(Z)-N-tert-butyl-1-(4-cyanophenyl)methanimine oxide | 67036-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-N-tert-butyl-1-(4-cyanophenyl)methanimine oxide
• 英文别名: C-(4-cyanophenyl)-N-tert-butylnitrone；N-tert-butyl-1-(4-cyanophenyl)methanimine oxide
• CAS: 67036-01-5
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: GVRKCEPOOHMSGH-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-tert-butyl-1-(4-cyanophenyl)methanimine oxide 在 大鼠1,25-二羟基维生素D(1,25(OH)2D)试剂盒 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Greenstock, C. L.; Wiebe, R. H., Canadian Journal of Chemistry, 1982, vol. 60, p. 1560 - 1564

  摘要：

  DOI：
• 作为产物：
  描述：

  4-((tert-butylimino)methyl)benzonitrile 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (Z)-N-tert-butyl-1-(4-cyanophenyl)methanimine oxide
  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

• Single-Step Approach toward Nitrones via Pyridinium Ylides: The DMAP-Catalyzed Reaction of Benzyl Halides with Nitrosoarenes
  作者：Yeonghun Jung、Jee Eun Hong、Jae-Hwan Kwak、Yohan Park

  DOI：10.1021/acs.joc.1c00158

  日期：2021.5.7

  single-step approach is reported for the preparation of nitrones from benzyl halides and nitrosoarenes via pyridinium ylides, utilizing 4-dimethylaminopyridine (DMAP) catalyst and mild reaction conditions (Li2CO3, dimethylacetamide, and room temperature). The reaction provides both keto- and aldonitrones in high yields with a wide scope for benzyl halides and nitrosoarenes. In the same reaction system,

  据报道，采用4-二甲基氨基吡啶（DMAP）催化剂和温和的反应条件（Li 2 CO 3，二甲基乙酰胺和室温）通过吡啶鎓叶立德从苄基卤化物和亚硝基芳烃制备硝酮的一步法。该反应高产率地提供了酮-和醛基酮，并广泛用于苄基卤化物和亚硝基芳烃。在相同的反应系统中，2-甲基-2-亚硝基丙烷，其不具有的芳基，也得到相应的Ñ -叔来自具有吸电子基团的伯苄基溴化物中的-丁基硝酮。作为反应的应用，通过顺序一锅合成，使用2-溴-2-苯基乙酸甲酯制备相应的异恶唑烷。
• 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。
• A novel route to substituted 4-methylene-4,5-dihydroisoxazoles mediated by hafnium(iv) chloride
  作者：Peter J. Dunn、Paul Higginson、Visuvanthar Sridharan、Alison B. Graham、Ronald Grigg、Mark Thornton-Pett

  DOI：10.1039/b105561p

  日期：——

  Heating alkyl vinyl ketones and N-tert-butylarylmethylideneamine N-oxides in the presence of HfCl4 results in the formation of 4-methylene-4,5-dihydroisoxazoles in good yield.

  在 HfCl4 存在下加热烷基乙烯基酮和 N-叔丁基芳基亚甲基胺 N-氧化物，可生成 4-亚甲基-4,5-二氢异噁唑，收率很高。
• NITRONE DERIVATIVES
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0945426A1

  公开（公告）日：1999-09-29

  A compound represented by the figure (1) or a pharmaceutically acceptable salt thereof is useful as a medicament for treating retinal degenerative disorders: wherein Ar is optionally substituted phenyl or optionally substituted heteroaryl;. n is 0, 1 or 2; W is -CH2NH- or -CH=N(O)-; R1, R2 and R3 are independently optionally substituted alkyl, carboxyl or alkoxycarbonyl; any two groups of R1, R2 and R3 may be taken together with the carbon atom to form optionally substituted cycloalkane; all of R1, R2 and R3 may be taken together with the adjusent carbon atom to form optionally substituted bicycloalkane or optionally substituted tricycloalkane; R4 and R5 are independently hydrogen atom or optionally substituted alkyl.

  图（1）所代表的化合物或其药学上可接受的盐可作为治疗视网膜变性疾病的药物： 其中 Ar 是任选取代的苯基或任选取代的杂芳基；. n 是 0、1 或 2； W是-CH2NH-或-CH=N(O)-； R1、R2 和 R3 独立地是任选取代的烷基、羧基或烷氧基羰基；R1、R2 和 R3 中的任意两个基团可与碳原子结合形成任选取代的环烷；所有 R1、R2 和 R3 可与相邻碳原子结合形成任选取代的双环烷或任选取代的三环烷； R4 和 R5 独立地为氢原子或任选取代的烷基。
• Abe, Yukino; Seno, Shin-ya; Sakakibara, Kazuhisa, Journal of the Chemical Society. Perkin transactions II, 1991, # 6, p. 897 - 903
  作者：Abe, Yukino、Seno, Shin-ya、Sakakibara, Kazuhisa、Hirota, Minoru

  DOI：——

  日期：——