2,2,5,5-四甲基-2,5-二氢-1H-吡咯-3-甲醛 | 170810-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 2,2,5,5-四甲基-2,5-二氢-1H-吡咯-3-甲醛
• 英文名称: 3-formyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrole
• 英文别名: 2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carbaldehyde；2,2,5,5-tetramethyl-1H-pyrrole-3-carbaldehyde
• CAS: 170810-86-3
• 化学式: C₉H₁₅NO
• mdl: MFCD18810291
• 分子量: 153.224
• InChiKey: RRYCUZQBGRXPAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,5,5-四甲基-2,5-二氢-1H-吡咯-3-甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 (2E,4E)-N-Methoxy-N,3-methyl-5-(2,2,5,5-tetramethyl-3-pyrrolin-3-yl)-2,4-pentadienamide
  参考文献：
  名称：

  含氮氧化物的多烯的合成：两个化学修饰的视网膜及其与细菌素的相互作用

  摘要：

  描述了两个视网膜类似物的合成和光谱表征，顺磁性的3-吡咯啉-1-基氧基类似物1及其抗磁性等效物3-吡咯啉类似物2。讨论了含氨氧基的多烯的合成的各个方面。与细菌视紫红质相互作用后，蛋白中会同时掺入1和2，并形成一个λmax 459 nm的系统。两种细菌视紫红质类似物都不具有光活性。包含1的系统的ESR光谱数据表明，蛋白质中发色团的环部分牢固地固定在方向上。

  DOI：

  10.1002/recl.19951140906
• 作为产物：
  描述：

  3-formyl-2,2,5,5-tetramethyl-pyrroline-1-oxyl 在 铁粉 、 溶剂黄146 作用下， 反应 3.0h， 以49%的产率得到2,2,5,5-四甲基-2,5-二氢-1H-吡咯-3-甲醛
  参考文献：
  名称：

  将硝酮和氮氧化物选择性还原为官能化仲胺

  摘要：

  摘要 在不同官能团（醛、腈、羧酸酯、活化和未活化的双键或三键）存在下，硝酮和氮氧化合物被 Fe/AcOH 选择性还原为仲胺。

  DOI：

  10.1080/00397919508011423

文献信息

• Synthesis and Reactions of New Nitronyl Nitroxides
  作者：Tamás Kálai

  DOI：10.1055/s-1997-1311

  日期：1997.9

  Various new 2-substituted 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-yloxyl 3-oxide mono- 1b, 7, 13a,b, 14, 15, 16, 17, 22 and biradicals 8, 9 were prepared. The nitronyl nitroxide functions were selectively reduced by Fe/HOAc to 1-hydroxyimidazoline derivatives 3b, 11, 21. The reductions by Zn/HCl led to imidazolines 4, 12. The nitronyl nitroxide functions remained inert when the 2-phenyl compounds was nitrated by H2SO4/HNO3 to give nitrophenyl nitronyl nitroxide derivatives 13a,b, 14.

  合成了多种新型2取代的4,4,5,5-四甲基-4,5-二氢-1H-咪唑-1-氧基3-氧化物单体1b、7、13a、b、14、15、16、17、22以及双自由基8、9。通过Fe/HOAc选择性还原了亚硝基氮氧化物，生成了1-羟基咪唑啉衍生物3b、11、21。使用Zn/HCl还原得到咪唑啉4、12。在用H2SO4/HNO3对2-苯基化合物进行硝化时，亚硝基氮氧化物功能保持惰性，生成了硝基苯亚硝基氮氧化物衍生物13a、b、14。
• LIQUID CRYSTAL COMPOSITION CONTAINING NITROGEN-CONTAINING CYCLIC COMPOUND AND LIQUID CRYSTAL DISPLAY DEVICE
  申请人：JNC CORPORATION

  公开号：US20160208172A1

  公开（公告）日：2016-07-21

  The disclosure shows a liquid crystal composition that contains a compound having an effect of preventing photolysis of the liquid crystal composition and having high solubility in the liquid crystal composition, and that satisfies at least one of characteristics such as high maximum temperature, low minimum temperature, small viscosity, suitable optical anisotropy, large positive or negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light or heat, and a suitable elastic constant, etc. and so on. The disclosure shows a liquid crystal composition that contains a compound having the following azolidine ring (Q-1) or azepane ring (Q-2), a liquid crystal display device and so on.

  该披露显示了一种液晶组合物，其中包含一种化合物，具有防止液晶组合物光解的效果，并在液晶组合物中具有较高的溶解度，并且满足以下特征之一，如高最高温度、低最低温度、粘度小、适当的光学各向异性、大正或负介电各向异性、大特定电阻、对紫外光或热稳定性高，以及适当的弹性常数等。披露显示了一种液晶组合物，其中包含具有以下氮杂环（Q-1）或氮杂环（Q-2）的化合物，液晶显示器件等等。
• New Poly(ADP-ribose) Polymerase-1 Inhibitors with Antioxidant Activity Based on 4-Carboxamidobenzimidazole-2-ylpyrroline and -tetrahydropyridine Nitroxides and Their Precursors
  作者：Tamás Kálai、Mária Balog、Alíz Szabó、Gergely Gulyás、József Jekő、Balázs Sümegi、Kálmán Hideg

  DOI：10.1021/jm801476y

  日期：2009.3.26

  4-Carboxamidobenzimidazoles were previously described as PARP inhibitor compounds. Here we report upon 4-carboxamido-1H-benzimidazoles substituted in the 2-position with nitroxides or their amine or hydroxylamine precursors. Among the new molecules, a highly active PARP inhibitor 4h (IC50 = 14 nM) was identified with antioxidant/radical scavenger activity. We concluded that in most cases sterically hindered amines are better PARP inhibitors than their oxidized form and structural changes in the 2-substituted 4-carboxamido-1H-benzimidazoles (such as N-substitution or changing the position of the carboxamide group) were detrimental to PARP inhibition activity but not to antioxidant activity. These results indicate the advantages of combining an antioxidant nitroxide or nitroxide precursor with a PARP inhibitor molecule to decrease or eliminate the deleterious processes initiated by reactive oxygen and reactive nitrogen species (ROS and RNS). The radical scavenging capability of 4h was demonstrated by EPR study of urine collected after drug administration.
• Studies of Structure−Activity Relationship of Nitroxide Free Radicals and Their Precursors as Modifiers Against Oxidative Damage
  作者：Murali C. Krishna、William DeGraff、Olga H. Hankovszky、Cecília P. Sár、Tamás Kálai、József Jekő、Angelo Russo、James B. Mitchell、Kálmán Hideg

  DOI：10.1021/jm9802160

  日期：1998.8.1

  The protective effects of stable nitroxides, as well as their hydroxylamine and amine precursors, have been tested in Chinese hamster V79 cells subjected to H2O2 exposure at fixed concentration or exposure to ionizing radiation. Cytotoxicity was evaluated by monitoring the viability of the cells assessed by the clonogenic assay. The compounds tested at fixed concentration varied in terms of ring size, oxidation state, and ring substituents. Electrochemical studies were carried out to measure the redox midpoint potentials. The studies show that in the case of protection against H2O2 exposure, the protection was determined by the ring size, oxidation state, and redox midpoint potentials. In general the protection factors followed the order nitroxides > hydroxylamines > amines. Both the six-membered ring nitroxides and substituted five-membered ring nitroxides were efficient protectors. For six-membered ring nitroxides, the compounds exhibiting the lowest midpoint potentials exhibited maximal protection. In the case of X-radiation, nitroxides were the most protective though some hydroxylamines were also efficient. The amines were in some cases found to sensitize the toxicity of aerobic radiation exposure. The protection observed by the nitroxides was not dependent on the ring size. However, the ring substituents had significant influence on the protection. Compounds containing a basic side chain were found to provide enhanced protection. The results in this study suggest that these compounds are novel antioxidants which can provide cytoprotection in mammalian cells against diverse types of oxidative insult and identify structural determinants optimal for protection against individual types of damage.
• Synthesis of paramagnetic BODIPY dyes as new double (spin and fluorescence) sensors
  作者：Tamás Kálai、Éva Hideg、József Jekő、Kálmán Hideg

  DOI：10.1016/j.tetlet.2003.09.107

  日期：2003.11

  Paramagnetic pyrroline and 1,2,3,6-tetrahydropyridine derivatives of BODIPY and their diamagnetic analogs have been synthesized and characterized as novel redox double sensor and cation sensitive reagents. (C) 2003 Elsevier Ltd. All rights reserved.