1-hydroxy-2-octyliminomethylbenzene | 16308-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-hydroxy-2-octyliminomethylbenzene
• 英文别名: 2-[(octylimino)methyl]-phenol；N-salicylidene-octylamine；N-n-octyl-salicylideneamine；2-(Octylimino-methyl)-phenol；N-n-octyl-salicylaldimin；N-Octylsalicylidenamin；Salicyliden octylamine；2-(octyliminomethyl)phenol
• CAS: 16308-58-0
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: IUZQHWHGHIRMGG-UHFFFAOYSA-N

物化性质

• 沸点：
  349.4±25.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-hydroxy-2-octyliminomethylbenzene 、 copper(II) sulfate 生成 bis(N-octylsalicylideniminato-N,O)copper(II)
  参考文献：
  名称：

  来自长链脂肪胺的铜 (II) 水杨醛亚胺配合物的抗分枝杆菌活性

  摘要：

  已经使用水杨醛或邻香兰素通过微波辅助反应制备了十二种衍生自亲脂胺的铜 (II) 席夫碱配合物。所有配合物均已获得元素纯，异戊基衍生物的 X 射线衍射证实了这些化合物的结构。所有复合物都显示出对结核分枝杆菌的有希望的抗分枝杆菌活性，其中活性似乎随着脂肪链长度的增加而增加。

  DOI：

  10.1139/cjc-2013-0274
• 作为产物：
  描述：

  辛胺 、 水杨醛 在 甲醇 作用下， 生成 1-hydroxy-2-octyliminomethylbenzene
  参考文献：
  名称：

  Copper (II) and Nickel (II) N-(n-alkyl)salicylaldimine Chelates

  摘要：

  DOI：

  10.1021/jo01357a025

文献信息

• Synthesis and characterization of bis[salicylideneaminato] palladium(II) complexes. Molecular structure of bis[N-(n-butyl)(3-benzyloxy)-2-salicylideneaminato]-palladium(II), pd(C18H20NO2)2]
  作者：Mauro Ghedini、Concettina Pellegrino、Salvatore Armentano、Giovanni De Munno、Giuseppe Bruno

  DOI：10.1016/s0020-1693(00)81638-2

  日期：1986.12

  materials for practical applications. Attempting to correlate mesomorphic properties with molecular structure and crystal packing mode, we have investigated some complexes obtained from Schiff bases of long chain aliphatic amines and salicylaldehyde or 2,3-dihydroxybenzaldehyde derivatives. The X-ray structural analysis of bis[N-(n-butyl)(3-benzyloxy)-2-salicylideneaminato] palladium [II] is also reported.

  具有液晶性质的过渡金属化合物可以是实际应用中令人感兴趣的材料。为了使介晶性质与分子结构和晶体堆积模式相关联，我们研究了一些从长链脂族胺和水杨醛或2,3-二羟基苯甲醛衍生物的席夫碱获得的配合物。还报道了双[ N-（正丁基）（3-苄氧基）-2-水杨酰亚氨合]钯[II]的X射线结构分析。
• Synthesis, characterization and anticancer properties of (salicylaldiminato)platinum(II) complexes
  作者：Alyssa E. Patterson、Jessica J. Miller、Brittany A. Miles、Erin L. Stewart、Josée-Marie E.J. Melanson、Christopher M. Vogels、Amanda M. Cockshutt、Andreas Decken、Pier Morin、Stephen A. Westcott

  DOI：10.1016/j.ica.2014.02.028

  日期：2014.5

  Twelve new (salicylaldiminato) platinum(II) complexes have been prepared, characterized and examined for their in vitro cytotoxic properties against three human glioma cell lines LN18, LN405 and Hs683. Initial biotesting was done on platinum complexes 1-6, which display a wide range of physicochemical properties. Whereas introduction of aromatic rings in the complexes did not seem to have a significant impact on bioactivities, the length of the aliphatic group positively correlated with cytotoxicity in all cell lines. Complexes 2 and 3 were found to be particularly potent against LN18 cells as demonstrated by stronger cell growth inhibition when compared to cisplatin. These initial findings led us to develop an additional series of mono (salicylaldiminato) platinum(II) complexes 7-12, which were subjected to additional cytotoxicity studies but were less cytotoxic compared to the bis Schiff base complexes. These organometallic compounds could serve as interesting starting points for the development of novel therapeutic strategies to treat brain tumors. (C) 2014 Elsevier B.V. All rights reserved.
• 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.
• Effects of chloride ions on electrochemical reactions of manganese(III) complexes
  作者：Megumi Kasuno、Masaki Hayano、Manabu Fujiwara、Takayuki Matsushita

  DOI：10.1016/j.poly.2008.10.073

  日期：2009.2

  Electrochemical reactions of manganese(III) complexes, Mn-III(L)X (L; salen, salpn, 5-NO2-salen or 5-NO2-salpn, X; Cl, Br or NO2) and Mn-III(L')(2)X (L': N-Bu-sal, N-Oct-sal, N-Oct-5-Br-sal or N-Oct-5-NO2-sal, X; Cl or Br), were investigated by voltammetry at a glassy carbon electrode in the absence/presence of Cl- in acetonitrile solution. By the addition of Cl-, oxidation processes of Mn-III(L)X and Mn-III(L')(2)X have been found to be improved from quasi-reversible to reversible, and their oxidation products, [Mn-IV(L)X](+) and [Mn-IV(L')(2)X](+), were stabilized by the combination with Cl- resulting in [Mn-IV(L)Cl-2] and [Mn-IV(L')(2)Cl-2], respectively. On the other hand, the reduction processes of Mn-III(L)X and Mn-III(L')(2)Cl were not so significantly affected by Cl- as those observed for their oxidation. Other types of manganese(III) complexes and iron(III) complex were also investigated. The present Study may clarify the role of Cl- being involved in OEC (oxygen-evolving center) in photosystem II. (C) 2008 Elsevier Ltd. All rights reserved.
• Metal complexes of π-expanded ligands (2): Synthesis and characterizations of bis[2-[(octylimino)methyl]-1-pyrenolato-N,O] palladium(II) and the stabilized vacant <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.gif" overflow="scroll"><mml:mrow><mml:msub><mml:mrow><mml:mi>d</mml:mi></mml:mrow><mml:mrow><mml:msup><mml:mrow><mml:mi>x</mml:mi></mml:mrow><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:msup><mml:mo>-</mml:mo><mml:msup><mml:mrow><mml:mi>y</mml:mi></mml:mrow><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:msup></mml:mrow></mml:msub></mml:mrow></mml:math> orbital
  作者：Luong Xuan Dien、Ken-ichi Yamashita、Ken-ichi Sugiura

  DOI：10.1016/j.poly.2015.07.043

  日期：2015.12

  A palladium(II) complex of our pi-expanded ligand, i.e., a salicylaldimine-style ligand based on pyrene, was synthesized and characterized. A treatment of this ligand (L) with palladium(II) acetate afforded the desired metal complex, Pd(II)L-2, 3(Pd). Single crystal diffraction study revealed that this complex is a square planar four-coordinate palladium(II) complex. The structure of 3(Pd), i.e., shapes of the complexes, bond distances and angles, packing motif, is nearly identical with those of the previously reported the platinum(II) complexes, 2(Pt), as well as in the range of the values reported for structurally similar salicylaldiminato palladium(II) complexes. Although the IR spectrum of 3(Pd) is similar to that of 2(Pt), H-1 NMR of 3(Pd) reflects the electronegative character of palladium, i.e., higher field shift was observed comparing with the spectrum of 2(Pt). The incorporated palladium induces the stabilization of the Kohn-Sham orbitals containing d-orbital coefficients of the metal. The significant difference is the following: the LUMO of 2(Pt) is the pi-orbitals of the ligand, contrary, that of 3(Pd) is the vacant 4d(x2-y2) of Pd. Therefore, excitations from occupied pi-orbitals to this LUMO are mostly forbidden and the allowed transition to LUMO+1 and the higher pi-orbitals were shifted to blue region. The lowest excitation energy of 3(Pd) was found at 497 nm. (C) 2015 Elsevier Ltd. All rights reserved.