N-ethyl-3-nitro-5-tert-butylsalicylaldimine | 147820-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-ethyl-3-nitro-5-tert-butylsalicylaldimine
• 英文别名: N-(5-nitro-2-hydroxybenzylidene)ethylamine；N-(5-nitrosalicylidene)-ethylamine；2-(ethyliminomethyl)-4-nitrophenol
• CAS: 147820-72-2
• 化学式: C₉H₁₀N₂O₃
• 分子量: 194.19
• InChiKey: KTRACJXYMVAYHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-ethyl-3-nitro-5-tert-butylsalicylaldimine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 2-[(乙基氨基)甲基]-4-硝基苯酚
  参考文献：
  名称：

  Yoshikawa, Hiromichi; Ueno, Ryohei, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 9, p. 1467 - 1469

  摘要：

  DOI：
• 作为产物：
  描述：

  乙胺 、 5-硝基水杨醛 以 乙醇 为溶剂， 以87%的产率得到N-ethyl-3-nitro-5-tert-butylsalicylaldimine
  参考文献：
  名称：

  Ukhin, L. Yu.; Komissarov, V. N.; Korobov, M. S., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 2.2, p. 331 - 335

  摘要：

  DOI：

文献信息

• ——
  作者：L. Yu. Ukhin、L. V. Belousova、Zh. I. Orlova、S. V. Shishkina、O. V. Shishkin

  DOI：10.1023/a:1020956614588

  日期：——

  The reactions of aminals, the Mannich bases, and azomethines derived from substituted salicylaldehydes were studied. Derivatives of tetrahydrocyclopenta[b]- and hexahydro-cyclohepta[b]chromenes and substituted 2,2'-spirobichromenes were prepared from aminals, and substituted hexahydroxanthenes were synthesized from the Mannich bases. Azomethine derivatives of 5-nitrosalicylaldehyde and aliphatic amines react with cyclohexanone to form 4a-amino-7-nitro-2,3,4,4a-tetrahydro-1H-xanthenes. 4a-Morpholino-7-nitro-9-phenylethynyl-1,2,3,4,9,9a-hexahydroxanthene was studied by X-ray diffraction analysis.
• Hoss, Harald; Elias, Horst, Inorganic Chemistry, 1993, vol. 32, # 3, p. 317 - 323
  作者：Hoss, Harald、Elias, Horst

  DOI：——

  日期：——
• Spectroscopic and theoretical studies of the protonation of N-(5-nitrosalicylidene)-ethylamine
  作者：Krystian Pyta、Piotr Przybylski、Wojciech Schilf、Beata Kołodziej、Anna Szady-Chełmieniecka、Eugeniusz Grech、Bogumil Brzezinski

  DOI：10.1016/j.molstruc.2010.01.002

  日期：2010.4

  The structures of the main tautomers of the Schiff base of salicylaldehyde with ethylamine and its protonated species have been studied by ESI MS, FT-IR as well as H-1, C-13 and N-15 NMR methods. The spectroscopic methods have provided clear evidence that the Schiff base exists in acetonitrile solution in a low barrier O center dot center dot center dot H center dot center dot center dot N imine-oxo tautomeric form. This form is also energetically favourable as indicated by PM5 calculations. This untypical Schiff base form is stabilized by a resonance effect with the nitro group and the interaction of the intramolecular hydrogen-bonded proton with acetonitrile via a intermolecular hydrogen bond. The protonated Schiff base exists in solution as imine-hydroxy form stabilized by intermolecular hydrogen bonds with nitro groups and solvent molecules. (C) 2010 Elsevier B.V. All rights reserved.