N-methyl-4-nitro-N-(phenylthio)benzenamine | 110228-59-6

• 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-methyl-4-nitro-N-(phenylthio)benzenamine
• 英文别名: N-methyl-4'-nitrobenzenesulphenanilide；N-methyl-4'-nitrobenzenesulfenanilide；N-methyl-4-nitro-N-phenylsulfanylaniline
• CAS: 110228-59-6
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: PIBOUFJUYKYWTR-UHFFFAOYSA-N

物化性质

• 熔点：
  46-48 °C(Solv: pentane (109-66-0))
• 沸点：
  420.4±47.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-4-nitro-N-(phenylthio)benzenamine 以14%的产率得到
  参考文献：
  名称：

  BENATI L.; MONTEVECCHI P. C.; SPAGNOLO P., J. CHEM. SOC. PERKIN TRANS,(1987) N 1, 99-103

  摘要：

  DOI：
• 作为产物：
  描述：

  苯硫酚 在 磺酰氯 、 三乙胺 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 2.08h， 生成 N-methyl-4-nitro-N-(phenylthio)benzenamine
  参考文献：
  名称：

  Catalytic Thia-Sommelet−Hauser Rearrangement: Application to the Synthesis of Oxindoles

  摘要：

  A series of 3-arylthio-1,3-disubstituted-oxindoles were prepared in good yields by the reaction of alpha-diazocarbonyl compounds and sulfenamides. The reaction involves a Rh-catalyzed thia-Sommelet-Hauser-type rearrangement.

  DOI：

  10.1021/ol200091k

文献信息

• The reaction of benzenesulfenanilides with lewis acids: involvement of radical cation intermediates.
  作者：Loris Grossi、Pier Carlo Montevecchi

  DOI：10.1016/s0040-4020(01)91226-8

  日期：1993.1

  afford the radical cation intermediates 9a–c, some of which could be detected by e.p.r. spectroscopy. Thus, the 4′-methoxy substituted compound 1a gave the fairly persistent radical cation 9a. In contrast, the radical cation 9b, derived from the 4′-nitro substituted compound 4b, was not detected apparently because it decayed too rapidly forming the very stable radical cation 11b, intermediate in the formation

  4'-取代的N-甲基苯硫基苯胺1a-c与路易斯酸（包括BF 3，AlCl 3和GaCl 3）反应，得到自由基阳离子中间体9a-c，其中一些可以通过电子光谱法检测。因此，4'-甲氧基取代的化合物1a给出了相当持久的自由基阳离子9a。相反，显然没有检测到衍生自4'-硝基取代的化合物4b的自由基阳离子9b，因为它分解得太快而形成非常稳定的自由基阳离子11b，这是重排硫化物10b形成的中间过程。。自由基中间体9a-c与环己烯反应，生成1,2-加合物4a-c，5和6，据信它们是由th离子7b或硫烷8a，c形成的。
• Boron trifluoride-promoted reaction of 4′-nitrobenzenesulphenanilide and its N-methyl derivative with alkynes
  作者：Luisa Benati、P. Carlo Montevecchi、Piero Spagnolo

  DOI：10.1039/c39870001050

  日期：——

  4′-Nitrobenzenesulphenanilide and its N-methyl derivative react with alkynes in the presence of boron trifluoride–diethyl ether presumably affording thiirenium ion intermediates, which are trapped by acetonitrile to give eventually β-acetamidinovinyl sulphides.

  在三氟化硼-乙醚的存在下，4'-硝基苯磺酰苯胺及其N-甲基衍生物与炔烃反应，可能提供th离子中间体，这些中间体被乙腈捕获，最终生成β-乙酰胺基乙烯基硫化物。
• Benati, Luisa; Montevecchi, Pier Carlo; Spagnolo, Piero, Journal of the Chemical Society. Perkin transactions I, 1987, p. 99 - 104
  作者：Benati, Luisa、Montevecchi, Pier Carlo、Spagnolo, Piero

  DOI：——

  日期：——
• Benati, Luisa; Montevecchi, P. Carlo; Spagnolo, Piero, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1105 - 1111
  作者：Benati, Luisa、Montevecchi, P. Carlo、Spagnolo, Piero

  DOI：——

  日期：——
• Reactions of tosyl azide with 2-phenoxy- and 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione. Unexpected reactivity of intermediate 4-acyl-5-hydroxy-1-tosyltriazolines
  作者：Luisa Benati、Gianluca Calestani、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1039/p19950001381

  日期：——

  The reaction of tosyl azide 1 with 2-phenoxy-2;3-dihydro-1H-indane-1,3-dione 2c, carried out in hexamethylphosphoramide (HMPA) or in diethyl ether in the presence of triethylamine, fails to afford the expected diazo transfer product, i. e. the diazoacetophenone 3c (3c'), but instead leads to the dimeric indanedione 7 the formation of which is primarily ascribable to preferential fragmentation of the transient hydroxytriazoline 4c to give zwitterion 9c and dinitrogen. Under comparable conditions, tosyl azide 1 and 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione 2d in HMPA gives the ring-expanded hydroxybenzopyran 15, the formation of which is similarly ascribed to preferential fragmentation of the corresponding 4,5-dihydro-1H-triazole 4d to give zwitterion 9d. However, analogous reaction of the dione 2d in THF, in the presence of triethylamine, affords 2-diazo-2,3-dihydro-1H-indane-1,3-dione along with diphenyl disulfide, toluene-p-sulfonamide and phenyl toluene-4-thiosulfonate. These latter-products are believed to arise from ready decomposition of the 4,5-dihydro-1 H-triazole 4d precursor, i.e the triazenyl anion 13. X-Ray crystal structure analyses of compound 7 and the acetoxybenzopyran 17 are also reported.