p-Chlorophenyl p-nitrobenzenesulphonate | 128886-84-0

• 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: p-Chlorophenyl p-nitrobenzenesulphonate
• 英文别名: 4-chlorophenyl 4-nitrobenzenesulfonate；4-Nitro-benzenesulfonic acid 4-chloro-phenyl ester；(4-chlorophenyl) 4-nitrobenzenesulfonate
• CAS: 128886-84-0
• 化学式: C₁₂H₈ClNO₅S
• 分子量: 313.718
• InChiKey: ZPIXXIHREKRTLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-Chlorophenyl p-nitrobenzenesulphonate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 4-chlorophenyl 4-(3-(2,6-difluorobenzoyl)ureido)benzenesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Amide and Sulfonate Groups Based on the Sulfonylurea Receptor Protein Binding Site for Diflubenzuron and Glibenclamide

  摘要：

  On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by H-1 nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.

  DOI：

  10.1021/jf304468b
• 作为产物：
  描述：

  对氯苯酚 、 对硝基苯磺酰氯 生成 p-Chlorophenyl p-nitrobenzenesulphonate
  参考文献：
  名称：

  芳基苯磺酸盐与苄胺在乙腈中的亲核取代反应中的竞争性反应途径。

  摘要：

  研究了芳基苯磺酸盐（YC6H4SO2OC6H4Z）与苄胺（XC6H4CH2NH2）在乙腈中于65.0摄氏度下的反应。反应通过SO（kS-O）和CO（kC-O）键分裂而竞争地进行，但前者提供了主要的反应途径。在分析Hammett和Brönsted系数以及交叉相互作用常数rho（XY），rho（YZ）和rho（XZ）的基础上，提出了通过限速形成SO键裂解的逐步机理三角-双锥体五元（TBP-5C）中间体，而CO键断裂则是通过限速从Meisenheimer型络合物中排出磺酸根阴离子（YC6H4SO3-）来进行的。

  DOI：

  10.1021/jo0161835

文献信息

• Evidence for a single transition state in the intermolecular transfer of a sulfonyl group between oxyanion donor and acceptors
  作者：Peter D'Rozario、Richard L. Smyth、Andrew Williams

  DOI：10.1021/ja00329a078

  日期：1984.8

  Etude de la reactivite d'oxyanions vis-a-vis du nitro-4 benzenesulfonate de nitro-4 phenyle

  Etude de la reactive d'oxyanions vis-a-vis du nitro-4 benzosulfonate de nitro-4 phenyle
• Kinetic Study on Alkaline Hydrolysis of Y-substituted Phenyl X-substituted Benzenesulfonates: Effects of Changing Nucleophile from Azide to Hydroxide Ion on Reactivity and Transition-State Structure
  作者：Ji-Hyun Moon、Min-Young Kim、So-Yeop Han、Ik-Hwan Um

  DOI：10.1002/bkcs.10297

  日期：2015.6

  Second‐order rate constants () for alkaline hydrolysis of 2,4‐dinitrophenyl X‐substituted benzenesulfonates (1a–1f) and Y‐substituted phenyl 4‐nitrobezenesulfonates (2a–2g) have been measured spectrophotometrically. Comparison of with the values reported previously for the corresponding reactions with has revealed that OH  is only 103‐fold more reactive than , although the former is 11 pK a units

  用分光光度法测量了2,4-二硝基苯基X-取代的苯磺酸盐（1a-1f）和Y-取代的苯基4-硝基苯磺酸盐（2a-2g）的碱解二级速率常数（）。比较与所述值之前为相应的反应报道显示，OH 只有10 3倍比更具反应性，虽然前者是11个P ķ 一个单位比后者更碱性。汤川-津野情节用于的反应中1A-1F导致具有优异的线性相关ρ X  = 2.09和- [R= 0.41。用于反应中的布朗斯台德型情节2A-2G是线性与β LG  = -0.51，这是典型的反应报告通过协调一致机理进行。汤川-津野情节用于的反应中2A-2G显示出优异的线性度ρ Ŷ  = 1.85和- [R = 0.25，这表明局部负电荷开发上离去基团的在过渡态O原子。因此，已得出结论认为1a-1f和2a-2g的碱性水解是通过协同机制进行的。所述的比较ρ X和β LG用于与反应值 离子表明，与氢氧根离子相比，与氢氧根离子的反应通过更紧密的过渡态结构进行。
• Suh, Junghun; Suh,, Myung Koo; Cho, Seung Ho, Journal of the Chemical Society. Perkin transactions II, 1990, # 5, p. 685 - 688
  作者：Suh, Junghun、Suh,, Myung Koo、Cho, Seung Ho

  DOI：——

  日期：——
• SUH, JUNGHUN;SUH, MYUNG KOO;CHO, SEUNG HO, J. CHEM. SOC. PERKIN TRANS. PT 2,(1990) N, C. 685
  作者：SUH, JUNGHUN、SUH, MYUNG KOO、CHO, SEUNG HO

  DOI：——

  日期：——
• Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Amide and Sulfonate Groups Based on the Sulfonylurea Receptor Protein Binding Site for Diflubenzuron and Glibenclamide
  作者：Ranfeng Sun、Ziwen Wang、Yongqiang Li、Lixia Xiong、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/jf304468b

  日期：2013.1.23

  On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by H-1 nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.