N,N-Dibutyl-4-chlorobenzenamine | 67655-26-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-Dibutyl-4-chlorobenzenamine
• 英文别名: N,N-dibutyl-4-chloroaniline；N,N-dibutyl-p-chloroaniline
• CAS: 67655-26-9
• 化学式: C₁₄H₂₂ClN
• 分子量: 239.788
• InChiKey: BCAHAACEAZKVCH-UHFFFAOYSA-N

物化性质

• 沸点：
  107-112 °C(Press: 0.28 Torr)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-Dibutyl-4-chlorobenzenamine 在 正丁基锂 、 N-propylpropylene urea 、 samarium diiodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以83%的产率得到N,N-二丁基苯胺
  参考文献：
  名称：

  尿酸盐作为二碘化mar活化剂的用途

  摘要：

  已经开发了使用尿酸盐作为反应促进剂的SmI 2活化的新模式。已经显示出通过用正丁基锂处理相应的脲而形成的几种脲酸酯在很大程度上活化了SmI 2，从而还原了1-氯癸烷。由SmI 2和各种脲酸酯形成的络合物已显示可用于减少各种有机卤化物，包括低反应性的底物，如芳基氟化物。由于易于合成且分子量低，因此，三乙基脲的共轭碱（TEU –）成为主要关注对象。可见光谱和反应性数据与以下假设相符：在SmI 2时会形成相同的络合物被结合的TEU 2或4当量- ，尽管SMI的更大反应性的2 /4 TEU -一些烷基卤。我们认为活性还原剂是SmI 2和2当量TEU –之间形成的N，O螯合物。

  DOI：

  10.1021/acs.joc.6b00733
• 作为产物：
  描述：

  氯丁烷 、 对氯苯胺 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 23.0h， 以90%的产率得到N,N-Dibutyl-4-chlorobenzenamine
  参考文献：
  名称：

  Silica-Functionalized CuI: An Efficient and Selective Catalyst for N-Benzylation, Allylation, and Alkylation of Primary and Secondary Amines in Water

  摘要：

  Silica-functionalized CuI has been reported as an efficient and selective catalyst for the selective mono-N- and N,N-dibenzylation, allylation, and alkylation of primary amines with benzylic, allylic, and alkyl halides using NaOH as base in aqueous medium. By changing the reaction temperature, mono- or di-benzylation, allylation, or alkylation could be achieved in good yield and selectivity. Secondary amines have also been benzylated, allylated, and alkylated under similar conditions. SiO2-CuI has been characterized by Fourier transform-infrared, atomic absorption spectrometry, thermalgravimetric analysis, X-ray diffraction, scanning electron microscopy, and transmission electron microscopy, and found to be highly selective and recyclable under the reaction conditions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.828077

文献信息

• The Transition Metal-catalyzed<i>N</i>-Alkylation and<i>N</i>-Heterocyclization. A Reductive Transformation of Nitroarenes into (Dialkylamino)arenes and 2,3-Dialkyl-substituted Quinolines Using Aliphatic Aldehydes under Carbon Monoxide
  作者：Yoshihisa Watanabe、Naoki Suzuki、Yasushi Tsuji、Sang Chul Shim、Take-aki Mitsudo

  DOI：10.1246/bcsj.55.1116

  日期：1982.4

  The catalytic N-alkylation and N-heterocyclization of nitroarenes occur at 180 °C under a carbon monoxide pressure of 70 atm and in the presence of aldehyde and such transitionmetal complexes as rh...

  硝基芳烃的催化 N-烷基化和 N-杂环化在 180°C 和 70 个大气压的一氧化碳压力下，在醛和诸如铑等过渡金属配合物的存在下发生。
• Solvent/metal-free benzimidazolium-based carboxyl-functionalized porphyrin photocatalysts for the room-temperature alkylation of amines under the irradiation of visible light
  作者：Subodh Uttamrao Raut、Kamlesh Rudreshwar Balinge、Shubham Avinash Deshmukh、Shital Haribhau Barange、Bhairav Chandroday Mataghare、Pundlik Rambhau Bhagat

  DOI：10.1039/d2cy00846g

  日期：——

  morpholine, and various alcohols, with water being the only by-product. The metal-free protocol was further supported by the ICP-OES data, indicating the negligible quantity of Pd/Ru in the photocatalyst and the product. The photocatalytic competence was studied under ambient conditions using 5 W LED light with high stability and substantial reusability for six runs without significant loss in the yield of alkylated

  改进用于绿色化学生产的新型可持续催化方法是化学科学中的一个新兴领域。在此，首次开发了一种可持续的催化工艺，用于直接N- 在 LED 灯存在的情况下，在自制的光催化反应器中，使用高效的无金属苯并咪唑基羧基官能化卟啉 (MFBBCFPc) 多相光催化剂将伯胺和仲胺与醇进行烷基化。在这种情况下，目前的协议证明了无金属条件可耐受广泛的底物范围，包括伯胺、苯二胺和二级胺，如吡咯、吗啉和各种醇，水是唯一的副产品。ICP-OES 数据进一步支持了无金属方案，表明光催化剂和产品中 Pd/Ru 的量可忽略不计。在环境条件下使用 5 W LED 灯研究了光催化能力，该灯具有高稳定性和基本可重复使用性，可重复使用六次，而不会显着损失烷基化产物的产率。烷基化胺的形成进行通过(i) 在 MFBBCFPc 光催化剂表面上醇的氧化形成醛和 (ii) 胺与光催化剂表面上的醛缩合，然后通过表面上的氢原子氢化所得亚胺MFBBCFPc。
• Chemoselective synthesis of tertiary and secondary amines by reductive amination of aldehydes
  作者：Wan-Jin Xiong、Lei Li、Jiang-Tao Li、Shi-Qiang Zhang、Jun-Lei Tang、Taigang Zhou

  DOI：10.1016/j.tetlet.2023.154684

  日期：2023.9

  A simple and efficient catalyst-free chemoselective reductive amination of primary amines and aldehydes to synthesis of tertiary and secondary amines with borane complex was developed. Primary amines are converted into tertiary and secondary amines in one pot reaction under mild condition with good functional group compatibility and It does not require any catalyst to participate in this reaction.

  开发了一种简单高效的无催化剂化学选择性还原胺化伯胺和醛，以与硼烷配合物合成叔胺和仲胺。伯胺转化为叔胺和仲胺的一锅反应条件温和，官能团相容性好，并且不需要任何催化剂参与该反应。通过改变硼烷络合物的空间位阻来实现化学选择性控制。该策略成功应用于合成丁卡因（麻醉剂），并通过同位素标记实验验证了其潜在机制。
• Thermosetting powder coating material and coated article
  申请人：FUJI XEROX CO., LTD.

  公开号：US10040949B2

  公开（公告）日：2018-08-07

  A thermosetting powder coating material includes powder particles containing a mixture of a vinyl resin A including a block isocyanate group and a carboxyl group and a vinyl resin B including a hydroxyl group and a carboxyl group, or a vinyl resin C including a block isocyanate group, a hydroxyl group and a carboxyl group, wherein a content of the isocyanate group is from 0.4 mmol/g to 1.4 mmol/g, and a functional group molar ratio of [NCO/(COOH+OH)], which is obtained by dividing the content of the isocyanate group by a total content of the hydroxyl group and the carboxyl group, is from 0.5 to 1.2.

  一种热固性粉末涂料材料包括含有乙烯基树脂 A（包括异氰酸酯嵌段基团和羧基）和乙烯基树脂 B（包括羟基和羧基）或乙烯基树脂 C（包括异氰酸酯嵌段基团、羟基和羧基）混合物的粉末颗粒，其中异氰酸酯基团的含量为 0.4 mmol/g 至 1.4 mmol/g，官能团摩尔比[NCO/(COOH+OH)]为 0.5 至 1.2，该摩尔比由异氰酸酯基的含量除以羟基和羧基的总含量得出。
• Functionalized ionic liquids based on imidazolium cation: Synthesis, characterization and catalytic activity for N-alkylation reaction
  作者：Serpil Demir、Yunus Damarhan、İsmail Özdemir

  DOI：10.1016/j.molliq.2015.01.051

  日期：2015.4

  The novel functionalized ionic liquids based on imidazolium cation are synthesized and characterized by studying its H-1, C-13, and P-31 NMR and elemental analysis. These ionic liquids have been reported as a highly efficient catalyst for N-alkylation reaction of aniline with butyl chloride. The reaction was efficiently performed in ionic liquid as an environmentally benign solvent with good yields without transition metal. (C) 2015 Elsevier B.V. All rights reserved.