N-叔丁基-Alpha-苯基硝酮 | 85225-53-2

• 物质功能分类: 化学试剂 - 有机试剂 - 肟
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-叔丁基-Alpha-苯基硝酮
• 中文别名: N-苯亚甲基叔丁胺-N-氧化物；N-叔丁基-а-苯基硝酮；N-叔丁基苯硝酮；N-叔丁基-α-苯基硝酮
• 英文名称: N-tert-butyl-α-phenylnitrone
• 英文别名: Phenyl-N-tert-butylnitrone, (E)-；N-tert-butyl-1-phenylmethanimine oxide
• CAS: 85225-53-2；3376-24-7
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: IYSYLWYGCWTJSG-FMIVXFBMSA-N

物化性质

• 熔点：
  73-74 °C(lit.)
• 沸点：
  283℃
• 密度：
  0.990
• 闪点：
  119℃
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 安全说明：
  S24/25
• 海关编码：
  2925290090

制备方法与用途

生物活性 N-tert-Butyl-α-phenylnitrone 是一种基于硝酮的自由基清除剂，可形成一氧化氮自旋加合物。它能抑制 COX2 的催化活性，并具有有效的 ROS 清除、抗炎、神经保护、抗衰老和抗糖尿病的作用，同时可以穿透血脑屏障。

靶点

• COX-2
• Reactive oxygen species (ROS)

体外研究 N-tert-Butyl-α-phenylnitrone (PBN) 处理（25-100 µM）显著减少了 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPH)-诱导的细胞内 ROS 积累。此外，N-tert-Butyl-α-phenylnitrone 还减弱了 AAPH 诱导的细胞毒性、基质降解和凋亡，并抑制了 AAPH 诱导的 ERK/MAPK 通路激活。N-tert-Butyl-α-phenylnitrone 具有潜在的间盘退变 (IDD) 研究价值。

体内研究 C57Bl/6 小鼠腹腔注射 N-tert-Butyl-α-phenylnitrone（100 mg/kg，每日两次）不仅消除了脂质过氧化、硝酪氨酸残留和 GSH 耗竭，还减少了外部畸形的发生率。

用途 一种自旋捕集剂，也是 COX-2 抑制剂。

反应信息

• 作为反应物：
  描述：

  N-叔丁基-Alpha-苯基硝酮 在 phosphate buffer 、 维生素 C 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 N-tert-butyl-N-(1-phenylethyl)nitroxide
  参考文献：
  名称：

  An ESR and HPLC-EC Assay for the Detection of Alkyl Radicals

  摘要：

  The correlation of lipid peroxidation with release of alkanes (RH) is considered a noninvasive method for the in vivo evaluation of oxidative stress. The formation of RH is believed to reflect a lipid hydroperoxide (LOOH)-dependent generation of alkoxyl radicals (LO.) that undergo, beta -scission with release of alkyl radicals (R-.). Alternatively, R-. could be spin-trapped with a nitrone before the formation of RH and analyzed by ESR. Extracts from the liver and lung of CCl4- and asbestos-treated rats that were previously loaded with nitrones exhibited ESR spectra suggesting the formation of iso-propyl, n-butyl, ethyl, and pentyl radical-derived nitroxides. In biological systems, various nitroxides with indistinguishable ESR spectra could be formed. Hence, experiments with N-tert-butyl-alpha -phenylnitrone (PBN) for spin trapping of R-. were carried out in which the nitroxides formed were separated and analyzed by HPLC with electrochemical detection (EC). The C1-5 homologous series of PBN nitroxides and hydroxylamines were synthesized, characterized by ESR, GC-MS, and HPLC-EC, and used as HPLC standards. For in vivo generation and spin trapping of R-., rats were loaded with CCl4 and PBN. The HPLC-EC chromatograms of liver extracts from CCl4-treated rats demonstrated the formation of both the nitroxide and hydroxylamine forms of PBN/(CCl3)-C-., as well as the formation of a series of unidentified PBN nitroxides and hydroxylamines. However, formation of PBN adducts with retention times similar to these of the PBN/C2-5 derivatives was not observed. In conclusion, we could not correlate the production of PBN-detectable alkyl radicals with the reported CCl4-dependent production Of C1-5 alkanes. We speculate that the major reason for this is the low steady-state concentrations of R-. produced because only a small fraction of LO. undergo,beta -scission to release R-..

  DOI：

  10.1021/tx015507h

文献信息

• Iron-Catalyzed Highly para-Selective Difluoromethylation of Arenes
  作者：Wei-Tai Fan、Yuting Li、Dongjie Wang、Shun-Jun Ji、Yingsheng Zhao

  DOI：10.1021/jacs.0c09545

  日期：2020.12.9

  bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe(TPP)Cl]-enabled, selective, C-H difluoromethylation of arenes using BrCF2CO2Et as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only

  仅通过改变催化剂体系在间位或对位直接官能化 CH 键是一项重大挑战。我们在此报告了使用 BrCF2CO2Et 作为二氟甲基化源的 [Fe(TPP)Cl] 启用的、选择性的、CH 二氟甲基化芳烃，这成功地改变了从间位到对位的选择性。初步的机理研究表明，铁卟啉配合物不仅激活了芳环，而且由于配体空间的影响，还诱导了对位选择性。
• Drug Resistance Reversal In Neoplastic Disease
  申请人：Patil Ghanshyam

  公开号：US20080200405A1

  公开（公告）日：2008-08-21

  The present invention is directed to compounds, compositions, and methods for halting or reversing the effects of chemoresistance in neoplastic diseases. In particular the use of hydroxylamines is described.

  本发明涉及用于阻止或逆转肿瘤性疾病化疗耐药效应的化合物、组合物和方法。具体描述了羟胺的使用。
• [EN] REGULATORS FOR CONTROLLING LINEAR AND PSEUDO-RING EXPANSION POLYMERIZATION OF VINYL MONOMERS<br/>[FR] RÉGULATEURS POUR RÉGULER LA POLYMÉRISATION LINÉAIRE ET PAR EXPANSION DE PSEUDO-CYCLES DE MONOMÈRES VINYLIQUES
  申请人：DISPOLTEC B V

  公开号：WO2017076992A1

  公开（公告）日：2017-05-11

  The invention concerns new regulator compounds for a novel polymerization process for vinyl monomers, which yields polymers with improved control over composition and nearly full to full conservation of architectural integrity up to high conversion. The regulator compounds are defined by according to anyone of the Formulas (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H) and (1I), wherein R1 stands for an optionally substituted secondary or tertiary alkyl or secondary or tertiary aralkyl; Z1 stands for -CN or a carboxylic acid ester of formula C(O)OR21; Z2 may be chosen from the group of -CN, carboxylic acid, salts of carboxylic acids, carboxylic acid ester, carboxylic acid amides, (hetero)aryl, alkenyl and halogen; R2, R3, R4 and R5 are each independently chosen from the group of H, alkyl, aralkyl, (hetero)aryl, -CN and carboxylic acid ester of formula C(O)OR22; R7 stands for a primary alkyl or primary aralkyl, -CN or hydrogen; Y stands for a bridging group and n is 2, 3, 4, 5 or 6; in case R1 stands for tertiary alkyl or tertiary aralkyl, R6 stands for a primary alkyl or primary aralkyl, -CN or a carboxylic acid ester of formula C(O)OR26; in case R1 stands for a secondary alkyl or secondary aralkyl, R6 stands for a primary or secondary alkyl or primary or secondary aralkyl, -CN, a carboxylic acid ester of formula C(O)OR26 or a phosphonic acid ester of formula P(O)(OR27)2, a (hetero)aryl or an alkenyl; R21, R22, R26 and R27 each independently stand for alkyl or aralkyi having from 1-30 carbon atoms, optionally containing heteroatoms.

  该发明涉及一种用于乙烯单体的新型聚合过程的调节剂化合物，该过程产生具有改善的组成控制和在高转化率下几乎完全至完全保持结构完整性的聚合物。调节剂化合物根据以下任一式(1A)、(1B)、(1C)、(1D)、(1E)、(1F)、(1G)、(1H)和(1I)中的任一式定义，其中R1代表可选择地取代的二级或三级烷基或二级或三级芳基烷基；Z1代表-CN或具有C(O)OR21式的羧酸酯；Z2可从-CN、羧酸、羧酸盐、羧酸酯、羧酸酰胺、(杂)芳基、烯基和卤素的群中选择；R2、R3、R4和R5分别独立地选择自H、烷基、芳基烷基、(杂)芳基、-CN和具有C(O)OR22式的羧酸酯的群；R7代表初级烷基或初级芳基、-CN或氢；Y代表桥接基，n为2、3、4、5或6；如果R1代表三级烷基或三级芳基，则R6代表初级烷基或初级芳基、-CN或具有C(O)OR26式的羧酸酯；如果R1代表二级烷基或二级芳基，则R6代表初级或二级烷基或初级或二级芳基、-CN、具有C(O)OR26式的羧酸酯或具有P(O)(OR27)2式的膦酸酯、(杂)芳基或烯基；R21、R22、R26和R27各自独立地代表具有1-30个碳原子的烷基或芳基，可选择地含有杂原子。
• HYDROXYLAMINE COMPOUNDS AND METHODS OF THEIR USE
  申请人：Patil Ghanshyam

  公开号：US20080280890A1

  公开（公告）日：2008-11-13

  The present disclosure provides compounds that include hydroxylamines of formula I or II, pharmaceutical compositions, and methods for their use. The methods utilize hydroxylamine compounds and/or their pharmaceutical compositions for the treatment of angiogenesis, hepatitis, complement-mediated pathologies, drusen-mediated pathologies, macular degeneration and certain other ophthalmic conditions, inflammation, arthritis, and related diseases and for the inhibition of complement activation.

  本公开提供了包括式I或II的羟胺化合物、制药组合物以及它们的使用方法。该方法利用羟胺化合物及/或其制药组合物治疗血管生成、肝炎、补体介导的病理、色斑介导的病理、黄斑变性和某些其他眼科疾病、炎症、关节炎和相关疾病，并抑制补体激活。
• Regulators for controlling linear and pseudo-ring expansion polymerization of vinyl monomers
  申请人：DISPOLTEC B.V.

  公开号：US10947325B2

  公开（公告）日：2021-03-16

  New regulator compounds for a novel polymerization process for vinyl monomers, which yields polymers with improved control over composition and nearly full to full conservation of architectural integrity up to high conversion. The regulator compounds are defined by according to anyone of the Formulas 1A, 1B, 1C, 1D, 1E, 1F, 1G, 1H and 1I: wherein R1 stands for an optionally substituted secondary or tertiary alkyl or secondary or tertiary aralkyl; Z1 stands for —CN or a carboxylic acid ester of formula C(O)OR21; Z2 may be chosen from the group of —CN, carboxylic acid, salts of carboxylic acids, carboxylic acid ester, carboxylic acid amides, (hetero)aryl, alkenyl and halogen; R2, R3, R4 and R5 are each independently chosen from the group of H, alkyl, aralkyl, (hetero)aryl, —CN and carboxylic acid ester of formula C(O)OR22; R7 stands for a primary alkyl or primary aralkyl, —CN or hydrogen; Y stands for a bridging group and n is 2, 3, 4, 5 or 6; in case R1 stands for tertiary alkyl or tertiary aralkyl, R6 stands for a primary alkyl or primary aralkyl, —CN or a carboxylic acid ester of formula C(O)OR26; in case R1 stands for a secondary alkyl or secondary aralkyl, R6 stands for a primary or secondary alkyl or primary or secondary aralkyl, —CN, a carboxylic acid ester of formula C(O)OR26 or a phosphonic acid ester of formula P(O)(OR27)2, a (hetero)aryl or an alkenyl; R21, R22, R26 and R27 each independently stand for alkyl or aralkyl having from 1-30 carbon atoms, optionally containing heteroatoms.

  用于乙烯基单体新型聚合工艺的新型调节剂化合物，该工艺生产的聚合物可改善对成分的控制，并在高转化率条件下几乎完全保持结构的完整性。这些调节剂化合物是根据公式 1A、1B、1C、1D、1E、1F、1G、1H 和 1I 中的任何一个公式定义的： 其中 R1 代表任选取代的仲或叔烷基或仲或叔烷基；Z1 代表-CN 或式 C(O)OR21 的羧酸酯；Z2 可选自-CN、羧酸、羧酸盐、羧酸酯、羧酸酰胺、（杂）芳基、烯基和卤素；R2、R3、R4 和 R5 各自独立地选自 H、烷基、芳基、（杂）芳基、-CN 和式 C(O)OR22 的羧酸酯组；R7 代表伯烷基或伯芳基、-CN 或氢；如果 R1 代表叔烷基或叔芳烷基，R6 代表伯烷基或伯芳烷基、-CN 或式 C(O)OR26 的羧酸酯；R1代表仲烷基或仲烷基，R6代表伯烷基或仲烷基或伯烷基或仲烷基、-CN、式C(O)OR26的羧酸酯或式P(O)(OR27)2的膦酸酯、（杂）芳基或烯基；R21、R22、R26和R27各自独立地代表具有1-30个碳原子的烷基或芳烷基，可选择含有杂原子。