(Z)-1-((phenylamino)methylene)naphthalen-2-one | 55135-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-((phenylamino)methylene)naphthalen-2-one
• 英文别名: 1-Anilinomethylen-2-oxo-1,2-dihydro-naphthalin；N-Phenyl-2-oxo-1.2-dihydro-naphthyliden-(1)-methylamin；(1Z)-1-(anilinomethylidene)naphthalen-2-one
• CAS: 55135-70-1
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: CWCYUNGEXLJKIK-VBKFSLOCSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  458.2±45.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  19.0
• 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

• 作为反应物：
  描述：

  (Z)-1-((phenylamino)methylene)naphthalen-2-one 以 氘代氯仿 为溶剂， 生成 (E)-1-((phenylimino)methyl)naphthalen-2-ol
  参考文献：
  名称：

  Alarcon, Sergio H.; Olivieri, Alejandro C.; Gonzales-Sierra, Manuel, Journal of the Chemical Society. Perkin transactions II, 1994, # 5, p. 1067 - 1070

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-((phenylimino)methyl)naphthalen-2-ol 以 四氯化碳 为溶剂， 生成 (Z)-1-((phenylamino)methylene)naphthalen-2-one
  参考文献：
  名称：

  取代基和溶剂对苯胺和萘酚偶氮衍生物质子转移平衡的影响。多核核磁共振研究和理论计算

  摘要：

  摘要 在一系列 2-羟基萘-1-甲醛和 2-萘酚的偶氮衍生物中比较了由质子转移引起的互变异构平衡。尽管结构相似，但这些系统对溶液状态的质子转移特性具有不同的取代基影响。比较研究是在各种溶剂中使用 1 H、 13 C 和 15 N NMR 光谱进行的。Hartree-Fock ab initio 计算涉及互变异构体的相对稳定性和基态的完整几何优化，与实验观察结果一致。

  DOI：

  10.1016/s0022-2860(03)00208-4

文献信息

• Spectral kinetic characteristics of the photoisomerization products of naphthylmethylideneiminospironaphthopyran induced by photolysis at different wavelengths
  作者：P. P. Levin、N. L. Zaichenko、A. I. Shienok、L. S. Kol’tsova、I. R. Mardaleishvili、A. S. Tatikolov

  DOI：10.1007/s11172-012-0078-6

  日期：2012.3

  The spectral kinetic characteristics of intermediates generated by photolysis with light at the wavelengths 337 and 430 or 470 nm of the photobifunctional compound (PBC), 1,3-dihydro-5-(2-hydroxy-1-naphthylmethylideneimino)-1,3,3-trimethylspiro[2H-indole-2,3-[3H]-naphtho[2,1-b]pyran], whose molecule combines the spironaphthopyran and hydroxyazomethine fragments, and also parameters of model compounds, viz., naphthylmethylideneimine and spironaphthopyran, were studied in methanol and toluene. The relative quantum yields of formation of different intermediates of PBC were measured relatively to model compounds, namely, trans-keto isomer formed due to cis-trans-isomerization and prototropic equiliration in the azomethine fragment, and in the merocyanine form generated by spiro bond opening. It was found that the photolysis of the PBC with light at the wavelengths λ = 430 or 470 nm nearly no produces the merocyanine form, whereas the relative yield of the trans-keto tautomer is ∼0.6. For PBC photolysis at λ = 337 nm, the yield of the merocyanine form is ∼0.2 and the yield of the trans-keto isomer decreases substantially (≤0.2). The solvent nature affects the kinetic behavior of the system. The consistency of the isomerization and proton transfer processes is discussed.

  在波长为 337 和 430 或 470 纳米的光下光解 1,3-二氢-5-(2-羟基-1-萘亚甲基亚氨基)-1,3,3-三甲基螺[2H-吲哚-2,3-[3H]-萘并[2,1-b]吡喃]光功能化合物 (PBC)所产生的中间产物的光谱动力学特性、1,3-二氢-5-(2-羟基-1-萘亚甲基亚氨基)-1,3,3-三甲基螺[2H-吲哚-2,3-[3H]-萘并[2,1-b]吡喃]，其分子结合了螺萘并吡喃和羟基氮甲基片段。,在甲醇和甲苯中研究了萘亚甲基亚胺和螺萘并吡喃的参数。相对于模型化合物，测量了形成 PBC 不同中间体的相对量子产率，即偶氮亚甲基片段中顺反异构和原向平衡形成的反式酮异构体，以及螺键打开产生的美蓝形式。研究发现，波长为 λ = 430 或 470 纳米的光对 PBC 进行光解时，几乎不产生美花氨酸形式，而反式酮同系物的相对产率为 0.6。在 λ = 337 纳米波长下进行 PBC 光解时，美拉德菁形式的产率为∼0.2，反式酮异构体的产率大幅下降（≤0.2）。溶剂性质会影响体系的动力学行为。讨论了异构化和质子转移过程的一致性。
• 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：——
• Factors determining tautomeric equilibria in Schiff bases
  作者：Martha Flores-Leonar、Nuria Esturau-Escofet、José M. Méndez-Stivalet、Armando Marı´n-Becerra、Carlos Amador-Bedolla

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  日期：2011.12

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