1-(4-tert-butyl-phenylsulfanyl)-2-nitro-benzene | 3169-88-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(4-tert-butyl-phenylsulfanyl)-2-nitro-benzene
• 英文别名: 1-(4-Tert-butylphenyl)sulfanyl-2-nitrobenzene；1-(4-tert-butylphenyl)sulfanyl-2-nitrobenzene
• CAS: 3169-88-8
• 化学式: C₁₆H₁₇NO₂S
• 分子量: 287.382
• InChiKey: RHBNFNOWEREYOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-tert-butyl-phenylsulfanyl)-2-nitro-benzene 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 2-(4-tert-butylphenyl)sulfanylaniline
  参考文献：
  名称：

  dibenz [b，f] -1,4-thiazepine，-oxazep​​ine和dibenz [b，e] -azepine系列内酰胺的新合成。4.关于七元杂环的通信†

  摘要：

  通过在分子内应用异氰酸根合-二苯基硫化物，-二苯氧化物和-二苯基甲烷与AlCl 3在邻二氯苯中的LEUCKART酰胺合成方法，发现了一种能够以非常好的收率得到10,11-dihydro-11-oxo-dibenz [b，f分别为-1,4-噻氮平（VII），-氧杂氮平（VIII）和5,6-二氢-6-氧杂二苯并[b，e]-氮杂平（XI）。

  DOI：

  10.1002/hlca.19650480212
• 作为产物：
  描述：

  4-叔丁基苯硫酚 、 1-氟-2-硝基苯 在 potassium fluoride impregnated on clinoptilolite 、 air 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 以98%的产率得到1-(4-tert-butyl-phenylsulfanyl)-2-nitro-benzene
  参考文献：
  名称：

  KF/Clinoptilolite: An Efficient Promoter for the Synthesis of Thioethers

  摘要：

  负载氟化钾的天然沸石作为一种新型固体碱体系，能有效催化硫酚与缺电子氟代、氯代和溴代芳烃在二甲基亚砜中的偶联反应。这种多功能且高效的固体碱已被证明可使目标产物获得良好至优异的产率。该方法为二芳基硫醚的制备提供了一种便捷、高效且实用的途径。

  DOI：

  10.2174/1386207311316050002

文献信息

• Reduction of nitro- and nitroso-compounds by tervalent phosphorus reagents. Part VII. A new synthesis of phenothiazines involving a new molecular rearrangement
  作者：J. I. G. Cadogan、S. Kulik、C. Thomson、M. J. Todd

  DOI：10.1039/j39700002437

  日期：——

  Reductive cyclisation of aryl 2-nitroaryl sulphides by triethyl phosphite provides a new synthesis of phenothiazines (yields ca. 50–85%) which is superior to that involving the thermal decomposition of aryl 2-azidoaryl sulphides (yields ca. 30%). Both reactions proceed via a novel molecular rearrangement whereby, for example, 4-chlorophenyl 2-nitrophenyl sulphide gives 3-chlorophenothiazine, whereas 4

  亚磷酸三乙酯对芳基2-硝基芳基硫醚的还原环化提供了吩噻嗪的新合成方法（产率约50-85％），优于涉及芳基2-叠氮基芳基硫醚热分解的产率（约30％）。两个反应均通过新颖的分子重排进行，例如，4-氯苯基2-硝基苯基硫化物产生3-氯吩噻嗪，而4-氯-2-硝基苯基苯基硫化物产生2-氯吩噻嗪。[4- 2 H]苯基2-硝基苯基硫化物类似地得到[3- 2 H]吩噻嗪，如通过比较其阳离子自由基的esr光谱与计算机模拟的[2- 2 H]-和[3]比较- 2H]-吩噻嗪。还报道了吩噻嗪通过磷酸三乙酯的便利的N-乙基化。
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.
• Cadogan,J.I.G. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1749 - 1757
  作者：Cadogan,J.I.G. et al.

  DOI：——

  日期：——
• KF/Clinoptilolite: An Efficient Promoter for the Synthesis of Thioethers
  作者：Sadegh Salmanpour、Mohammad Khalilzadeh、Abolfazl Hosseini

  DOI：10.2174/1386207311316050002

  日期：2013.4.1

  Potassium fluoride impregnated on natural zeolite as a new solid base system effectively catalyzes the coupling of thiophenols with electron-deficient fluoro-, chloro- and bromo-arenes in DMSO. This versatile and efficient solid base has been demonstrated to afford the corresponding desired products in good to excellent yields. This procedure provides a convenient, efficient and practical method for the preparation of diaryl thioethers.

  负载氟化钾的天然沸石作为一种新型固体碱体系，能有效催化硫酚与缺电子氟代、氯代和溴代芳烃在二甲基亚砜中的偶联反应。这种多功能且高效的固体碱已被证明可使目标产物获得良好至优异的产率。该方法为二芳基硫醚的制备提供了一种便捷、高效且实用的途径。
• Neue Synthese von Lactamen der Dibenz[b,f]-1,4-thiazepin-, -oxazepin und Dibenz[b, e]-azepin-Reihe. 4. Mitteilung über siebengliedrige Heterocyclen
  作者：J. Schmutz、F. Künzle、F. Hunziker、A. Bürki

  DOI：10.1002/hlca.19650480212

  日期：——

  By intramolecular application of LEUCKART's amide synthesis using isocyanato-diphenylsulphides, -diphenyloxides and -diphenylmethanes with AlCl3 in o-dichlorobenzene a method has been found which gives in very good yields 10,11-dihydro-11-oxo-dibenz[b,f]-1,4-thiazepines (VII), -oxazepines (VIII), and 5,6-Dihydro-6-oxo-dibenz[b,e]-azepines (XI), respectively.

  通过在分子内应用异氰酸根合-二苯基硫化物，-二苯氧化物和-二苯基甲烷与AlCl 3在邻二氯苯中的LEUCKART酰胺合成方法，发现了一种能够以非常好的收率得到10,11-dihydro-11-oxo-dibenz [b，f分别为-1,4-噻氮平（VII），-氧杂氮平（VIII）和5,6-二氢-6-氧杂二苯并[b，e]-氮杂平（XI）。