1-propylthio-4-nitrobenzene | 27826-42-2

• 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: 1-propylthio-4-nitrobenzene
• 英文别名: Benzene, 1-nitro-4-(propylthio)-；1-nitro-4-propylsulfanylbenzene
• CAS: 27826-42-2
• 化学式: C₉H₁₁NO₂S
• 分子量: 197.258
• InChiKey: ZKRRTBXZRJXUJO-UHFFFAOYSA-N

物化性质

• 沸点：
  315.8±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-propylthio-4-nitrobenzene 在 盐酸 、 tin 作用下， 反应 0.25h， 以85.6%的产率得到4-(硫代丙基)苯胺 1盐酸盐
  参考文献：
  名称：

  Sulfoxide-Containing Aromatic Nitrogen Mustards as Hypoxia-Directed Bioreductive Cytotoxins

  摘要：

  A series of diaryl and alkylaryl sulfoxide-containing nitrogen mustards were synthesized and evaluated for their hypoxia-selective cytotoxicity against V-79 cells in vitro as well as for their metabolism profiles with the rat S-9 fractions. In general, the diaryl sulfoxides (4, 5, and 7-9) showed much greater hypoxia selectivity (11-27-fold) than the alkylaryl sulfoxides (similar to3-fold) (1 and 3). The fused diphenyl sulfoxides (10 and 11), on the other hand, showed very low hypoxia selectivity (1.3-3-fold). Compound 10 was highly cytotoxic under both aerobic and anaerobic conditions, while 11 showed low cytotoxicity under both conditions. The bioreduction of 8 by the rat S-9 fraction under anaerobic conditions was inhibited by menadione and enhanced by benzaldehyde, acetaldehyde, or 2-hydroxypyrimidine suggesting the involvement of aldehyde oxidase in the reduction of the sulfoxides. Bioreductive metabolism studies of selected model sulfoxides suggested that diaryl sulfoxides are better substrates for aldehyde oxidase than alkylaryl sulfoxides.

  DOI：

  10.1021/jm9904957
• 作为产物：
  描述：

  1-Nitro-4-(propane-1-sulfinyl)-benzene 在 1,3,5-三甲氧基苯 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到1-propylthio-4-nitrobenzene
  参考文献：
  名称：

  来自氯ulf盐的亲电子氯：亚砜的高度化学选择性还原。

  摘要：

  本文中，我们基于氯ulf盐的新应用描述了亚砜的选择性后期脱氧，并展示了使用这些亚砜原位生成的物种作为亲电氯源的新工艺。首次描述了使用高度亲核的1,3,5-三甲氧基苯（TMB）作为还原剂，并将其用于简单和功能化亚砜的脱氧。该方法易于操作，经济，适用于克级操作，并且易于应用于多官能分子，如超过45个实例（包括商业药物和类似物）所示。我们还报告了定义更具反应性的亚砜的竞争实验的结果，并且我们根据底物和产品的观察结果提出了一种机械的方案。

  DOI：

  10.1002/chem.202001815

文献信息

• Sulfite-Promoted One-Pot Synthesis of Sulfides by Reaction of Aryl Disulfides with Alkyl Halides
  作者：Ping Zhong、Ri-yuan Tang、Qiu-lian Lin

  DOI：10.1055/s-2006-950363

  日期：2007.1

  dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free

  开发了一种连二亚硫酸钠、硫代硫酸钠和雕白粉在室温下促进芳基烷基硫醚的一锅法合成。一系列二硫化物与卤代烷的反应在雕白粉的存在下顺利进行。讨论了可能的反应途径，并研究了这些亚硫酸盐对二硫化物的影响。该协议的重要特点是无金属、无强碱、反应条件温和、操作简单、反应时间短、产品收率高。
• Enantioselective Nitrene Transfer to Sulfides Catalyzed by a Chiral Iron Complex
  作者：Jun Wang、Marcus Frings、Carsten Bolm

  DOI：10.1002/anie.201304451

  日期：2013.8.12

  Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated.

  铁厂：通过手性铁（III）/ PyBOX催化剂（参见方案）可实现对映选择性的腈转化为硫化物。因此以高对映选择性和产率获得了各种磺酰亚胺。还证明了该方案在对映体富集的亚砜亚胺和环氧化物的合成中的应用。
• Microwave efficient S-arylation of thiols with aryl iodides using supported metal nanoparticles
  作者：Camino Gonzalez-Arellano、Rafael Luque、Duncan J. Macquarrie

  DOI：10.1039/b818767c

  日期：——

  An efficient and green microwave-assisted heterogeneous S-arylation protocol, reported for the first time, provided excellent coupling conversions and selectivities in minutes of reaction using Fe (homocoupling) and Cu (cross-coupling) supported metal nanoparticles.

  首次报道的一种高效且绿色的微波辅助异质S-芳构化方案在使用Fe（均偶联）和Cu（交叉偶联）负载的金属纳米颗粒的反应分钟内提供了出色的偶联转化率和选择性。
• One-Pot Synthesis of Sulfides by Reaction of Disulfides with Alkyl Halides in the Presence of Sodium Dithionite
  作者：Ri-Yuan Tang、Ping Zhong、Qiu-lian Lin

  DOI：10.1080/10426500600892479

  日期：2007.1.1

  Sodium dithionite-promoted synthesis of unsymmetrical diorganyl sulfides by a reaction of diaryl disulfides with alkyl halides at r.t. has been developed. The advantages offered by this method are operational simplicity, a faster reaction, neutral and mild reaction conditions, and moderate to good yields of products.

  已经开发了通过二芳基二硫化物与烷基卤在室温下反应合成不对称二有机基硫化物的连二亚硫酸钠促进的合成。该方法的优点是操作简单，反应速度快，反应条件中性温和，产品收率中等至良好。
• The Dependence of Ionic Liquid Solvent Effects on the Nucleophilic Heteroatom in S _N Ar Reactions. Highlighting the Potential for Control of Selectivity
  作者：Karin S. Schaffarczyk McHale、Ronald S. Haines、Jason B. Harper

  DOI：10.1002/cplu.201900173

  日期：2019.5

  Nucleophilic aromatic substitution (SN Ar) reactions of 1-fluoro-4-nitrobenzene using similar nitrogen and sulfur nucleophiles were studied through extensive kinetic analysis in mixtures containing ionic liquids. The interactions of the ionic liquid components with the starting materials and transition state for each process were investigated in an attempt to construct a broad predictive framework

  通过对含离子液体的混合物进行广泛的动力学分析，研究了使用类似的氮和硫亲核试剂的1-氟-4-硝基苯的亲核芳香取代（SN Ar）反应。研究了离子液体组分与每种方法的起始原料和过渡态之间的相互作用，以试图为离子液体如何影响反应结果建立一个广泛的预测框架。已经发现，基于活化参数，对于所考虑的每个亲核试剂，微观相互作用以及因此离子液体溶剂的作用是不同的。这项研究的结果表明，可能有可能合理地选择给定的离子液体混合物来选择性地控制存在多个亲核试剂的SN Ar反应的反应结果。