1-p-toluenesulfonyl-2-nitropyrrole | 128080-58-0

• 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: 1-p-toluenesulfonyl-2-nitropyrrole
• 英文别名: 1-[(4-methylbenzene)sulfonyl]-2-nitro-1H-pyrrole；1-(4-methylphenyl)sulfonyl-2-nitropyrrole
• CAS: 128080-58-0
• 化学式: C₁₁H₁₀N₂O₄S
• 分子量: 266.277
• InChiKey: DYDHHXIHVGYNKP-UHFFFAOYSA-N

物化性质

• 沸点：
  460.0±47.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-p-toluenesulfonyl-2-nitropyrrole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到2-硝基-1H-吡咯
  参考文献：
  名称：

  Total Synthesis of Heronapyrrole C

  摘要：

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.

  DOI：

  10.1021/ol403246j
• 作为产物：
  描述：

  2-硝基-1H-吡咯 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到1-p-toluenesulfonyl-2-nitropyrrole
  参考文献：
  名称：

  五元杂芳族化合物硝基衍生物中氢的取代核亲核取代

  摘要：

  噻吩，呋喃和吡咯的硝基衍生物与含有离去基团的碳负离子反应，生成被官能化的烷基取代基取代氢的产物。讨论了该反应的许多具体特征。

  DOI：

  10.1016/0040-4020(95)00445-e

文献信息

• Vicarious nucleophilic substitution of hydrogen in nitroderivatives of five-membered heteroaromatic compounds
  作者：Mieczyslaw Makosza、Ewa Kwast

  DOI：10.1016/0040-4020(95)00445-e

  日期：1995.7

  Nitro derivatives of thiophene, furan and pyrrole react with carbanions containing leaving groups giving products of replacement of hydrogen with functionalized alkyl substituents. Many specific features of this reaction are discussed.

  噻吩，呋喃和吡咯的硝基衍生物与含有离去基团的碳负离子反应，生成被官能化的烷基取代基取代氢的产物。讨论了该反应的许多具体特征。
• Comparison of the reactivity between 2- and 3-nitropyrroles in cycloaddition reactions. A simple indole synthesis
  作者：Claudia Della Rosa、Maria Kneeteman、Pedro Mancini

  DOI：10.1016/j.tetlet.2006.12.097

  日期：2007.2

  N-Tosyl-2-nitropyrroles react at high temperature with poorly and strongly activated dienes. They exhibit a dienophilic character similar to N-tosyl-3-nitropyrroles producing the corresponding indoles through a classical Diels–Alder process. A similar behaviour was observed in disubstituted N-tosyl-pyrroles.

  N-甲苯磺酰基-2-硝基吡咯在高温下与活化程度较弱的二烯发生反应。它们表现出与N-甲苯磺酰基-3-硝基吡咯类似的双亲性特征，并通过经典的Diels-Alder工艺产生相应的吲哚。在二取代的N-甲苯磺酰基-吡咯中观察到类似的行为。
• Unusual orientation in vicarious nucleophilic substitution of hydrogen in nitropyrroles
  作者：Kwast Ewa、Mieczysław Makosza

  DOI：10.1016/s0040-4039(00)94350-8

  日期：1990.1

  The vicarious nucleophilic substitution of hydrogen in N-substituted 2-nitropyrrole with carbanion of chloromethyl phenyl sulfone occurs at position 5- or 3- depending upon electronic effects of the N-protecting group.

  取决于N-保护基团的电子效应，N-取代的2-硝基吡咯中的氢的取代基被氯甲基苯基砜的碳负离子取代。
• Diels–Alder reactions of N-tosylpirroles developed in protic ionic liquids. Theoretical studies using DFT methods
  作者：Claudia Della Rosa、Carla Ormachea、Maria N. Kneeteman、Claudia Adam、Pedro M.E. Mancini

  DOI：10.1016/j.tetlet.2011.10.017

  日期：2011.12

  N-Tosyl-2-nitropirrole and N-tosyl-3-nitropirrole react with poorly and activated dienes using protic ionic liquids as reaction media. They exhibit a dienophile character producing the corresponding indoles through a Diels-Alder process. In all cases the presence of protic ionic liquids as reaction media improves the yields with respect to use of molecular solvent, while the temperature and the reaction time decrease. Part of this work is specifically concerned with theoretical studies using DFT methods, The global and local electrophilicity and nucleophilicity indices were calculated for the dienophiles and dienes used in this study in order to evaluate reactivity and regioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• KWAST, EWA;MAKOSZA, MIECZYSLAW, TETRAHEDRON LETT., 31,(1990) N, C. 121-122
  作者：KWAST, EWA、MAKOSZA, MIECZYSLAW

  DOI：——

  日期：——