N,N'-dibenzyl-m-phenylenediamine | 111283-70-6

• 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: N,N'-dibenzyl-m-phenylenediamine
• 英文别名: N¹,N³-dibenzylbenzene-1,3-diamine；N,N'-dibenzylbenzene-1,3-diamine；1-N,3-N-dibenzylbenzene-1,3-diamine
• CAS: 111283-70-6
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: RGSLUNYPVJQYPO-UHFFFAOYSA-N

物化性质

• 熔点：
  71.5-72.5 °C
• 沸点：
  471.8±33.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-dibenzyl-m-phenylenediamine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 38.5h， 生成 2,20-Dibenzyl-5,17-dichloro-2,4,6,8,14,16,18,20,26,28-decazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene
  参考文献：
  名称：

  Synthesis of Tetraazacalix[2]arene[2]triazines:  Tuning the Cavity by the Substituents on the Bridging Nitrogen Atoms

  摘要：

  A number of tetraazacalix[ 2] arene[ 2] triazines bearing different substituents on the bridging nitrogen atoms were synthesized efficiently using a fragment coupling strategy. The N- arylation of the parent azacalix[ 2] arene[ 2] triazine afforded tetra( arylaza) calix[ 2] arene[ 2] triazine in 91% yield. The introduction of different substituents on the bridging positions led to the regulation of the cavity of the resulting macrocyclic molecules.

  DOI：

  10.1021/ol062441e
• 作为产物：
  描述：

  (1E,1'E)-N,N'-(1,3-phenylene)bis(1-phenylmethanimine) 在 sodium tetrahydroborate 、 溶剂黄146 、 水 、 碳酸氢钠 作用下， 以 苯 为溶剂， 以94%的产率得到N,N'-dibenzyl-m-phenylenediamine
  参考文献：
  名称：

  Synthesis of N,N′-bis-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)-phenylmethylene- and -Phenylmethyl]-1,3-phenylenediamines

  摘要：

  Starting with the vanillin series aldehydes, by reaction with 1,3-phenylenediamine in absolute methanol E,E-N,N'-bis-[3-alkoxy-4-(hydroxy-, alkoxy-, acyloxy)phenylme-thylene]-1,3-phenyl-enediamines (Shiff bases) are synthesized from reduction with Na[BH(OAc)(3)] in benzene were prepared respective N,N'-bis-[3-alkoxy-4-(hydroxy-, alkoxy-, acyloxy)phenylmethyl]-1,3-phenyl-enediamines.

  DOI：

  10.1134/s1070363209020157

文献信息

• The Iridium-Catalyzed Synthesis of Symmetrically and Unsymmetrically Alkylated Diamines under Mild Reaction Conditions
  作者：Stefan Michlik、Toni Hille、Rhett Kempe

  DOI：10.1002/adsc.201100554

  日期：2012.3.16

  An iridium catalyst – stabilized by an anionic P,N ligand – was used for the symmetrical and unsymmetrical monoalkylation of para‐, meta‐, and ortho‐benzenediamines. Benzyl and aliphatic alcohols were used as alkylating reagents. 28 derivatives were synthesized. 14 of them are new compounds. Furthermore, the alkylation of the pharmacological important diamine Dapson® (dapsone) is described. 14 dapsone

  铱催化剂-通过阴离子P稳定，N配体-用于的对称和非对称单烷基化对位- ，间位-和邻-benzenediamines。苄基和脂族醇用作烷基化试剂。合成了28种衍生物。其中14种是新化合物。此外，药理学重要的二胺Dapson的烷基化®（氨苯砜）进行说明。合成了14种氨苯砜衍生物，其中9种为新化合物。
• Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
  作者：Keshav Paudel、Shi Xu、Oleksandr Hietsoi、Bedraj Pandey、Chuka Onuh、Keying Ding

  DOI：10.1021/acs.organomet.0c00727

  日期：2021.2.8

  Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading

  本文介绍了由三脚架配体支撑的明确定义的钴配合物催化的可转换亚胺和胺合成。各种各样的伯醇和胺以良好至极好的收率选择性地转化为亚胺或胺。发现该碱在选择性上起关键作用。催化量的碱导致亚胺的形成，而碱的过量负载导致胺产物。这种关于产物选择性的策略也强烈地取决于所使用的有机金属催化剂。我们希望本研究可以为选择性有机合成和催化剂设计提供有用的见识。
• Room temperature and solvent-free iridium-catalyzed selective alkylation of anilines with alcohols
  作者：Jia-Qi Li、Pher G. Andersson

  DOI：10.1039/c3cc42669f

  日期：——

  A bidentate iridium NHC–phosphine complex has been developed and applied to the N-monoalkylation of aromatic amines with a wide range of primary alcohols and to the N-heterocyclization of amino alcohols. This reaction resulted in high isolated product yields, even at room temperature and under solvent-free conditions.

  一种双齿铱NHC-膦配体复合物已被开发并应用于广泛范围的伯醇与芳香胺的N-单烷基化反应和氨基酸醇的N-杂环化。该反应在室温下和无溶剂条件下均能产生高分离产物收率。
• Base-mediated cascade amidination/<i>N</i>-alkylation of amines by alcohols
  作者：Chunyan Zhang、Zuyu Liang、Fenghong Lu、Xiaofei Jia、Guoying Zhang、Mao-Lin Hu

  DOI：10.1039/d0cc04831c

  日期：——

  amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, 15N labeled

  已经开发了碱通过醇介导的胺的级联酰胺化/ N-烷基化反应。首次在N-烷基化中将腈鉴定为有效且良性的水受体试剂。值得注意的是，该方法可耐受一系列官能团，例如甲氧基，卤素，乙烯基和杂基，为构建不同的取代的二氨基化合物，15 N标记的胺提供了便利的方法，并且可以按比例放大至1 mol规模，可提供138.7 g一锅即可获得高收率的所需产品。机理研究为t -BuOK促进胺与腈酰胺化提供了有力的证据。
• Cobalt-Catalyzed Alkylation of Aromatic Amines by Alcohols
  作者：Sina Rösler、Michael Ertl、Torsten Irrgang、Rhett Kempe

  DOI：10.1002/anie.201507955

  日期：2015.12.7

  sustainable or green reaction that has received a lot of attention in recent years and is preferentially catalyzed by Ir or Ru complexes is the alkylation of amines by alcohols. It is based on the borrowing hydrogen or hydrogen autotransfer concept. Herein, we report on the Co‐catalyzed alkylation of aromatic amines by alcohols. The reaction proceeds under mild conditions, and selectively generates monoalkylated

  在典型的贵金属介导化学中实施廉价的，富含地球的金属是均相催化的主要目标。近年来，引起人们广泛关注并优先被Ir或Ru络合物催化的可持续或绿色反应是醇对胺的烷基化。它基于借用氢气或氢气自动转移的概念。本文中，我们报道了醇对芳香胺的共催化烷基化反应。该反应在温和的条件下进行，并选择性地产生单烷基化的胺。观察到的选择性允许合成不对称取代的二胺。由PN 5 P配体稳定的新型Co络合物最有效地催化反应。