4-硝基苯磺酸正丁酯 | 4028-52-8

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸盐/亚磺酸盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-硝基苯磺酸正丁酯
• 英文名称: n-butyl-4-nitrobenzenesulfonate
• 英文别名: butyl 4-nitrobenzenesulfonate
• CAS: 4028-52-8
• 化学式: C₁₀H₁₃NO₅S
• 分子量: 259.283
• InChiKey: ADYUOCBPFNUGDX-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C
• 沸点：
  393.8±25.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 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：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2905199090

反应信息

• 作为反应物：
  描述：

  4-硝基苯磺酸正丁酯 在 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 生成 正溴丁烷
  参考文献：
  名称：

  胶束对卤离子Sn2反应速率的影响

  摘要：

  DOI：

  10.1021/j100384a046
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 正丁醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以82%的产率得到4-硝基苯磺酸正丁酯
  参考文献：
  名称：

  部分氟化的N-烷基取代的哌啶-2-羧酰胺对药理学性质的影响

  摘要：

  通过选择性地将1-3个氟原子引入n-丙基和n中，研究了N-烷基-哌啶-2-羧酰胺的药理相关特性的调节局部麻醉药罗哌卡因和左旋布比卡因的叔丁基侧链。附近氟取代基对碱的调节本质上是加和的，并且表现出随氟与碱中心之间的拓扑距离而变的指数衰减。中性哌啶衍生物的固有亲脂性显示出对连接至中性杂芳基系统的部分氟化烷基的特征响应。但是，附近的氟取代基引起的碱度降低会影响中性pH值的亲脂性，因此所有部分氟化的衍生物的亲脂性都比其未氟化的母体相似或更高。发现水溶性与亲脂性成反比，并且与晶体堆积能有很大关系，如熔点温度的变化所示。发现所有氟化衍生物在人肝微粒体中都更容易被氧化，降解速率与亲脂性增加相关。因为哌啶-2-羧酰胺核心是手性的，所以与对映异构体配对N-烷基是非对映异构的。虽然对于碱性或亲脂性几乎观察不到对这种立体异构的反应，但是对于熔点温度和氧化降解观察到更明显的变化。

  DOI：

  10.1002/cmdc.201600325

文献信息

• Nucleophilicity of halide ions in the micellar pseudophase
  作者：Hamad A. Al-Lohedan

  DOI：10.1016/s0040-4020(01)80038-7

  日期：1989.1

  The reaction of Br− or Cl− with both n-butyl-4-nitrobenzenesulfonate and n-butyl-4-bromobenzenesulfonate 1a and 1b respectively is catalyzed by cationic micelles of cetyltrimethylammonium chloride or bromide (CTACl or CTABr respectively). The increase of rate constant with [surfactant] can be analyzed in terms of the concentration of substrate (1a - b) and halide ion in the micellar pseudophase, and

  BR的反应-或Cl -与两个正丁基-4-硝基苯磺酸酯和正丁基-4-溴苯磺酸1a和1b分别是由十六烷基三甲基氯化铵或溴化铵阳离子胶束（CTACl或CTABr分别）催化。可以根据胶束假相中底物（1a-b）和卤离子的浓度分析[表面活性剂]速率常数的增加，胶束和水假相中的二级速率常数相似。
• Nucleophilicity of azide ion in the micellar pseudophase
  作者：Hamad A.Al-Lohedan

  DOI：10.1016/s0040-4020(01)81527-1

  日期：1990.1

  The reaction of azide ion with 2-chloro-3,5-dinitropyrldine, n-butyl-4-nitrobenzenesulfonate and n-butyl-4-bromobenzenesulfonate is catalyzed by cationic micelles of cetyltrimethylammonium salt (CTAX, X=Cl-, Br-, 0.5 SO=4, OMes, N-3) The second-order rate constants in the micellar pseudophase is smaller than that in water.

  叠氮化物离子与2-氯-3,5-二dinitropyrldine，正丁基-4-硝基苯磺酸酯和正丁基-4-溴苯磺酸是由十六烷基三甲基盐的阳离子胶束催化（CTAX，将反应X =氯- ，溴- ，0.5 SO = 4，OMes，N - 3）胶束假相中的二级速率常数小于水中的二级速率常数。
• ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters
  作者：Fatemeh Tamaddon、Mohammad Reza Sabeti、Abbas Ali Jafari、Farhang Tirgir、Elham Keshavarz

  DOI：10.1016/j.molcata.2011.09.010

  日期：2011.12

  Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity. (C) 2011 Elsevier B.V. All rights reserved.
• Al-Lohedan, Hamad A., Journal of the Chemical Society. Perkin transactions II, 1995, # 8, p. 1707 - 1714
  作者：Al-Lohedan, Hamad A.

  DOI：——

  日期：——
• Inscribing the Perimeter of the PagP Hydrocarbon Ruler by Site-Specific Chemical Alkylation
  作者：M. Adil Khan、Joel Moktar、Patrick J. Mott、Mary Vu、Aaron H. McKie、Thomas Pinter、Fraser Hof、Russell E. Bishop

  DOI：10.1021/bi1011496

  日期：2010.10.26

  The Escherichia coli outer membrane phospholipid:lipid A palmitoyltransferase PagP selects palmitate chains using its beta-barrel-interior hydrocarbon ruler and interrogates phospholipid donors by gating them laterally through an aperture known as the crenel. Lipid A palmitoylation provides antimicrobial peptide resistance and modulates inflammation signaled through the host TLR4/MD2 pathway. Gly88 substitutions can raise the PagP hydrocarbon ruler floor to correspondingly shorten the selected acyl chain. To explore the limits of hydrocarbon ruler acyl chain selectivity, we have modified the single Gly88Cys sulfhydryl group with linear alkyl units and identified C10 as the shortest acyl chain to be efficiently utilized. Gly88Cys-S-ethyl, S-n-propyl, and S-n-butyl PagP were all highly specific for C12, C11, and C10 acyl chains, respectively, and longer aliphatic or aminoalkyl substitutions could not extend acyl chain selectivity any further. The donor chain length limit of C10 coincides with the phosphatidylcholine transition from displaying bilayer to micellar properties in water, but the detergent inhibitor lauryldimethylamine At-oxide also gradually became ineffective in a micellar assay as the selected acyl chains were shortened to C10. The Gly88Cys-S-ethyl and norleucine substitutions exhibited superior C12 acyl chain specificity compared to that of Gly88Met PagP, thus revealing detection by the hydrocarbon ruler of the Met side chain tolerance for terminal methyl group gauche conformers. Although norleucine substitution was benign, selenomethionine substitution at Met72 was highly destabilizing to PagP. Within the hydrophobic and van der Waals-contacted environment of the PagP hydrocarbon ruler, side chain flexibility, combined with localized thioether-aromatic dispersion attraction, likely influences the specificity of acyl chain selection.