N-癸基苯胺 | 3007-73-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-癸基苯胺
• 英文名称: N-decylaniline
• CAS: 3007-73-6
• 化学式: C₁₆H₂₇N
• 分子量: 233.397
• InChiKey: VTHOTOFWYDBNID-UHFFFAOYSA-N

物化性质

• 沸点：
  150-152 °C(Press: 1 Torr)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-癸基苯胺 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 sodium 4,4'-(12,21-dioxo-11,13,20,22-tetraazadotriacontane-11,22-diyl)dibenzenesulfonate
  参考文献：
  名称：

  Synthesis of Three Novel Anionic Gemini Surfactants and Comparative Studies of Their Assemble Behavior in the Presence of Bovine Serum Albumin

  摘要：

  Three novel anionic sulfonate gemini surfactants, sodium 4,4'-(10,19-dioxo-9,11,18,20-tetraazaoctacosane-9,20-diyl) dibenzenesulfonate (Surfactant I), sodium 4,4'-(12,21-dioxo-11,13,20,22-tetraazadotriacontane-11,22-diyl) dibenzenesulfonate (Surfactant II), and sodium 4,4'-(14,23-dioxo-13,15,22,24-tetraazahezatriacontane-13,24-diyl) dibenzenesulfonate (Surfactant III), with different lengths of hydrophobic tail have been synthesized, and their assembly behavior in the presence of bovine serum albumin (BSA) has been studied using spectral methods and molecular modeling methods at physiological pH and 298 K Critical micelle concentrations (CMCs) of the three surfactants have been determined by surface tension measurements. Despite the obvious decrease of CMC with the increase of tail length, fluorescence spectra have shown much closer CAC in the presence of BSA. Surfactant II shows the highest CAC of 3.19 X 10(-5) mol L-1 compared with the other two. The polarity of the microenvironment in BSA surfactant systems has been investigated using pyrene as the probe. In addition, far-UV CD spectra studied the change of the secondary structure content of BSA caused by the three surfactants. The features of the assembly behavior were discussed by three concentration regions. Surfactant II could unfold the protein much more efficiently than the other two surfactants at low concentration, but at high concentration, the change of the secondary structure and the formation of hydrophobic microenvironment show a direct relationship to the length of the hydrophobic tail with the increase of the surfactant concentration.

  DOI：

  10.1021/la204212s
• 作为产物：
  描述：

  N-苯基癸酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-癸基苯胺
  参考文献：
  名称：

  Synthesis of Three Novel Anionic Gemini Surfactants and Comparative Studies of Their Assemble Behavior in the Presence of Bovine Serum Albumin

  摘要：

  Three novel anionic sulfonate gemini surfactants, sodium 4,4'-(10,19-dioxo-9,11,18,20-tetraazaoctacosane-9,20-diyl) dibenzenesulfonate (Surfactant I), sodium 4,4'-(12,21-dioxo-11,13,20,22-tetraazadotriacontane-11,22-diyl) dibenzenesulfonate (Surfactant II), and sodium 4,4'-(14,23-dioxo-13,15,22,24-tetraazahezatriacontane-13,24-diyl) dibenzenesulfonate (Surfactant III), with different lengths of hydrophobic tail have been synthesized, and their assembly behavior in the presence of bovine serum albumin (BSA) has been studied using spectral methods and molecular modeling methods at physiological pH and 298 K Critical micelle concentrations (CMCs) of the three surfactants have been determined by surface tension measurements. Despite the obvious decrease of CMC with the increase of tail length, fluorescence spectra have shown much closer CAC in the presence of BSA. Surfactant II shows the highest CAC of 3.19 X 10(-5) mol L-1 compared with the other two. The polarity of the microenvironment in BSA surfactant systems has been investigated using pyrene as the probe. In addition, far-UV CD spectra studied the change of the secondary structure content of BSA caused by the three surfactants. The features of the assembly behavior were discussed by three concentration regions. Surfactant II could unfold the protein much more efficiently than the other two surfactants at low concentration, but at high concentration, the change of the secondary structure and the formation of hydrophobic microenvironment show a direct relationship to the length of the hydrophobic tail with the increase of the surfactant concentration.

  DOI：

  10.1021/la204212s

文献信息

• Organic Ligand-Free Alkylation of Amines, Carboxamides, Sulfonamides, and Ketones by Using Alcohols Catalyzed by Heterogeneous Ag/Mo Oxides
  作者：Xinjiang Cui、Yan Zhang、Feng Shi、Youquan Deng

  DOI：10.1002/chem.201001915

  日期：2011.1.17

  that is, amines, carboxamides, sulfonamides, and ketones, were successfully synthesized through a borrowing‐hydrogen mechanism. Up to 99 % isolated yields were obtained under relatively mild conditions without additive organic ligand. The catalytic process shows promise for the efficient and economic synthesis of amine, carboxamide, sulfonamide, and ketone derivatives because of the simplicity of the

  复杂且昂贵的有机配体通常在制备或工业水平的精细化学合成中必不可少。通过使用不具有添加剂有机配体的非均相催化剂体系来合成精细化学品是非常合乎需要的，但由于它们的通用性差和严格的反应条件而受到严格限制。在这里，我们显示了具有特定Ag 6 Mo 10 O 33的Ag / Mo杂化材料催化形成碳-氮或碳-碳键的结果晶体结构。通过借氢机制成功合成了48种含氮或氧的化合物，即胺，羧酰胺，磺酰胺和酮。在没有添加剂有机配体的条件下，在相对温和的条件下可获得高达99％的分离产率。催化过程显示出胺，羧酰胺，磺酰胺和酮衍生物的高效经济合成的希望，因为该系统简单且易于操作。
• Efficient and Clean Gold-Catalyzed One-Pot Selective N-Alkylation of Amines with Alcohols
  作者：Lin He、Xia-Bing Lou、Ji Ni、Yong-Mei Liu、Yong Cao、He-Yong He、Kang-Nian Fan

  DOI：10.1002/chem.201001848

  日期：2010.12.17

  Atom‐efficient direct N‐alkylation: An environmentally clean one‐pot selective N‐alkylation of amines with an equimolar amount of alcohols via a hydrogen autotransfer pathway was achieved over a titania‐supported gold catalyst system in good to excellent yields without additive (see scheme).

  原子有效的直接N烷基化：在二氧化钛负载的金催化剂体系上，通过无水氢的自动转移途径，通过等摩尔的醇与胺等摩尔环境下的纯N烷基选择性N-烷基化反应，在没有添加剂的情况下，收率良好至优异（参见方案）。
• Efficient nickel-catalysed<i>N</i>-alkylation of amines with alcohols
  作者：Anastasiia Afanasenko、Saravanakumar Elangovan、Marc C. A. Stuart、Giuseppe Bonura、Francesco Frusteri、Katalin Barta

  DOI：10.1039/c8cy01200h

  日期：——

  selective N-alkylation of amines with alcohols, that is in situ generated from Ni(COD)2 and KOH under ligand-free conditions. This novel method is very efficient for the functionalization of aniline and derivatives with a wide range of aromatic and aliphatic alcohols as well as diols and exhibits excellent functional group tolerance including halides, benzodioxane and heteroaromatic groups. Several TEM measurements

  通过借用氢策略使胺与醇选择性地进行N烷基化反应是一种突出的可持续催化方法，该方法产生水作为唯一的副产物，非常适合可广泛衍生自可再生能源的醇反应伙伴的催化转化资源。集中研究致力于开发主要基于昂贵的贵金属的新型催化剂。但是，用于这种转化的均相或非均相非贵金属催化剂的可用性非常有限。本文中，我们提出了一种高活性且非常易于制备的镍基催化剂体系，用于将胺与醇选择性地进行N-烷基化，该反应是就地进行的。在无配体条件下由Ni（COD）2和KOH生成。这种新方法对于苯胺及其衍生物与各种芳香族和脂肪族醇以及二醇的官能化非常有效，并且具有出色的官能团耐受性，包括卤化物，苯并二恶烷和杂芳族基团。为了结合活性催化剂的性质和影响反应活性的因素，进行了几种TEM测量和元素分析的结合。
• A Simple Cobalt(II) Chloride Catalyzed N-Alkylation of Amines with Alcohols
  作者：Siba Midya、Akash Mondal、Ayesha Begum、Ekambaram Balaraman

  DOI：10.1055/s-0036-1589064

  日期：2017.9

  Synthesis Abstract A facile cobalt-catalyzed N-alkylation of amines with alcohols using inexpensive, commercially available CoCl2·6H2O is reported. Employing this readily available cobalt catalyst, a variety of amines with wide functional group tolerance were selectively alkylated under benign conditions. A facile cobalt-catalyzed N-alkylation of amines with alcohols using inexpensive, commercially available

  献给大卫·米尔斯坦教授在他的70之际个生日 作为有机合成中的专题钴的一部分出版 抽象的 据报道，使用廉价的可商购的CoCl 2 ·6H 2 O ，用醇容易地进行钴的胺催化的N-烷基化。利用这种容易获得的钴催化剂，在良性条件下选择性地烷基化了多种具有宽泛的官能团耐受性的胺。 据报道，使用廉价的可商购的CoCl 2 ·6H 2 O ，用醇容易地进行钴的胺催化的N-烷基化。利用这种容易获得的钴催化剂，在良性条件下选择性地烷基化了多种具有宽泛的官能团耐受性的胺。
• Heterogeneous Ni Catalysts for N-Alkylation of Amines with Alcohols
  作者：Ken-ichi Shimizu、Naomichi Imaiida、Kenichi Kon、S. M. A. Hakim Siddiki、Atsushi Satsuma

  DOI：10.1021/cs4001267

  日期：2013.5.3

  Ni/θ-Al2O3, which suggests the cooperation of the acid–base site of θ-Al2O3. For a series of Ni/θ-Al2O3 catalysts with different particle size, the turnover frequency (TOF) per surface Ni increases with decreasing Ni mean particle size, indicating that low-coordinated Ni species and/or metal–support interface are active sites. From these results, we propose that the active site for this reaction is metal–support

  已经制备了负载在各种载体上的镍纳米颗粒（Ni / MO x），并研究了胺与醇的N-烷基化反应。在这些催化剂中，镍/θ-Al系2 Ó 3通过原位H制备2的NiO -还原/θ-Al系2 ö 3烷烃具有最高的活性，在无添加剂条件下，它是苯胺和脂族胺与各种醇（苄基和脂族醇）的烷基化反应的可重复使用的多相催化剂。伯胺被转化为仲胺，仲胺被转化为叔胺。对于苯胺与脂肪醇的反应，该催化剂比基于贵金属的最新催化剂显示出更高的周转数（TON）。机理研究表明，反应是通过氢借入机理进行的。Ni催化剂的活性取决于载体材料的性质。酸碱双功能载体比碱性或酸性载体具有更高的活性，这表明载体上的酸碱位点是必需的。2 Ó 3，这表明θ-Al的酸-碱位点的合作2 Ó 3。对于一系列的Ni /的θ-Al系2 ö 3种催化剂具有不同的颗粒大小，转换频率（TOF）每面的Ni增加随镍平均粒径，这表明低配位的Ni物种和/或金属-支撑界面是