N⁴,N⁴,N^4',N^4',2,2',6,6'-octamethyl-[1,1'-biphenyl]-4,4'-diamine | 22409-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁴,N⁴,N^4',N^4',2,2',6,6'-octamethyl-[1,1'-biphenyl]-4,4'-diamine
• 英文别名: N,N,N′,N′-tetramethyl-2,2′,6,6′-tetramethylbenzidine；N,N,N',N',2,2',6,6'-octamethylbenzidine；4,4'-Bis--2,6,2',6'-tetramethyl-biphenyl；4,4'-Bis-(dimethylamino)-2,2',6,6'-tetramethylbiphenyl；4,4'-Bis-(dimethylamino)-2,6,2',6'-tetramethyl-biphenyl；4-[4-(dimethylamino)-2,6-dimethylphenyl]-N,N,3,5-tetramethylaniline
• CAS: 22409-73-0
• 化学式: C₂₀H₂₈N₂
• 分子量: 296.456
• InChiKey: KKASTZBEWCTVHV-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C(Solv: ethanol (64-17-5))
• 沸点：
  409.3±45.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N,3,5-四甲基苯胺 在 5% rhodium-on-charcoal 、 三氟乙酸 作用下， 反应 2.0h， 以72%的产率得到N⁴,N⁴,N^4',N^4',2,2',6,6'-octamethyl-[1,1'-biphenyl]-4,4'-diamine
  参考文献：
  名称：

  苯胺催化和好氧氧化联芳基偶联使用可回收的多相催化剂合成联苯胺和联咔唑

  摘要：

  在这项研究中，报道了利用分子氧作为唯一氧化剂的苯胺铑的多相催化氧化均偶联反应。使用市售可回收的Rh / C催化剂能够使各种苯胺，包括N，N-二取代和N-单取代的苯胺，以及二芳基胺，三芳基胺和咔唑进行氧化二聚。此外，催化方案扩展到苯胺的邻-邻偶联，从而获得具有高区域选择性的2,2'-二氨基联苯。值得注意的是，已开发的方法可以以操作简单，实用且环境友好的方式快速访问各种功能化的联苯胺和二氨基联苯。

  DOI：

  10.1021/acs.joc.0c02020

文献信息

• Electrochemical dehydrogenative cross-coupling of two anilines: facile synthesis of unsymmetrical biaryls
  作者：Mu-Jia Luo、Yang Li、Xuan-Hui Ouyang、Jin-Heng Li、De-Liang He

  DOI：10.1039/c9cc09879h

  日期：——

  A new, general ortho/para-selective anodic dehydrogenative cross-coupling of two aryl amines, naphthalen-2-amine derivatives and anilines, is described. This electrochemical protocol assembles a wide range of unsymmetrical biaryls in good to excellent yields under mild, additional-metal-catalyst-free, oxidant-free conditions with excellent selectivity, broad substrate scope, and wide functional group

  描述了两种芳基胺，萘-2-胺衍生物和苯胺的新的一般的邻/对选择性阳极脱氢交叉偶联。该电化学方案可在温和的，无附加金属催化剂，无氧化剂的条件下，以优异的选择性，宽泛的底物范围和宽泛的官能团耐受性，以良好的产率组装各种不对称的联芳基。通过将重要的药效基团容易地掺入到最终的联芳基中，这一电化学技术得到了突显，并且适用于苯胺的均偶联以生产对称的联芳基。
• PHOTOPOLYMERIZABLE COMPOSITIONS FEATURING NOVEL AMINE ACCELERATOR FOR IMPROVED COLOR STABILITY AND REDUCED POLYMERIZATION STRESS THEREBY
  申请人：DENTSPLY SIRONA INC.

  公开号：US20160228334A1

  公开（公告）日：2016-08-11

  A photopolymerization accelerator composition improving color stability and controlling polymerization shrinkage stress of cured resin and/or the resulting composite paste thereby feature by tertiary twisted biphenyldiamine with the general formula I: R2 and R3 are each independently alkyl having from 1 to 5 carbon atoms; R and R1 are each independently hydrogen or halogen; alkyl, alkoxy, or alkylthio having from 1 to 18 carbon atoms; or phenyl and/or substituted phenyl alkoxy, or alkylthio having from 1 to 18 carbon atoms. It can be used in part with conventional photosensitizers and radically polymerizable monomers.

  一种光聚合加速剂组合物，可以改善固化树脂的颜色稳定性，控制聚合收缩应力，以及由此产生的复合糊的特性，其特点是含有三级扭曲联苯二胺，其通式为I：R2和R3分别独立为具有1至5个碳原子的烷基；R和R1分别独立为氢或卤素；烷基、烷氧基或烷硫基，其碳原子数为1至18；或苯基和/或取代苯基烷氧基或烷硫基，其碳原子数为1至18。它可以与传统的光敏剂和自由基聚合单体部分配合使用。
• Extension studies on iron(III)-promoted free radical oxidation of anilines: self-coupling and self-bridged assembling reactions
  作者：Jing Pan、Jiaqiang Li、Ruofeng Huang、Xiaohui Zhang、Hang Shen、Yan Xiong、Xiangming Zhu

  DOI：10.1016/j.tet.2015.06.018

  日期：2015.8

  The iron(III)-promoted free radical oxidation of anilines has been further developed. Anilines including those bearing strong electron-withdrawing groups on benzene ring were readily converted into corresponding self-coupling benzidines. With addition of base, the methyl on nitrogen was activated and the free radical oxidations tended to furnish the corresponding self-bridged assembling diaminodiarylmethanes. (C) 2015 Elsevier Ltd. All rights reserved.
• Naphthalene-1,8-diylbis(diphenylmethylium) as an Organic Two-Electron Oxidant:  Benzidine Synthesis via Oxidative Self-Coupling of <i>N,N</i>-Dialkylanilines
  作者：Terunobu Saitoh、Suguru Yoshida、Junji Ichikawa

  DOI：10.1021/jo060662s

  日期：2006.8.1

  Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N, N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.
• 1,8-Bis(diphenylmethylium)naphthalenediyl Dication as an Organic Oxidant:  Synthesis of Benzidines via Self-Coupling of <i>N,N</i>-Dialkylanilines
  作者：Terunobu Saitoh、Suguru Yoshida、Junji Ichikawa

  DOI：10.1021/ol048058w

  日期：2004.11.1

  1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.