1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone | 77761-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone
• 英文别名: N-(p-Chlor-phenyl)-2-oxo-1.2-dihydro-naphthyliden-(1)-methylamin；(Z)-1-(((4-chlorophenyl)amino)methylene)naphthalen-2(1H)-one；(1Z)-1-[(4-chloroanilino)methylidene]naphthalen-2-one
• CAS: 77761-42-3
• 化学式: C₁₇H₁₂ClNO
• 分子量: 281.741
• InChiKey: MINSLRVCZRUAIN-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-<(4'-chlorophenylimino)methyl>-2-naphthol 以 乙醇 为溶剂， 生成 1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone
  参考文献：
  名称：

  Antonov, Liudmil; Fabian, Walter M.F.; Nedeltcheva, Daniela, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 6, p. 1173 - 1179

  摘要：

  DOI：

文献信息

• Synthesis and Structural Characterization of (Z)-3-[(4-Chlorophenylamino) Methylene] Naphthalene-2(3H)-One: An Enol, Keto or Zwitterionic Tautomer?
  作者：T. K. Venkatachalam、Gregory K. Pierens、Paul V. Bernhardt、Luke Hammond、David C. Reutens

  DOI：10.1007/s10870-011-0022-x

  日期：2011.7

  The structure of the title compound was determined using X-ray crystallography at both 173 and 293 K. The molecular structure and packing did not change significantly with temperature and a disordered structure was identified comprising a keto and enol tautomeric form. Analysis of the bond lengths in the vicinity of the C=O group suggested the keto form was predominantly in its zwitterionic form structure. 1H NMR spectroscopy showed the presence of a single compound in solution with two diagnostic doublets demonstrating the compound had an NH group next to a CH group resembling the zwitterionic form of the compound.

  在173和293 K下，使用X射线晶体学确定了标题化合物的结构。分子结构和堆积方式并未随温度发生显著变化，并确定其为无序结构，由酮和烯醇互变形式组成。对C=O基团附近的键长分析表明，酮形式主要呈两性离子形式结构。1H NMR光谱显示溶液中存在一种单一化合物，其有两个诊断双峰，表明该化合物在CH基团旁边有一个NH基团，类似于该化合物的两性离子形式。
• Eine breit anwendbare Synthese fluoreszierender kondensierter ?-Pyrone
  作者：Otto S. Wolfbeis、Erich Ziegler、Andreas Knierzinger、Helmut Wipfler、Iris Trummer

  DOI：10.1007/bf00938720

  日期：——
• WOLFBEIS O. S.; ZIEGLER E.; KNIERZINGER A.; WIPFLER H.; TRUMMER I., MONATSH. CHEM., 1980, 111, NO 1, 93-112
  作者：WOLFBEIS O. S.、 ZIEGLER E.、 KNIERZINGER A.、 WIPFLER H.、 TRUMMER I.

  DOI：——

  日期：——
• ——
  作者：H. Ünver、M. Kabak、D. Mehmet Zengin、T. Nuri Durlu

  DOI：10.1023/a:1014395132751

  日期：——

  1-[N-(4-chlorophenyl)]aminomethylidene-2(1H)naphthalenone (C17H12NOCl) (1) was synthesized and the crystal structure was determined. Compound I crystallizes in the monoclinic space group P2(1)/n with a = 4.761(3) Angstrom, b = 20.347(1) Angstrom, c = 13.773(2) Angstrom, beta = 92.89(3)degrees, V = 1332.4(3) Angstrom(3), Z = 4, D-c = 1.404 g cm(-3), mu(Mo Kalpha) = 0.28 mm(-1), and R = 0.036 for 2680 reflections [I > 2sigma(I)]. Molecule I is not planar, and the dihedral angle between the naphthaldeyde plane A [Cl-C11, 01] and the 4-chloroaniline plane B [C12-C17, C11, N1] is 20.1(3)degrees. An intramolecular hydrogen bond occurs between the hydroxyl oxygen and imine nitrogen atoms [2.528(3) Angstrom]. IR, H-1 NMR, and UV measurements and AM1 semiempirical quantum mechanical calculations support the keto form found in the X-ray structure.
• Antonov, Liudmil; Fabian, Walter M.F.; Nedeltcheva, Daniela, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 6, p. 1173 - 1179
  作者：Antonov, Liudmil、Fabian, Walter M.F.、Nedeltcheva, Daniela、Kamounah, Fadhil S.

  DOI：——

  日期：——