2,2,2-trifluoroethyl 4-nitrobenzenesulfonate | 141516-55-4

• 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: 2,2,2-trifluoroethyl 4-nitrobenzenesulfonate
• 英文别名: 2,2,2-Trifluoroethyl 4-nitrobenzene-1-sulfonate
• CAS: 141516-55-4
• 化学式: C₈H₆F₃NO₅S
• mdl: MFCD09863425
• 分子量: 285.201
• InChiKey: NWMYQQUAXHWACZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl 4-nitrobenzenesulfonate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 2,2,2-trifluoroethyl 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：

  2,2,2-三氟乙醇 、 对硝基苯磺酰氯 在 sodium hydroxide 作用下， 反应 0.08h， 以91%的产率得到2,2,2-trifluoroethyl 4-nitrobenzenesulfonate
  参考文献：
  名称：

  SN3-SN2频谱。在水性醇中溶剂分解苯磺酰氯的速率常数和产物选择性

  摘要：

  据报道，在25°C时，苯磺酰氯和4-氯衍生物的溶剂分解反应可在乙醇-水（EW）和甲醇-水（MW）混合物中提供多种二元水性混合物的速率常数和产物选择性（S）。 。使用摩尔浓度将S定义如下：S  ＝（[酯产物] / [酸产物]）×（[水溶剂] / [醇溶剂]）。还报告了4 Z取代的磺酰氯溶剂分解的其他选择性数据（Z = OMe，Me，H，Cl和NO 2）在2,2,2-三氟乙醇水溶液中。为了解释这些结果以及以前发表的有关动力学溶剂同位素效应（KSIE）以及4-硝基和4-甲氧基苯磺酰氯的其他溶剂分解的数据，提出了一种从三阶到二阶变化的机理谱。讨论了这些反应的分子性，以及新术语“ S N 3–S N 2光谱”及其与更完善的术语“ S N 2–S N 1光谱”的联系。版权所有©2009 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1522

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
• 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.
• The S_N3-S_N2 spectrum. Rate constants and product selectivities for solvolyses of benzenesulfonyl chlorides in aqueous alcohols
  作者：T. William Bentley、Robert O. Jones、Dae Ho Kang、In Sun Koo

  DOI：10.1002/poc.1522

  日期：2009.9

  reported for solvolyses of 4‐Z‐substituted sulfonyl chlorides (Z = OMe, Me, H, Cl and NO2) in 2,2,2‐trifluoroethanol–water. To explain these results and previously published data on kinetic solvent isotope effects (KSIEs) and on other solvolyses of 4‐nitro and 4‐methoxybenzenesulfonyl chloride, a mechanistic spectrum involving a change from third order to second order is proposed. The molecularity of

  据报道，在25°C时，苯磺酰氯和4-氯衍生物的溶剂分解反应可在乙醇-水（EW）和甲醇-水（MW）混合物中提供多种二元水性混合物的速率常数和产物选择性（S）。 。使用摩尔浓度将S定义如下：S  ＝（[酯产物] / [酸产物]）×（[水溶剂] / [醇溶剂]）。还报告了4 Z取代的磺酰氯溶剂分解的其他选择性数据（Z = OMe，Me，H，Cl和NO 2）在2,2,2-三氟乙醇水溶液中。为了解释这些结果以及以前发表的有关动力学溶剂同位素效应（KSIE）以及4-硝基和4-甲氧基苯磺酰氯的其他溶剂分解的数据，提出了一种从三阶到二阶变化的机理谱。讨论了这些反应的分子性，以及新术语“ S N 3–S N 2光谱”及其与更完善的术语“ S N 2–S N 1光谱”的联系。版权所有©2009 John Wiley＆Sons，Ltd.