5-(2,4-dinitrobenzenesulfenyl)pyrrole-2-carboxaldehyde | 18159-26-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(2,4-dinitrobenzenesulfenyl)pyrrole-2-carboxaldehyde
• 英文别名: 2-<2,4-Dinitro-phenylmercapto>-pyrrol-5-carbaldehyd；5-(2,4-dinitrophenyl)sulfanyl-1H-pyrrole-2-carbaldehyde
• CAS: 18159-26-7
• 化学式: C₁₁H₇N₃O₅S
• 分子量: 293.26
• InChiKey: ZYNHONAAGRIGRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  150
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,4-dinitrobenzenesulfenyl)pyrrole-2-carboxaldehyde 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到5-(2,4-dinitrobenzenesulfinyl)pyrrole-2-carboxaldehyde
  参考文献：
  名称：

  Asymmetric oxidation of 2-(arylsulfenyl)pyrroles

  摘要：

  研究了手性 2-(芳基亚磺酰基)吡咯的不对称氧化。底物中明显的电子效应极大地影响了所获得的对映体选择性，使用 Ti(i-PrO)4/(+)-(R,R)-DET/H2O/CHP 对 5-(硝基苯磺酰基)吡咯-2-甲醛获得了极高的对映体选择性。这一结果预示着可以优化其他二芳基硫化物的不对称氧化，这些底物以前只给出较低的对映体过量。

  DOI：

  10.1139/v08-054
• 作为产物：
  描述：

  2-(2,4-dinitrobenzenesulfenyl)pyrrole 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 sodium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 以67%的产率得到5-(2,4-dinitrobenzenesulfenyl)pyrrole-2-carboxaldehyde
  参考文献：
  名称：

  Comparison of Benzene, Nitrobenzene, and Dinitrobenzene 2-Arylsulfenylpyrroles

  摘要：

  [GRAPHICS]The effectiveness of the 2,4-dinitrobenzenesulfenyl and 4-nitrobenzenesulfenyl groups as masking and directing groups at the 2-position of pyrrole has been investigated and compared to that of 2-phenylthiopyrrole. The presence of the nitro group(s) enhances Stability of the corresponding pyrrole toward acid and does not significantly decrease the ability of the pyrrolic unit to undergo electrophilic aromatic substitution reactions in the form of formylation, nitration, and condensation, with aldehydes. The synthetic utility of 2-(2,4-dinitrobenzenesul.fenyl)pyrrole was demonstrated through the. synthesis of meso-substituted dipyrromethanes. The sulfoxides 2-(2,4-dinitrobenzenesulfinyl)pyrrole and 2-(4-nitrobenzenesulfinyl)pyrrole underwent neither formylation nor nitration, and the increasing presence of nitro groups within the moiety at the 2-position resulted in decreased stability under acidic conditions.

  DOI：

  10.1021/jo070493r

文献信息

• Asymmetric oxidation of 2-(arylsulfenyl)pyrroles
  作者：Alison Thompson、Jose R Garabatos-Perera、H Martin Gillis

  DOI：10.1139/v08-054

  日期：2008.7.1

  The asymmetric oxidation of prochiral 2-(arylsulfenyl)pyrroles has been investigated. A marked electronic effect within the substrate significantly influenced the degree of enantioselectivity obtained, with very high enantio selectivity being obtained for 5-(nitrobenzensulfenyl)pyrrole-2-carboxaldehydes using Ti(i-PrO)₄/(+)-(R,R)-DET/H₂O/CHP. This result bodes well for optimizing the asymmetric oxidation of other diaryl sulfides, substrates that have previously given only low enantiomeric excesses.Key words: asymmetric oxidation, sulfide, sulfoxide, pyrrole.

  研究了手性 2-(芳基亚磺酰基)吡咯的不对称氧化。底物中明显的电子效应极大地影响了所获得的对映体选择性，使用 Ti(i-PrO)4/(+)-(R,R)-DET/H2O/CHP 对 5-(硝基苯磺酰基)吡咯-2-甲醛获得了极高的对映体选择性。这一结果预示着可以优化其他二芳基硫化物的不对称氧化，这些底物以前只给出较低的对映体过量。
• Comparison of Benzene, Nitrobenzene, and Dinitrobenzene 2-Arylsulfenylpyrroles
  作者：Jose R. Garabatos-Perera、Benjamin H. Rotstein、Alison Thompson

  DOI：10.1021/jo070493r

  日期：2007.9.1

  [GRAPHICS]The effectiveness of the 2,4-dinitrobenzenesulfenyl and 4-nitrobenzenesulfenyl groups as masking and directing groups at the 2-position of pyrrole has been investigated and compared to that of 2-phenylthiopyrrole. The presence of the nitro group(s) enhances Stability of the corresponding pyrrole toward acid and does not significantly decrease the ability of the pyrrolic unit to undergo electrophilic aromatic substitution reactions in the form of formylation, nitration, and condensation, with aldehydes. The synthetic utility of 2-(2,4-dinitrobenzenesul.fenyl)pyrrole was demonstrated through the. synthesis of meso-substituted dipyrromethanes. The sulfoxides 2-(2,4-dinitrobenzenesulfinyl)pyrrole and 2-(4-nitrobenzenesulfinyl)pyrrole underwent neither formylation nor nitration, and the increasing presence of nitro groups within the moiety at the 2-position resulted in decreased stability under acidic conditions.