N-(2-hydroxy-1-naphthylmethylene)methylamine | 880-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-hydroxy-1-naphthylmethylene)methylamine
• 英文别名: 1-(methyliminomethyl)naphthalen-2-ol；1-(N-methyl-iminomethyl)-2-naphthol；Naphmet；1--2-naphthol；2-Hydroxy-naphthaldehyd-methylimin；2-Naphthalenol, 1-[(methylimino)methyl]-
• CAS: 880-99-9
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: YLXTWYXVORBYHH-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C(Solv: hexane (110-54-3))
• 沸点：
  350.6±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  N-(2-hydroxy-1-naphthylmethylene)methylamine 、 二氯二氧化钼 以 乙醚 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  Molecular and Intracomplex Dioxomolybdenum(VI) Compounds with Substituted R1-Salycilidene-N-methylimines (HL): Crystal Structure of Three [MoO2(L)2] Complexes (R1 = H, 5-Br, 5-Cl)

  摘要：

  The synthesis and IR spectroscopic and X-ray diffraction studies of three [MoO2(L-n)(2)] complexes with n = 1 (R = H, repeatedly) (I), n = 4 (R = Br) (II), and n = 3 (R = Cl) (III) have been performed. The molybdenum atoms in the structures of complexes I-III have a typical octahedral coordination with dioxo ligands in cis-positions, atoms N(L-n) in trans-positions to O(oxo), and atoms O(L-n) in cis-positions to oxo ligands. Ligands L-n are bidentate chelate (N, O).

  DOI：

  10.1134/s003602361808020x
• 作为产物：
  描述：

  甲胺 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 生成 N-(2-hydroxy-1-naphthylmethylene)methylamine
  参考文献：
  名称：

  N-(邻羟基萘亚甲基)甲胺及其互变异构体的稳定性

  摘要：

  摘要 利用温度核磁共振数据和氘同位素对它们在CDCl 3 、CD 3 CN和DMSO中的13 C化学位移的影响，确定了三种异构体N -(邻-羟基萘亚甲基)甲胺质子转移平衡的热力学参数。 - d 6。已经执行了真空和溶液中 OH 和 NH 互变异构体的 DFT 几何优化以及能量、偶极矩和 HOMA（芳香性）参数的计算。所研究的三种异构体的平衡常数差异的起源解释是基于准环中涉及分子内氢键的 π 电子离域竞争的差异、极性和周围相互作用的差异。

  DOI：

  10.1016/j.molstruc.2010.06.024

文献信息

• Luminescent property and catalytic activity of Ru(II) carbonyl complexes containing N, O donor of 2-hydroxy-1-naphthylideneimines
  作者：M. Sivagamasundari、R. Ramesh

  DOI：10.1016/j.saa.2006.07.010

  日期：2007.5

  (where E=P; B=PPh(3), py or pip: E=As; B=AsPh(3)) in benzene afforded new stable ruthenium(II) carbonyl complexes of the general formula [Ru(Cl)(CO)(EPh(3))(B)(L)] (L=anion of bidentate Schiff bases). The structure of the new complexes was investigated using elemental analyses, spectral (FT-IR, UV-vis and (1)H NMR) and electrochemical studies and is found to be octahedral. All the metal complexes exhibit

  螯合配体（通过2-羟基-1-萘醛与各种伯胺的缩合获得）与[RuHCl（CO）（EPh（3））（2）（B）]（其中E = P； B = PPh（3），py或pip：苯中的E = As; B = AsPh（3））得到通式[Ru（Cl）（CO）（EPh（3））的新的稳定的钌（II）羰基络合物（B）（L）]（L ＝双齿席夫碱的阴离子）。使用元素分析，光谱（FT-IR，UV-vis和（1）H NMR）和电化学研究对新配合物的结构进行了研究，结果发现它们是八面体的。所有的金属络合物在可见光区域均表现出特征性的MLCT吸收和发光带。基于金属离子周围的配体环境解释了钌（II）配合物的发光效率。在N-甲基吗啉-N-氧化物（NMO）作为氧源的情况下，这些络合物催化伯醇和仲醇氧化为相应的羰基化合物。提出了形成高价Ru（IV）= O物种作为催化中间体的方法。
• Control of Stereochemistry at the Metal Center in Planar-Chiral Cyclopentadienyl Ruthenium Complexes with Anchor Phosphine on Complexation with Salicylideneaminato Ligands
  作者：Kiyotaka Onitsuka、Yoshiki Ajioka、Yuji Matsushima、Shigetoshi Takahashi

  DOI：10.1021/om0102246

  日期：2001.7.1

  studies including NOE measurements revealed that the configuration of the major isomers is SCpRRu/RCpSRu. Similar reactions of planar-chiral cyclopentadienyl ruthenium complexes [η5-C5H2(Me)(R)COOEt}Ru(PPh3)(MeCN)2][PF6] (7) (7a, R = Me; 7b, R = Ph) having no anchor phosphine ligands with 2 also gave salicylideneaminato complexes (8 and 9) with a low selectivity. Epimerization of a pure sample of the major

  平面手性的环戊二烯基膦钌配合物的反应[η 5，η 1 - C 5 ħ 2（Me）的（R）COO（CH 2）2 PPH 2 }钌（MeCN中）2 ] [PF 6 ]（1A， R = Me; 1b，R = Ph）与水杨内酰胺钠（2）导致形成水杨内酰胺络合物（3和4，R = Me; 5和6，R = Ph）以高选择性（高达> 99％de）诱导金属中心手性。产物的非对映选择性不取决于水杨基亚胺基配体的芳环上的取代基，而是取决于环戊二烯基和亚氨基上的氮的取代基。X射线衍射和NMR研究（包括NOE测量）表明，主要异构体的构型为S Cp R Ru / R Cp S Ru。平面手性的环戊二烯基的钌络合物的类似反应[η 5 - C 5 ħ 2（Me）的（R）COOEt烷基}钌（PPH 3）（MeCN中）2 ] [PF 6 ]（7）（7a，R ＝ Me；7b，R ＝ Ph）不具有2的锚定膦配体，也产生了低选
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: U: SVol.E2, 1.7.5, page 60 - 104
  作者：

  DOI：——

  日期：——
• Structures and properties of di-μ-oxo dimanganese(IV) complexes with bidentate Schiff bases, N-alkyl-substituted-salicylideneamine
  作者：Hitoshi Torayama、Hideyuki Asada、Manabu Fujiwara、Takayuki Matsushita

  DOI：10.1016/s0277-5387(98)00144-2

  日期：1998.11

  Novel di-mu-oxo dimanganese(IV) complexes, [Mn-IV(N-R-X-sal)(2)(mu-O)](2), with bidentate Schiff base ligands, N-alkyl-substituted-salicylideneamine, N-R-X-salH [R= CH3(Me), C2H5 (Et), n-C3H, (Pr), n-C4H9 (Bu), n-C6H13 (Hx), n-C8H17 (Oct), II-C10H21 (Dec), n-C12H25 (Dod), or n-C18H37 (Octd) and X = H or 5,6-benzo]: have been prepared by their reaction with potassium permanganate (KMnO4) in MeCN, while stirring at room temperature. These complexes were characterized by spectroscopy, magnetic susceptibility, thermal analysis and X-ray crystallography. The structures consist of a Mn-2(IV)(mu-O)(2) core with a Mn-Mn separation of 2.731 (4) Angstrom for [Mn-IV(N-Me-sal)(2)(mu-O)](2), 1, 2.769(2) Angstrom for [Mn-2(IV)(N-Et-sal)(2)(mu-O)](2), 2, 2.780(2) Angstrom for [(Mn-IV-Hx-sal)(2)(mu-O)](2), 5, 2.780(2)Angstrom for [Mn-IV(N-Dec-sal)(2)(mu-O)](2), 7, and 2.756(3) Angstrom for [Mn-IV(N-Me-5,6-benzo-sal)(2)(mu-O)](2), 10. The complex 1 is the first di-mu-oxo dimanganese(IV) complex having asymmetrical form in which two manganese ions adopt different configurations each other. Moreover, the complexes 5 and 7 are found to exhibit the longest one among all of the Mn-Mn separation observed for the structurally characterized Mn-2(mu-O)(2) complexes prior to this work. The antiferromagnetic exchange interaction has been found to be J= -83 and -188 cm(-1) for 1 and 7, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Benzenoid-quinoid tautomerism of azomethines and their structrual analogues XXX. Molecular structure of gallium and boron organometalic compounds with tautomeric azomethines
  作者：V.I. Bregadze、N.G. Furmanova、L.M. Golubinskaya、O.Y. Kompan、Y.T. Struchkov、V.A. Bren、Zh.V. Bren、A.E. Lyubarskaya、V.I. Minkin、L.M. Sitkina

  DOI：10.1016/s0022-328x(00)93325-4

  日期：1980.6