C-(3-methoxyphenyl)-N-tert-butylnitrone | 115995-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: C-(3-methoxyphenyl)-N-tert-butylnitrone
• 英文别名: (Z)-N-tert-butyl-1-(3-methoxyphenyl)methanimine oxide；N-tert-butyl-1-(3-methoxyphenyl)methanimine oxide
• CAS: 115995-22-7
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: ZBJJUMNAPGXIHW-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenylcarbonyloxy radical 、 C-(3-methoxyphenyl)-N-tert-butylnitrone 以 苯 为溶剂， 反应 0.05h， 生成
  参考文献：
  名称：

  Abe, Yukino; Seno, Shin-ya; Sakakibara, Kazuhisa, Journal of the Chemical Society. Perkin transactions II, 1991, # 6, p. 897 - 903

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-2-硝基丙烷 、 3-甲氧基苯甲醛 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以76%的产率得到C-(3-methoxyphenyl)-N-tert-butylnitrone
  参考文献：
  名称：

  Synthesis and characterization of phenyl-substituted C-phenyl-N-tert-butylnitrones and some of their radical adducts

  摘要：

  Synthesis of C-phenyl-N-tert-butylnitrone (PBN) and several of its analogues with substituents in the 2-, 3-, or 4-position on the phenyl ring is described. While a one-pot reduction/condensation method proved suitable for most compounds, it was necessary to prepare some examples by direct condensation or through oxidation of the appropriate imine. The H-1 NMR data for the 3-X- and 4-X-PBN's can be correlated with the Hammett equation. For the 3-X series DELTA-delta for the alpha-proton correlates best with sigma(+) and has a correlation coefficient of 0.90. For the 4-X series a dual substituent parameter equation using sigma(R)0 gives the best correlation with r = 0.99. The hyperfine splitting constants (hfsc's) of the HO. and HOO. adducts of several substituted PBN's are also included and their correlation with the Hammett equation is discussed.

  DOI：

  10.1021/jo00035a020

文献信息

• Palladium-catalyzed C–H Alkenylation of <i>C</i>-Aryl Nitrones
  作者：Megumi Hasegawa、Arisa Nomoto、Takuya Suga、Takahiro Soeta、Yutaka Ukaji

  DOI：10.1246/cl.160821

  日期：2017.1.5

  Palladium-catalyzed C–H alkenylation of C-aryl N-t-butyl nitrones with ethyl acrylate produced ortho-alkenylated benzamide derivatives via isomerization of the nitrone moiety. The use of 1,1,1,3,3,3-hexafluoro-2-propanol/acetic acid as a solvent resulted in effective C–H alkenylation, while competitive 1,3-dipolar cycloaddition was completely suppressed.

  钯催化的 C-芳基 N-叔丁基硝酮与丙烯酸乙酯的 C-H 烯基化通过硝酮部分的异构化产生邻烯基化的苯甲酰胺衍生物。使用 1,1,1,3,3,3-六氟-2-丙醇/乙酸作为溶剂导致有效的 C-H 烯基化，同时完全抑制了竞争性 1,3-偶极环加成。
• Iridium(III)-Catalyzed C–H Amidation of Nitrones with Dioxazolones
  作者：Xia Mi、Weisheng Feng、Chao Pi、Xiuling Cui

  DOI：10.1021/acs.joc.9b00300

  日期：2019.5.3

  efficiently achieved through Ir(III)-catalyzed direct C–H amidation of nitrones with good to excellent yields and tolerance of broad functional groups. This reaction smoothly proceeded at room temperature in the absence of acid or base in a short reaction time. Carbon dioxide was generated as the sole byproduct, thus providing an environmentally benign amidation process. The title products could be efficiently

  通过Ir（III）催化的硝基甲烷的直接C–H酰胺化反应，可以高效地获得各种酰胺化的硝酮，并具有良好至优异的收率和宽泛的官能团耐受性。该反应在短时间内在室温下在不存在酸或碱的条件下平稳地进行。产生二氧化碳作为唯一的副产物，因此提供了对环境无害的酰胺化过程。标题产物可以有效地转化为取代的苯并异恶唑啉。
• Substituent effects on ESR parameters of α-phenyl-N-tert-butylnitrone spin adducts. Resolution enhancement and mass spectrometry
  作者：Kai Pan、Chiou-Rong Lin、Tong-Ing Ho

  DOI：10.1002/mrc.1260310705

  日期：1993.7

  The combination of high‐performance liquid chromatography (HPLC) and ESR spectrometry was used to isolate the free radicals produced by the reaction of a Grignard reagent with 15 substituted α‐Phenyl‐N‐tert‐butylnitrone. Long‐range hyperfine splitting constants (hfsc) were obtained by the resolution enhancement method. Linear correlation studies between hfsc and Hammett σp constants are reported. Dual‐parameter

  高效液相色谱 (HPLC) 和 ESR 光谱法相结合，用于分离格氏试剂与 15 取代的 α-苯基-N-叔丁基硝酮反应产生的自由基。通过分辨率增强方法获得长程超精细分裂常数（hfsc）。报告了 hfsc 和 Hammett σp 常数之间的线性相关性研究。还研究了使用 σR 和 σI 的双参数相关性。报告了 HPLC 分离的自旋加合物的质谱及其碎片模式。
• Alpha-aryl-N-alkylnitrones and pharmaceutical compositions containing the same
  申请人：Kelleher A. Judith

  公开号：US20050124691A1

  公开（公告）日：2005-06-09

  Disclosed are novel α-aryl-N-alkylnitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for preventing and/or treating neurodegenerative, autoimmune and inflammatory conditions in mammals and as analytical reagents for detecting free radicals.

  本发明涉及一种新型的α-芳基-N-烷基亚硝基化合物和含有这种化合物的药物组合物。所述组合物可用作治疗哺乳动物神经退行性、自身免疫和炎症疾病的治疗剂，并可用作检测自由基的分析试剂。
• 10.1021/acs.joc.4c00512
  作者：Xing, Jian、Tang, Hong-Yu、Chen, Jing-Lin、Huang, Zheng、Liang, Jun-Jie、Quan, Yao-Sheng、Mao, Jian-Gang

  DOI：10.1021/acs.joc.4c00512

  日期：——

  methodology for the synthesis of nitrones via palladium-catalyzed redox cross-coupling of nitro compounds and alcohols is established. The protocol is a mild, convenient, ligand-free, and scalable synthesis method that can be compatible with various nitro compounds and alcohols. Nitrone is a significant multifunctional platform synthon which can be synthesized directly and efficiently via this tactic from

  建立了一种通过硝基化合物和醇的钯催化氧化还原交叉偶联合成硝酮的新方法。该方案是一种温和、方便、无配体、可扩展的合成方法，可以与各种硝基化合物和醇兼容。硝酮是一种重要的多功能平台合成子，可以通过这种策略从市售且廉价的原材料直接有效地合成。