1-{[(3-chlorophenyl)imino]methyl}-2-naphthol | 3172-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-{[(3-chlorophenyl)imino]methyl}-2-naphthol
• 英文别名: 2-Hydroxy-1-naphthalidene-3'-chloroaniline；N-[2-hydroxy-1-naphthaledene]-3-chloroaniline；<3-Chlor-phenylimino>-<2-hydroxy-<1>-naphtyl>-methan；2-Hydroxy-α-naphthyliden-m-chloranilin；1-[(3-Chlor-phenylimino)-methyl]-[2]naphthol；2-hydroxy-1-naphthalidene-3'-chloro-anil；2-Oxy-naphthaldehyd-(1)-(3-chlor-anil)；1-(3-Chlorophenyliminomethyl)-2-naphthol；1-[(3-chlorophenyl)iminomethyl]naphthalen-2-ol
• CAS: 3172-38-1
• 化学式: C₁₇H₁₂ClNO
• mdl: MFCD00021562
• 分子量: 281.741
• InChiKey: NAOHNCHHOYHAPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-{[(3-chlorophenyl)imino]methyl}-2-naphthol 在 sodium perchlorate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以32.9%的产率得到2,2'-{1,2-bis[(3-chlorophenyl)amino]ethane-1,2-diyl}di(1-naphthol)
  参考文献：
  名称：

  Electrochemical behaviour of 1-{[(3-halophenyl)imino]methyl}-2-naphthol Schiff bases on graphite electrodes

  摘要：

  在石墨电极上进行了1-{[(3-卤代苯基)亚甲基]-2-萘酚}化合物的电化学还原研究。所有化合物均溶于四氢呋喃（THF）和甲醇的1:4（体积分数）混合物中。NaClO4（0.1 mol L-1）用作支持电解质。采用循环伏安法、计时安培法、恒电位库仑计量法（体积电解）和恒电位制备电解法。循环伏安数据显示，在石墨上的还原是不可逆的，并遵循EC机制。使用计时安培的Cottrell斜率和超微电极稳态电流确定了扩散系数和转移的电子数。电子数也通过体积电解法确定。电还原产物通过恒电位制备电解法制备毫克量，并通过光谱方法纯化和表征。基于这些发现，提出了电还原过程的机理。关键词：电化学还原，羟基萘亚胺席夫碱，循环伏安，超微电极。

  DOI：

  10.1139/v04-021
• 作为产物：
  描述：

  3-氯苯胺 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 2.0h， 生成 1-{[(3-chlorophenyl)imino]methyl}-2-naphthol
  参考文献：
  名称：

  Prabhu; Dodwad, Journal of the Indian Chemical Society, 1990, vol. 67, # 7, p. 541 - 545

  摘要：

  DOI：

文献信息

• Electron spin resonance spectral studies of vanadyl complexes with some schiff bases
  作者：S.S. Dodwad、R.S. Dhamnaskar、P.S. Prabhu

  DOI：10.1016/s0277-5387(00)80629-4

  日期：1989.1

  Vanadyl complexes with Schiff bases of 2-hydroxy-1-naphthalidene and aryl amines were prepared. The ESR spectra of all the complexes were recorded at room temperature and at liquid nitrogen temperature (177 K), by the method of Kneubuhl, Sands and German. A small polycrystalline sample of the tetracyanoethylene (TCNE) free radical was used as a “g” marker. The spectra were again analysed by the method

  制备具有2-羟基-1-萘的席夫碱和芳基胺的钒基络合物。通过Kneubuhl，Sands和German的方法，在室温和液氮温度（177 K）下记录了所有配合物的ESR光谱。将四氰基亚乙基（TCNE）自由基的少量多晶样品用作“ g ”标记。再次通过Kneubuhl，Sands和Garman的方法分析光谱。获得值xv g xv，g xV（平行），g hu（垂直），xv A xv，A xV，A hu。表达式hv = gβH用于评估“ g”值。由于在室温下溶液中分子迅速翻滚，因此未观察到各向异性，但在177 K下清晰可见。“ g ”是指示共价的功能，因此，据报导了钒基络合物的共价顺序。
• Senier; Clarke, Journal of the Chemical Society, 1911, vol. 99, p. 2082
  作者：Senier、Clarke

  DOI：——

  日期：——
• Prabhu; Dodwad, Journal of the Indian Chemical Society, 1990, vol. 67, # 7, p. 541 - 545
  作者：Prabhu、Dodwad

  DOI：——

  日期：——
• Pardeshi; Palaskar; Chondhekar, Journal of the Indian Chemical Society, 2002, vol. 79, # 12, p. 958 - 959
  作者：Pardeshi、Palaskar、Chondhekar

  DOI：——

  日期：——
• Electrochemical behaviour of 1-{[(3-halophenyl)imino]methyl}-2-naphthol Schiff bases on graphite electrodes
  作者：Kamran Polat、Mustafa Uçar、M Levent Aksu、Hüseyin Ünver

  DOI：10.1139/v04-021

  日期：2004.7.1

  An electrochemical study of the reduction of 1-[(3-halophenyl)imino]methyl}-2-naphthol compounds on graphite electrodes was carried out. All the compounds were dissolved in a 1:4 (volume fraction) mixture of tetrahydrofuran (THF) and methanol. NaClO₄ (0.1 mol L^–1) was used as the supporting electrolyte. Cyclic voltammetry, chronoamperometry, constant-potential coulometry (bulk electrolysis), and constant-potential preparative electrolysis were employed. The cyclic voltammetric data revealed that the reduction on graphite was irreversible and followed an EC mechanism. The diffusion coefficients and the number of electrons transferred were determined using the chronoamperometric Cottrell slope and the ultramicro electrode steady-state current. The number of electrons was also determined by bulk electrolysis. The products of the electroreduction were synthesized in milligram quantities by the use of constant-potential preparative electrolysis. These products were purified and characterized by spectroscopic methods. Based on these findings, a mechanism for the electroreduction process is proposed.Key words: electrochemical reduction, hydroxynaphthylideneaniline Schiff bases, cyclic voltammetry, ultramicro electrode.

  在石墨电极上进行了1-[(3-卤代苯基)亚甲基]-2-萘酚}化合物的电化学还原研究。所有化合物均溶于四氢呋喃（THF）和甲醇的1:4（体积分数）混合物中。NaClO4（0.1 mol L-1）用作支持电解质。采用循环伏安法、计时安培法、恒电位库仑计量法（体积电解）和恒电位制备电解法。循环伏安数据显示，在石墨上的还原是不可逆的，并遵循EC机制。使用计时安培的Cottrell斜率和超微电极稳态电流确定了扩散系数和转移的电子数。电子数也通过体积电解法确定。电还原产物通过恒电位制备电解法制备毫克量，并通过光谱方法纯化和表征。基于这些发现，提出了电还原过程的机理。关键词：电化学还原，羟基萘亚胺席夫碱，循环伏安，超微电极。