N-(4-nitrobenzylidene)-β-naphthylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-nitrobenzylidene)-β-naphthylamine
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: KWECTSUSEYMVLE-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.5
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-nitrobenzylidene)-β-naphthylamine 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 1.08h， 生成 1-methyl-3-(4-nitrophenyl)benzo[f]quinoline
  参考文献：
  名称：

  Kozlov; Sauts; Gusak, Russian Journal of Organic Chemistry, 2000, vol. 36, # 4, p. 531 - 538

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲醛 、 2-萘胺 在 fly-ash:PTS 作用下， 以 neat (no solvent) 为溶剂， 以85%的产率得到N-(4-nitrobenzylidene)-β-naphthylamine
  参考文献：
  名称：

  Solvent-free synthesis of azomethines, spectral correlations and antimicrobial activities of some E-benzylidene-4-chlorobenzenamines

  摘要：

  一些偶氮甲碱，包括取代苄叉-4-氯苯胺（E-亚胺），已在无溶剂条件下通过飞灰：PTS催化的微波辅助缩合4-氯苯胺和取代苯甲醛合成。亚胺的产率已发现超过85%。所有亚胺的纯度已通过其物理常数以及紫外、红外和核磁共振光谱数据进行检查。这些光谱数据已通过单一和多元线性回归分析与Hammett取代常数以及F和R参数相关联。从统计分析的结果中，研究了取代基对上述光谱数据的影响。所有亚胺的抗菌活性已采用标准方法进行研究。

  DOI：

  10.4314/bcse.v29i2.10

文献信息

• Synthesis of benzo[f]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene
  作者：V. I. Grachek

  DOI：10.1007/s11176-005-0094-4

  日期：2004.11

  N -Arylmethylene-2-naphthylamines react with acetylcyclohexane and 1-acetylcyclohexene under mild conditions to afford 2-aryl-2-(2-naphthylamino)ethyl cyclohexyl and 1-cyclohexenyl ketones, respectively. Under more severe conditions (110°C), the reaction is accompanied by cyclization with formation of 3-aryl-1-cyclohexyl(or 1-cyclohexenyl)benzo[ f ]quinolines. Proper choice of the amount of catalyst

  N- 芳基亚甲基-2-萘胺在温和条件下与乙酰基环己烷和1-乙酰基环己烯反应，分别得到2-芳基-2-（2-萘基氨基）乙基环己基和1-环己烯基酮。在更苛刻的条件下（110℃），反应伴随环化，形成3-芳基-1-环己基（或1-环己烯基）苯并[ f ]喹啉。催化剂，温度和反应时间的量的适当选择允许中间体3-芳基-1-环己基（或1-环己烯基）-3,4-二氢苯并[隔离 ˚F 〕喹啉。
• Mercuration of Schiff bases of substituted benzylideneanilines
  作者：Kuiling Ding、Yangjie Wu、Hongwen Hu、Lianfang Shen、Xin Wang

  DOI：10.1021/om00059a058

  日期：1992.11

  As part of an effort to investigate substituent effects on the intramolecular coordination between N and Hg, the mercuration of 36 substituted benzylideneanilines was studied. The structure characterization of the products by IR, H-1 NMR, C-13 NMR, and MS indicates that for all of the reactions examined, the mercury is directed to the ortho position of the N-phenyl ring or the para position of the N-phenyl ring when these sites are not occupied by a substituent. The position of the HgCl group in the mercurated product of N-(4-nitrobenzylidene)-beta-naphthylamine has been confirmed by single-crystal X-ray determination, which also provided circumstantial evidence for the existence of the N--> Hg intramolecular coordination with a four-membered ring. The possible mechanism of the reaction was proposed, in which the mercuration at the ortho position of the N-phenyl ring was facilitated by the imino moiety upon formation of a coordination complex with Hg(OAc)2 in the first step, followed by a subsequent electrophilic substitution at the ortho position of the N-phenyl ring. This reaction is different from the metalation of benzylideneanilines by transition metals, in which the metal atom is usually directed to the ortho position of the C-phenyl ring, and provides a new example of the so-called 'cyclometalation" reaction.
• Kozlov; Popova, Russian Journal of Organic Chemistry, 1999, vol. 35, # 4, p. 603 - 605
  作者：Kozlov、Popova

  DOI：——

  日期：——
• Kozlov; Yakubovich; Murashko, Russian Journal of Organic Chemistry, 2000, vol. 36, # 6, p. 777 - 780
  作者：Kozlov、Yakubovich、Murashko

  DOI：——

  日期：——
• β-oxoacids esters in the synthesis of benzo[f]quinoline derivatives
  作者：K. N. Gusak、N. G. Kozlov

  DOI：10.1134/s1070428007050119

  日期：2007.5

  Condensation of ethyl acetoacetate and ethyl 3-oxo-3-(2-furyl-, 2-quinolyl-, 3-pyridyl)propanoates with azomethines of 2-naphthylamine series led to the formation of ethyl (3-arylbenzo[f]quinol-1-yl)acetates and of esters of the corresponding 3-aryl-1-heteryl-2-benzo[f]quinolylcarboxylic acids. The intermediate reaction products were isolated: ethyl 5-(2-naphthylamino)-3-oxo-5-phenylpentanoate, 2-[(aryl)(2-naphthylamino)methyl]-3-heteryl-3-oxopropanoates, dihydro and tetrahydro derivatives of benzoquinolylacetic and benzoquinolinecarboxylic acids.