4-methylphenyl 2-nitrophenyl disulfide | 54848-83-8

• 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: 4-methylphenyl 2-nitrophenyl disulfide
• 英文别名: 2-nitro-4'-methyldiphenyl disulfide；(2-nitro-phenyl)-p-tolyl disulfide；(2-Nitro-phenyl)-p-tolyl-disulfid；(2-Nitro-phenyl)-(4-methyl-phenyl)-disulfid；4-Methyl-2'-nitro-diphenyldisulfid；2-Nitro-4'-methyldiphenyldisulfid；1-[(4-Methylphenyl)disulfanyl]-2-nitrobenzene
• CAS: 54848-83-8
• 化学式: C₁₃H₁₁NO₂S₂
• 分子量: 277.368
• InChiKey: FOJKQGZIUZLHTL-UHFFFAOYSA-N

物化性质

• 熔点：
  73-73.8 °C
• 沸点：
  394.5±35.0 °C(Predicted)
• 密度：
  1.34±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：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-nitrophenyl disulfide 、 双苯磺酸甲烷 在 sodium methylate 作用下， 生成 bis-benzenesulfonyl-p-tolylsulfanyl-methane
  参考文献：
  名称：

  Leandri; Tundo, Annali di Chimica, 1954, vol. 44, p. 518,520, 521

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[(O-硝基苯基)硫代]-L-苏氨酸 在 对甲苯磺酸 、 4-甲苯硫酚 、 4-溴苯磺酰氯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 4-methylphenyl 2-nitrophenyl disulfide
  参考文献：
  名称：

  Synthesis and acylation of salts of L-threonine .beta.-lactone: a route to .beta.-lactone antibiotics

  摘要：

  The synthesis and N-acylation of beta-lactones derived from L-threonine and L-allo-threonine were investigated. Treatment of N-[(o-nitrophenyl)sulfenyl]-L-threonine (7a) and N-[(o-nitrophenyl)sulfenyl]-L-allo-threonine (7b) with 4-bromobenzenesulfonyl chloride in pyridine at -43 to -0-degrees-C gives the corresponding-beta-lactones 8a and 8b, respectively, in 45-56% yields. These can be deprotected with thiophenol or p-thiocresol in the presence of p-toluenesulfonic acid to produce optically pure salts of L-threonine-beta-lactone (9a) and its allo isomer 9b (65-92%). Compound 9a is readily acylated by reagents such as acid chlorides (e.g., acetyl, benzoyl) and mixed anhydrides to afford N-acyl-beta-substituted-beta-lactones such as 10 (antibiotic SQ 26,517), 14, 15, and 16 in good yield (84-92%). Reaction of beta-lactones 8a, 8b, and 9a with HBr in acetic acid results in nucleophilic ring opening by bromide at the beta-position to give pure isomers of 2-amino-3-bromobutanoic acid.

  DOI：

  10.1021/jo00003a062

文献信息

• Reactions of aromatic sulphenyl compounds with organotin compounds
  作者：James L. Wardell、Siddique Ahmed

  DOI：10.1016/s0022-328x(00)80488-x

  日期：1974.10

  aryltin bonds, ArSn, when the aryl groups contain strongly electron releasing substituents, to give monosulphides, RSAr. The reaction of o-NO2C6H4SCl and Ph3SnCHCH2 gave both the cleavage product, CH2CHSC6H4NO2-o, and the addition product, Ph3SnCHClCH2SC6H4NO2-o. Other organotin bonds cleaved by o-NO2C6H4SCl are p-MeC6H4SCH2CH2Sn (to give p-MeC6H4SSC6H4NO2-o) and allyltin bonds, which yield both rearranged

  当芳基含有强电子释放取代基时，芳族亚硫酰卤和硫氰酸盐RSX会裂解芳基键ArSn，从而生成单硫化物RSAr。的反应Ô -NO 2 ç 6 ħ 4 SCL和博士3 SnCHCH 2给了两个裂解产物，CH 2 CHSC 6 ħ 4 NO 2 - Ó，和加成产物中，Ph 3 SnCHClCH 2 SC 6 H ^ 4 NO 2 - o。其他有机锡键被o -NO 2裂解Ç 6 ħ 4 SCL均为p -MeC 6 ħ 4 SCH 2 CH 2 Sn（以得到p -MeC 6 ħ 4 SSC 6 ħ 4 NO 2 - ö）和allyltin债券，其产生两个重排和未重排的烯丙基硫化物。
• Reactions of organotin sulphides II. Cleavage of organotin sulphides by aromatic sulphenyl compounds and divalent sulphur chlorides
  作者：J.L. Wardell、P.L. Clarke

  DOI：10.1016/s0022-328x(00)82615-7

  日期：1971.2

  with organotin alkyl and aryl sulphides, R3SnSR and R2Sn(SR)2; trisulphides were produced from bis(trialkyltin) sulphides, (R3Sn)2S, or dialkyltin sulphides, R2SnS, and sulphenyl halides and thiocyanates, as well as from sulphur dichloride and organotin aryl sulphides; tetrasulphides were formed from disulphur dichloride and organotin aryl sulphides.

  已经研究了亚硫基化合物和氯化硫与有机锡硫化物的反应。二氯化硫和二氯化二硫都与有机锡硫化物反应，亚硫基溴化物ArSBr，氯化物ArSCl和硫氰酸盐ArSSCN一样，但亚硫基氰化物ArSCN，亚磺酰胺ArSNR 2，亚硫基酯ArSOR和二硫化物ArSSAr没有反应。从亚硫酰卤和硫氰酸酯与有机锡烷基和芳基硫醚，R 3 SnSR和R 2 Sn（SR）2一起获得二硫化物产物；三硫化物由双（三烷基锡）硫化物（R 3 Sn）2 S或二烷基锡硫化物R 2产生SnS，亚磺酰卤和硫氰酸盐，以及二氯化硫和有机锡芳基硫化物；由二氯化二硫和有机锡芳基硫化物形成四硫化物。
• Nakazaki, Journal of the Institute of Polytechnics, Osaka City University, Series C: Chemistry, 1953, vol. <C> 4, p. 100
  作者：Nakazaki

  DOI：——

  日期：——
• Stepanov,B.I. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 334 - 338
  作者：Stepanov,B.I. et al.

  DOI：——

  日期：——
• Rheinboldt; Giesbrecht, Justus Liebigs Annalen der Chemie, 1950, vol. 568, p. 198,212
  作者：Rheinboldt、Giesbrecht

  DOI：——

  日期：——