1-((ethylsulfonyl)methyl)-4-nitrobenzene | 1612-41-5

• 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-((ethylsulfonyl)methyl)-4-nitrobenzene
• 英文别名: Ethyl-(p-nitro-benzyl)-sulfon；Ethyl-(4-nitro-benzyl)-sulfon；ethyl-(4-nitro-benzyl)-sulfone；4-Nitro-α-aethylsulfon-toluol；Aethyl-(4-nitro-benzyl)-sulfon；1-[(Ethanesulfonyl)methyl]-4-nitrobenzene；1-(ethylsulfonylmethyl)-4-nitrobenzene
• CAS: 1612-41-5
• 化学式: C₉H₁₁NO₄S
• mdl: MFCD22054831
• 分子量: 229.257
• InChiKey: QRLVYWVPKPUBJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143.5 °C
• 沸点：
  461.3±28.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  1-((ethylsulfonyl)methyl)-4-nitrobenzene 生成 4-ethanesulfonylmethyl-aniline
  参考文献：
  名称：

  DE623883

  摘要：

  公开号：
• 作为产物：
  描述：

  乙烷亚磺酸钠 、 对硝基溴化苄 在 乙醇 作用下， 生成 1-((ethylsulfonyl)methyl)-4-nitrobenzene
  参考文献：
  名称：

  Blackburn; Challenger, Journal of the Chemical Society, 1938, p. 1875

  摘要：

  DOI：

文献信息

• Copper-Mediated Decarboxylative Sulfonylation of Arylacetic Acids with Sodium Sulfinates
  作者：Yinrong Wu、Jiewen Chen、Lu Li、Kangmei Wen、Xingang Yao、Jianxin Pang、Ting Wu、Xiaodong Tang

  DOI：10.1021/acs.orglett.0c02516

  日期：2020.9.18

  Herein, we present a copper-mediated decarboxylative sulfonylation of arylacetic acids with sodium sulfinates that provides viable access to sulfone compounds. This protocol features readily available feedstocks, simple operations, high regioselectivities, and moderate to good yields. The newly obtained products could be converted to other useful compounds. Importantly, the products and their derivatives

  在这里，我们介绍了铜磺酸与亚磺酸钠介导的芳基丙烯酸的脱羧磺酰化，提供了通向砜类化合物的可行途径。该方案的特点是易于获得的原料，操作简单，区域选择性高以及中等至良好的收率。新获得的产物可以转化为其他有用的化合物。重要的是，产物和它们的衍生物在体外表现出有效的抗肿瘤活性，这通过MTT测定法进行了测试。
• Photosensitized Oxygenation of Benzyl Ethyl Sulfide
  作者：S. M. Bonesi、M. Mella、N. d'Alessandro、G. G. Aloisi、M. Vanossi、A. Albini

  DOI：10.1021/jo9817927

  日期：1998.12.1

  Singlet oxygen adds to benzyl ethyl sulfide (5, total quenching rate ca. 1 x 10(7) M-1 s(-1), little dependent on the solvent) to ultimately give benzaldehyde (6) and a small amount of the sulfone (8) in aprotic media (rate of the chemical reaction in benzene 5.5 x 10(6) M-1 s(-1)) and mainly the sulfoxide (7) in protic media (1.1 x 10(7) M-1 s(-1) in methanol). In the presence of small amounts (0.002-0.3 M) of protic additives (alcohols, phenol, carboxylic acids), the sulfoxide becomes the main product in benzene also. Various evidence support the formation of two intermediates in aprotic solvents. The first one is an exciplex or a syn persulfoxide. It undergoes intramolecular hydrogen abstraction to give a ylide and finally benzaldehyde. Such rearrangement is either a concerted or a radicalic process and not a proton transfer (as indicated by the deuterium effect observed with the alpha-d benzyl sulfide and the occurrence of the process with the p-nitro and p-methoxy derivatives, 5' and 5 "). This intermediate is not quenched except under relatively strong acidic conditions. A second intermediate, arising either from the first one or through a parallel path, has the properties usually associated with the persulfoxide (possibly it is the anti rotamer). This species gives some sulfoxide but mainly decays to the unreacted sulfide; it can be trapped intermolecularly, however, both by acids and by diphenyl sulfoxide (in the latter case it gives more of sulfone 8 than of sulfoxide 7). The relative rates of protonation of both the first and the second intermediate (determined in benzene doped with protic additives) correlate with the gas-phase acidity of such additives. As for the reaction in neat alcohols and in benzene doped with acids, a single intermediate intervenes. This is better described as a S-hydroperoxy cation rather than a neutral hydroperoxysulfurane and is trapped by both diphenyl sulfoxide and sulfone at rates close to those measured for the photo-oxidation of diethyl sulfide.