N,N-二-n-癸基苯胺 | 4960-25-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N-二-n-癸基苯胺
• 英文名称: N,N-didodecylaniline
• 英文别名: N,N-didodecylbenzamine
• CAS: 4960-25-2
• 化学式: C₃₀H₅₅N
• 分子量: 429.773
• InChiKey: XJEPUDKDCKLTSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  31
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二-n-癸基苯胺 在 sodium methylate 、 sodium carbonate 、 苦味酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 4-(4'-N,N-didodecylaminophenylazo)phenyl β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Amphiphilic Phenylazophenyl Glycosides and a Study of Their Liquid Crystal Properties

  摘要：

  Several 4-(4'-N,N-didodecylaminophenylazo)phenyl 1,2-trans glycosides 5a-e with various carbohydrate heads (beta-D-gluco, beta-D-galacto, beta-lacto, beta-D-xylo, and alpha-D-manno) have been synthesized. The key step was the formation of phenyldiazonium tetrafluoroborates 2a-e from the per-O-acetylated 4-aminophenyl glycosides 1a-e. These salts were condensed with N,N-didoclecylaniline under phase transfer conditions and the per-O-acetylated 4-(4'-N,N-didodecylaminophenylazo)phenyl 1,2-trans glycosides 4a-e were fully de-O-acetylated by the Zemplen method. The self-organizing liquid crystal properties of the compounds were investigated by a variety of techniques, including polarized light microscopy, differential scanning calorimetry, and X-ray diffraction. All but one of the materials exhibited smectic A, lamellar phases. Remarkably, the glucose derivative exhibited a rectangular disordered columnar phase. This result has implications with respect to the induced curvature created by the recognition processes of the glucose headgroup relative to the other sugar moieties and to the prevalence of various glycolipids in cell membranes.

  DOI：

  10.1021/ja037347x
• 作为产物：
  描述：

  十二烷醇 、 硝基苯 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 氢气 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以70%的产率得到N,N-二-n-癸基苯胺
  参考文献：
  名称：

  在无碱和无溶剂条件下，铱催化的胺和硝基苯与乙醇的醇烷基化反应生成叔胺

  摘要：

  在此，已经开发了一种用于选择性合成叔胺的有效且绿色的方法，该方法涉及用芳族或脂族醇进行的铱催化的各种伯胺的烷基化。值得注意的是，催化方案能够在不存在额外的碱和溶剂的情况下实现这种转化。此外，硝基苯与伯醇烷基化为叔胺也已通过相同的催化体系实现。进行了氘标记实验和一系列对照实验，结果表明在烷基化过程中可能存在分子间借氢途径。

  DOI：

  10.1021/acs.joc.8b03137

文献信息

• Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions
  作者：Qingzhu Zou、Chao Wang、Jen Smith、Dong Xue、Jianliang Xiao

  DOI：10.1002/chem.201501109

  日期：2015.6.26

  An efficient catalytic system for the alkylation of amines with either alcohols or amines under mild conditions has been developed, using cyclometallated iridium complexes as catalysts. The method has broad substrate scope, allowing for the synthesis of a diverse range of secondary and tertiary amines with good to excellent yields. By controlling the ratio of substrates, both mono‐ and bis‐alkylated

  使用环金属化铱配合物作为催化剂，已经开发出一种在温和条件下将胺与醇或胺烷基化的有效催化体系。该方法具有广泛的底物范围，允许以良好或优异的产率合成多种范围的仲胺和叔胺。通过控制底物的比例，可以高选择性获得单烷基化胺和双烷基化胺。特别是，甲醇可用作烷基化试剂，选择性地提供N-甲基化产物。对于该反应观察到强溶剂作用。
• π-Expanded α,β-Unsaturated Ketones: Synthesis, Optical Properties, and Two-Photon-Induced Polymerization
  作者：Rashid Nazir、Florent Bourquard、Evaldas Balčiūnas、Sabina Smoleń、David Gray、Nikolai V. Tkachenko、Maria Farsari、Daniel T. Gryko

  DOI：10.1002/cphc.201402646

  日期：2015.2.23

  the periphery of D‐π‐A‐π‐D molecules resulted in dyes with excellent solubility. These ketones absorb light in the region 400–550 nm. Many of them display strong solvatochromism so that the emission ranges from 530–580 nm in toluene to the near‐IR region in benzonitrile. Ketones based on cyclobutanone as central moieties display very high fluorescence quantum yields in nonpolar solvents, which decrease

  设计并合成了π膨胀的α，β-不饱和酮库。它们是通过维蒂希反应，Sonogashira反应和醛醇缩合反应的组合制备的。进一步证明，对于高度极化的苯乙烯和二苯乙炔衍生的醛，双醇醛缩合反应可以有效地进行。D外围的两个二烷基氨基的战略位置-π-A-π-D分子产生的染料具有极好的溶解性。这些酮吸收400-550 nm范围内的光。他们中的许多人表现出很强的溶剂致变色作用，因此甲苯的发射范围从530-580 nm到苄腈的近红外区。以环丁酮为中心部分的酮在非极性溶剂中显示出很高的荧光量子产率，在极性介质中急剧下降。这些新型功能性染料的光物理研究表明，与较简单的酮衍生物相比，它们具有增强的双光子吸收截面。由于所得染料的强极化作用，在800 nm处达到了200-300 GM的双光子吸收截面值，这要归功于酮基的存在，
• Posttreatment Technique for S_N2 Alkylation of Aromatics with Alkyl Halides: Aiming toward Large-Scale Synthesis of Building Blocks for Soft π-Molecular Materials
  作者：Ken Okamoto、Fengniu Lu、Takashi Nakanishi

  DOI：10.1246/bcsj.20180075

  日期：2018.8.15

  byproduct olefin contaminants in products of SN2 alkylation reactions of aromatic compounds can be efficiently removed by sequential posttreatments with a base and a boron compound (sodium borohydride or 9-borabicyclo[3.3.1]nonane), followed by column chromatography on silica gel. These treatments permit large-scale purification of various alkylated aromatics, thereby assisting in the development of soft

  通过用碱和硼化合物（硼氢化钠或 9-硼双环 [3.3.1] 壬烷）顺序后处理，可以有效去除芳族化合物 SN2 烷基化反应产物中未反应的卤代烷和副产物烯烃污染物，然后在硅胶。这些处理允许大规模纯化各种烷基化芳烃，从而有助于开发软 π 共轭材料，例如用于半导体聚合物的单体或烷基化 π 功能液体。
• Cruciform 9,10-distyryl-2,6-bis(p-dialkylamino-styryl)anthracene homologues exhibiting alkyl length-tunable piezochromic luminescence and heat-recovery temperature of ground states
  作者：M. Zheng、D. T. Zhang、M. X. Sun、Y. P. Li、T. L. Liu、S. F. Xue、W. J. Yang

  DOI：10.1039/c3tc32035a

  日期：——

  A series of 2,6-bis(p-dialkylaminostyryl)-9,10-distyrylanthracene (FCn) cruciforms with N-alkyl chains of different lengths have been synthesized, and their aggregation-enhanced fluorescence and piezochromic luminescence (PFC) behaviours are investigated. These 9,10-distyrylanthracene-containing cruciforms exhibit relatively low fluorescence quantum yields (Φ) in THF solution (Φ ≈ 10%) and moderate aggregation-enhanced emission in aqueous media (Φ ≈ 25%), but strong and chain length-dependent solid-state fluorescence emission. Grinding and pressing experiments indicate that they are all effective PFC materials in terms of mechanical stress-induced spectral shifts (ΔλPFC = 23–54 nm), moreover, the longer alkyl-containing FCn shows a larger ΔλPFC. Powder X-ray diffraction and differential scanning calorimetry measurements reveal that the transformation between the crystalline and amorphous states upon external stimuli is responsible for the reversible PFC behaviour. It is found that increasing the N-alkyl length could effectively decrease the cold-crystallization temperature of the ground states to render the PFC states with a tunable heat-recovering temperature, and ground FC10 and FC12 solids can recover spontaneously to their original states at room temperature.

  合成了一系列具有不同长度N-烷基链的2,6-bis(p-二烷基氨基苯乙烯)-9,10-二苯乙烯蒽（FCn）十字形化合物，并研究了它们的聚集增强荧光和压电变色发光（PFC）特性。这些含有9,10-二苯乙烯蒽的十字形化合物在THF溶液中的荧光量子收益（Φ）相对较低（Φ ≈ 10%），但在水相介质中表现出适度的聚集增强发光（Φ ≈ 25%），但在固态中呈现出强烈且依赖链长的荧光发射。研磨和压制实验表明，这些材料在机械应力诱导下的光谱位移（ΔλPFC = 23–54 nm）都表现出有效的PFC特性，此外，较长的烷基链FCn显示出更大的ΔλPFC。粉末X射线衍射和差示扫描量热法测量表明，外部刺激下晶态和非晶态之间的转变是可逆PFC行为的原因。研究发现，增加N-烷基链的长度可以有效降低基态的冷结晶温度，从而使PFC状态的热恢复温度可调，且基态FC10和FC12固体可以在室温下自发恢复到其原始状态。
• Quadrupolar Benzobisthiazole-Cored Arylamines as Highly Efficient Two-Photon Absorbing Fluorophores
  作者：Peter Hrobárik、Veronika Hrobáriková、Vladislav Semak、Peter Kasák、Erik Rakovský、Ioannis Polyzos、Mihalis Fakis、Peter Persephonis

  DOI：10.1021/ol503137p

  日期：2014.12.19

  benzobisthiazole moieties as the electron-accepting core has revealed the linear centrosymmetric benzo[1,2-d:4,5-d′]bisthiazole as the most promising building block for engineering chromophores displaying high two-photon absorption (TPA) in the near-IR region, as also confirmed experimentally. The ease of synthesis of quadrupolar derivatives thereof, combined with extraordinarly high TPA action cross sections

  包含五个异构体苯并双噻唑部分作为电子接受核的新型D-π-A-π-D苯乙烯胺的计算机辅助设计表明，线性中心对称的苯并[1,2- d：4,5- d ']双噻唑为工程生色团的最有希望的构建基块，在近红外区域显示出高的双光子吸收（TPA），这也得到了实验的证实。便于其四极衍生物的合成的，具有高extraordinarly TPA动作的横截面结合（δ TPA Φ ˚F > 1500 GM），使得这些杂芳族体系，如3D荧光成像的诊断剂特别有吸引力的。