、Ivo N�geli

  DOI：10.1002/(sici)1099-1395(199606)9:6<341::aid-poc791>3.0.co;2-5

  日期：1996.6

  The [Rh-2(OAc)(4)]-catalyzed decomposition of NsN=IPh [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane} in the presence of olefins affords aziridines in yields of up to 85%. The aziridination of cis-hex-2-ene and cis-beta- methylstyrene is stereospecific, but, cis-stilbene affords a 3:1 mixture of cis- and trans-aziridines in low yield. With chiral Rh(II) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN=IPh-[Rh-2(OAc)(4)] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.
• 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