n-butyl o-nitrophenyl disulfide | 63116-26-7

• 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-butyl o-nitrophenyl disulfide
• 英文别名: butyl o-nitrophenyl disulfide；2-Nitrophenylbutyldisulfid；1-(Butyldisulfanyl)-2-nitrobenzene
• CAS: 63116-26-7
• 化学式: C₁₀H₁₃NO₂S₂
• 分子量: 243.351
• InChiKey: UDEPRXITUZODII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁硫醇 、 N,N-dimethyl-o-nitrobenzenesulfenamide 在 三氟甲磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 n-butyl o-nitrophenyl disulfide
  参考文献：
  名称：

  Mechanism of nucleophilic substitution reactions of o-nitrobenzenesulfenamides: evidence for a substitution proceeding through a sulfuranide intermediate

  摘要：

  o-Nitrobenzenesulfenamides (1) undergo acid-catalyzed methanolysis (eq 2) in acetonitrile-methanol, affording methyl o-nitrobenzenesulfenate (2). They also undergo acid-catalyzed reaction with a thiol, giving an alkyl o-nitrophenyl disulfide (eq 3). In MeCN-8.2 M MeOH the thiolysis reaction exhibits a simple first-order dependence on both [R'SH] and [H+] for acid concentrations in the range 0.001-0.012 M. In marked contrast the rate of the methanolysis reaction is only slightly dependent on [H+] for the same range of acid concentrations. It is also markedly dependent on [MeOH], being seven times faster in MeCN-8.2 M MeOH than in MeCN-3.0 M MeOH. Measurement of the equilibrium constant for protonation of 1 to 1-H+ in MeCN-8.2 M MeOH shows that under the conditions used for the kinetic studies of eqs 2 and 3 the extent of protonation of 1 to 1-H+ is always small (<6%). Consideration of this fact, and the markedly different kinetic behavior of the two substitution reactions, leads to the following interpretation: (a) for the thiolysis the rate-determining step is the reaction of the thiol with 1-H+; (b) for the methanolysis, on the other hand, the mechanism is that shown in eq 9, where a sulfuranide species 4 is the key intermediate on the reaction coordinate. The lack of dependence of the rate on [H+] is because acid-catalyzed reversion of 4 to 1-H+ and methanol (Step k-6) is faster than the cleavage of 4 (step k7) to give 2 and R2NH. The methanolysis of 1 therefore represents another substitution at dicoordinate sulfur (similar to ref 10) where the kinetics require a mechanism with a hypervalent sulfur species as an intermediate on the reaction coordinate.

  DOI：

  10.1021/jo00038a013

文献信息

• Unsymmetric aryl–alkyl disulfide growth inhibitors of methicillin-resistant Staphylococcus aureus and Bacillus anthracis
  作者：Edward Turos、Kevin D. Revell、Praveen Ramaraju、Danielle A. Gergeres、Kerriann Greenhalgh、Ashley Young、Nalini Sathyanarayan、Sonja Dickey、Daniel Lim、Mamoun M. Alhamadsheh

  DOI：10.1016/j.bmc.2008.05.032

  日期：2008.7.1

  attack on the disulfide bond. Small alkyl residues on the other sulfur provide the best activity as well, which for different bacteria appears to be somewhat dependent on the nature of the alkyl moiety. The mechanism of action of these lipophilic disulfides is likely similar to that of previously reported N-thiolated beta-lactams, which have been shown to produce alkyl-CoA disulfides through a thiol-disulfide

  本研究描述了合成生产的混合芳烷基二硫化物化合物的抗菌特性，作为控制金黄色葡萄球菌和炭疽芽孢杆菌生长的一种手段。其中一些化合物具有很强的体外生物活性。我们的结果表明，在检查的 12 种不同的芳基取代基中，硝基苯基衍生物提供最强的抗生素活性。这可能是芳硫基部分作为离去基团对二硫键进行亲核攻击的电子活化的结果。其他硫上的小烷基残基也提供最佳活性，对于不同的细菌，这似乎在某种程度上取决于烷基部分的性质。这些亲脂性二硫化物的作用机制可能与之前报道的 N-硫醇化 β-内酰胺相似，已显示通过细胞质内的硫醇-二硫化物交换产生烷基-CoA 二硫化物，最终抑制 II 型脂肪酸合成。然而，混合的烷基辅酶 A 二硫化物本身没有抗菌活性，可能是由于高极性化合物不能穿过细菌细胞膜。已发现这些结构简单的二硫化物可抑制 β-酮酰基-酰基载体蛋白合酶 III 或 FabH（II 型脂肪酸生物合成中的关键酶），因此可作为开发针对
• 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：——
• STEPANOV B. I.; RODIONOV V. YA.; CHIBISOVA T. A.; YAGODINA L. A.; STANKEV+, ZH. ORGAN. XIMII, 1977, 13, HO 2, 370-374
  作者：STEPANOV B. I.、 RODIONOV V. YA.、 CHIBISOVA T. A.、 YAGODINA L. A.、 STANKEV+

  DOI：——

  日期：——