2-((hexadecylimino)methyl)phenol | 16308-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-((hexadecylimino)methyl)phenol
• 英文别名: N-hexadecylsalicylaldimine；salicylidene-n-hexadecylamine；N-hexadecylsalicylideneimine；N-hexadecylsalicylideneamine；2-(hexadecyliminomethyl)phenol
• CAS: 16308-55-7
• 化学式: C₂₃H₃₉NO
• 分子量: 345.569
• InChiKey: IRXQUNJPJQPYNP-UHFFFAOYSA-N

物化性质

• 熔点：
  36 °C
• 沸点：
  461.6±28.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-((hexadecylimino)methyl)phenol 生成 6-[1-Hexadecylamino-meth-(Z)-ylidene]-cyclohexa-2,4-dienone
  参考文献：
  名称：

  Zhao, Jianzhang; Zhao, Bing; Xua, Weiqing, Journal of Chemical Research - Part S, 2003, # 5, p. 292 - 293

  摘要：

  DOI：
• 作为产物：
  描述：

  6-[1-Hexadecylamino-meth-(Z)-ylidene]-cyclohexa-2,4-dienone 生成 2-((hexadecylimino)methyl)phenol
  参考文献：
  名称：

  Zhao, Jianzhang; Zhao, Bing; Xua, Weiqing, Journal of Chemical Research - Part S, 2003, # 5, p. 292 - 293

  摘要：

  DOI：

文献信息

• Anti-mycobacterial activities of copper(II) salicylaldimine complexes derived from long-chain aliphatic amines
  作者：Alyssa E. Patterson、Eric G. Bowes、Allyson Bos、Taryn O’Neill、Haoxin Li、Andrew Flewelling、Christopher M. Vogels、Andreas Decken、Christopher A. Gray、Stephen A. Westcott

  DOI：10.1139/cjc-2013-0274

  日期：2013.11

  Twelve copper(II) Schiff base complexes derived from lipophilic amines have been prepared using either salicylaldehyde or ortho-vanillin via a microwave-assisted reaction. All complexes have been obtained elementally pure and an X-ray diffraction of an isopentyl derivative has confirmed the structure of these compounds. All complexes showed a promising degree of anti-mycobacterial activity against

  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。
• Helicity Control of Supramolecular Gel Fibers Consisting of an Achiral Ni^IIComplex in a Chiral Nematic Solvent
  作者：Takatoshi Maeda、Yuuki Kuwajima、Takuya Akita、Yosuke Iwai、Naruyoshi Komiya、Yoshiaki Uchida、Takeshi Naota

  DOI：10.1002/chem.201801992

  日期：2018.8.27

  supramolecular chirality of aggregates consisting of achiral trans‐bis(salicylaldiminato)NiII complex 1 bearing long alkyl chains can be generated and controlled precisely in a chiral nematic liquid‐crystalline (LC) solvent, whereas the complex naturally forms achiral gel fibers in achiral nematic LC solvents and crystals in nonmesogenic solvents. The direction and intensity of the helicity of the gel fibers

  可以在手性向列液晶（LC）溶剂中精确生成并控制由带有长烷基链的非手性反式-双-（salicylaldiminato）Ni II复合物1形成的聚集体的超分子手性，而该复合物在非手性中自然形成非手性凝胶纤维向列型LC溶剂和非介晶溶剂中的晶体。凝胶纤维的螺旋度的方向和强度为1可以通过螺旋扭曲的性质和手性掺杂剂的浓度来调节处于LC凝胶状态的C -1。在LC凝胶的圆二色性（CD）光谱中以及通过直接SEM观察干燥的凝胶纤维，可以精确检测出螺旋度控制。XRD分析表明，该复合物基于人字形的层状排列的灵活性是凝胶纤维的LC特异性凝胶化和螺旋度控制的关键。
• Solid-State Phosphorescence of<i>trans</i>-Bis(salicylaldiminato)platinum(II) Complexes Bearing Long Alkyl Chains: Morphology Control towards Intense Emission
  作者：Naruyoshi Komiya、Nao Itami、Takeshi Naota

  DOI：10.1002/chem.201301087

  日期：2013.7.15

  Morphology control for intense solid‐state phosphorescence of non‐emissive, but potentially emissive crystals of platinum complexes and the mechanistic rationale are described. A series of trans‐bis(salicylaldiminato)platinum(II) complexes bearing linear alkyl chains (1 a: n=5; 1 b: n=8; 1 c: n=12; 1 d: n=14; 1 e: n=16; 1 f: n=18) was synthesized and the solid‐state emission properties were examined

  描述了用于非发射性但潜在发射性的铂配合物晶体的强烈固态磷光的形态学控制及其机理。一系列带有线性烷基链的反式-双（水杨基铝二氨基）铂（II）配合物（1 a：n = 5; 1 b：n = 8; 1 c：n = 12; 1 d：n = 14; 1 e：合成了n = 16; 1 f：n = 18），并使用在各种沉淀条件下制备的晶体/聚集体检查了固态发射特性。1 e的晶体使用“动力学”条件，包括快速冷却，高浓度，溶剂和不良溶剂来制备，发出强烈的黄色磷光（λ最大UV照射下= 545纳米）在298K为0.36绝对量子效率，而所有的晶体1点中的-图1f使用“热力学”条件，包括缓慢冷却，低浓度制备，并且良溶剂要么非或更少发射与Φ 298K 0.12（值1），0.11（图1b），0.10（1c中），0.07在相同的测量条件下（1 d），0.02（1 e）和0.02（1 f）。无定形固体图1e，通过快速冷却和冷冻干燥制备的，也非发射（Φ
• Coordination Amphiphile: Design of Planar-Coordinated Platinum Complexes for Monolayer Formation at an Air-Water Interface Based on Ligand Characteristics and Molecular Topology
  作者：Junya Adachi、Masaya Naito、Sho Sugiura、Ngoc Ha-Thu Le、Shoma Nishimura、Shufang Huang、Shuichi Suzuki、Soichiro Kawamorita、Naruyoshi Komiya、Jonathan P. Hill、Katsuhiko Ariga、Takeshi Naota、Taizo Mori

  DOI：10.1246/bcsj.20220086

  日期：2022.6.15

  hydrophilicity of SA can assist in the formation of a stable monolayer if hydrophobic and hydrophilic chains are introduced to the structure. In contrast, IA complexes exhibit topological specificity; imidazolato and pyrazolato complexes form monolayers only for non-vaulted and vaulted complex, respectively. Molecular modelling and association constants of the compounds suggest that an appropriate hydrophilicity

  我们的目标是在“配位两亲物”概念中确定分子设计对于在空气-水界面形成单分子层的重要性，该概念基于配体特征和分子拓扑结构。为此，已经制备了五种含有配位平面的铂配合物，包括水杨醛亚胺（SA）和β-（亚氨基甲基）偶氮（IA）配合物，其中配体特性受到控制。然后检查聚亚甲基拱形和非拱形复合物以评估分子拓扑结构对界面活性的影响。SA配合物倾向于在空气-水界面发生随机聚集，而SA的弱亲水性如果将疏水和亲水链引入结构中，则可以帮助形成稳定的单分子层。相比之下，IA配合物表现出拓扑特异性。咪唑啉和吡唑啉配合物分别仅对非拱形和拱形配合物形成单分子层。化合物的分子模型和缔合常数表明配位平面的适当亲水性和涉及氢键的分子间相互作用是单层形成的重要因素。
• 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.