3-formyl-2,2,5,5-tetramethyl-4-phenyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical | 127841-72-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-formyl-2,2,5,5-tetramethyl-4-phenyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical
• CAS: 127841-72-9
• 化学式: C₁₅H₁₈NO₂
• 分子量: 244.313
• InChiKey: HRLQDTFKXNTEEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-formyl-2,2,5,5-tetramethyl-4-phenyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical 在 dimethyl(1-diazo-2-oxopropyl)phosphonate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以34%的产率得到3-ethynyl-2,2,5,5-tetramethyl-4-phenyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical
  参考文献：
  名称：

  具有乙炔基官能团的新型硝基吡咯啉的合成

  摘要：

  摘要 通过顺磁性醛与（1-重氮-2-氧代丙基）膦酸二甲酯（Bestmann-Ohira 试剂）的反应，获得了含有一个或两个乙炔基的 3-取代和 3,4-二取代吡咯啉氮氧化物。发现含有乙炔基的新化合物在 Sonogashira 偶联、环化和环加成反应中是有用的构件，产生潜在的“叠氮基特异性”交联自旋标记、顺磁性配体和多自由基支架。图形概要

  DOI：

  10.1080/00397911.2015.1066391
• 作为产物：
  描述：

  3-bromo-4-formyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-1-oxyl 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3-formyl-2,2,5,5-tetramethyl-4-phenyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical
  参考文献：
  名称：

  顺磁性卤乙烯的钯催化偶联反应

  摘要：

  铃木。顺磁性溴乙烯 1-6 的 Heck 和 Sonogishira 偶联反应得到单官能团 (7a,b)、同双官能团 (8a,b, 24) 和异双官能团氮氧吡咯啉；(9-19, 31) 在温和条件下一步反应。由这些化合物合成硫醇特异性自旋标记物26和28以及吡咯啉氮氧化合物环化杂环30和32。吡咯啉氮氧化合物 33 的乙炔基衍生物也可用作 Larock 吲哚合成中的乙炔反应物，得到顺磁性吲哚衍生物 36。

  DOI：

  10.1055/s-2002-35240

文献信息

• Synthesis and study of new paramagnetic and diamagnetic verapamil derivatives
  作者：Balázs Bognár、Shabnam Ahmed、M. Lakshmi Kuppusamy、Karuppaiyah Selvendiran、Mahmood Khan、József Jekő、Olga H. Hankovszky、Tamás Kálai、Periannan Kuppusamy、Kálmán Hideg

  DOI：10.1016/j.bmc.2010.02.040

  日期：2010.4

  New derivatives of verapamil (1) modified with nitroxides and their precursors were synthesized and screened for reactive oxygen species (ROS)-scavenging activities. The basic structure was modified by changing the nitrile group to an amide or the methyl substituent on tertiary nitrogen with nitroxides and their reduced forms (hydroxylamine and secondary amines). Among the new verapamil derivatives

  合成了用氮氧化合物修饰的维拉帕米 ( 1 ) 的新衍生物及其前体，并筛选了清除活性氧 (ROS) 的活性。通过将腈基团变成酰胺或叔氮上的甲基取代基，用硝基氧及其还原形式（羟胺和仲胺）来修饰基本结构。其中新型维拉帕米衍生物化合物16B [Mohan, IK; 卡恩，M。怀塞尔，S。塞尔文迪兰，K.；斯里达尔，A.；加利福尼亚州卡恩斯；博格纳尔，B.；卡莱，T。希德，K。库普萨米，P. Am。J.生理学。心脏循环。生理。 2009 , 296, 140]，用 2,2,6,6-四甲基-1,2,3,6-四氢吡啶-1-yloxyl 的羟胺盐修饰被证明是体外最好的 ROS 清除剂，并保护 HSMC 和 CHO 细胞免受 H 2 O 2引起的损伤。
• Synthesis and Dehydrobromination of α-Bromo Aldehyde and Ketone Nitroxyl Radical Spin Labels
  作者：H. Olga Hankovszky、Kálmán Hideg、P. Cecilla Sár、M. Judit Lovas、Gyula Jerkovich

  DOI：10.1055/s-1990-26788

  日期：——

  Various types of α-bromo aldehyde and ketone derivatives of nitroxyl radicals can be prepared in a selective bromination reaction with pyrrolidone hydrotribromide in the presence of a double bond. The saturated α-bromo aldehydes are dehydrobrominated with 1,8-diazabicyclo [5,4,0]undec-7-ene.

  在双键存在的情况下，通过与吡咯烷酮氢溴酸盐进行选择性溴化反应，可以制备各种类型的δ-溴醛和酮衍生物。饱和δ±-溴醛与 1,8- 二氮杂双环 [5,4,0]undec-7-ene 发生脱氢溴化反应。
• 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.
• Synthesis of new pyrrolidine nitroxide epoxides as versatile paramagnetic building blocks
  作者：Tamás Kálai、Cecı́lia P. Sár、József Jekő、Kálmán Hideg

  DOI：10.1016/s0040-4039(02)01911-1

  日期：2002.11

  Pyrrolidine nitroxide epoxides were synthesized by oxidation of the corresponding alkene, diene and alpha,beta-unsaturated aldehyde with m-CPBA or H2O2 to provide new spin labels and paramagnetic synthons. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of New Pyrroline Nitroxides with Ethynyl Functional Group
  作者：Györgyi Úr、Tamás Kálai、Mária Balog、Balázs Bognár、Gergely Gulyás-Fekete、Kálmán Hideg

  DOI：10.1080/00397911.2015.1066391

  日期：2015.9.17

  Abstract 3-Substituted and 3,4-disubstituted pyrroline nitroxides containing an ethynyl group or two ethynyl groups were achieved by the reaction of a paramagnetic aldehydes with dimethyl (1-diazo-2-oxopropyl)phosphonate (Bestmann–Ohira reagent). The new compounds containing an ethynyl group were found to be useful building blocks in Sonogashira coupling, cyclization, and cycloaddition reactions producing

  摘要 通过顺磁性醛与（1-重氮-2-氧代丙基）膦酸二甲酯（Bestmann-Ohira 试剂）的反应，获得了含有一个或两个乙炔基的 3-取代和 3,4-二取代吡咯啉氮氧化物。发现含有乙炔基的新化合物在 Sonogashira 偶联、环化和环加成反应中是有用的构件，产生潜在的“叠氮基特异性”交联自旋标记、顺磁性配体和多自由基支架。图形概要