4-((dibenzylamino)methyl)benzonitrile | 1216942-16-3

• 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: 4-((dibenzylamino)methyl)benzonitrile
• 英文别名: N-(4-cyanobenzyl)-N,N-dibenzylamine；4-[(Dibenzylamino)methyl]benzonitrile；4-[(dibenzylamino)methyl]benzonitrile
• CAS: 1216942-16-3
• 化学式: C₂₂H₂₀N₂
• mdl: MFCD30223556
• 分子量: 312.414
• InChiKey: AZDRJOSVPSQPJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.136
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((dibenzylamino)methyl)benzonitrile 、 C.I.酸性橙108 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以47%的产率得到N,N-dibenzyl-1-(4-(4,5-dihydrooxazol-2-yl)phenyl)-methanamine
  参考文献：
  名称：

  Synthesis of 2-Aryl/Heteroaryloxazolines from Nitriles under Metal- and Catalyst-Free Conditions and Evaluation of Their Antioxidant Activities

  摘要：

  The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.

  DOI：

  10.1021/jo501430p
• 作为产物：
  描述：

  n-苄基苯甲酰胺 在 bis(trimethylsilyl)amide yttrium(III) 、 三乙胺 、 频那醇硼烷 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 4-((dibenzylamino)methyl)benzonitrile
  参考文献：
  名称：

  钇配合物的同质双（三甲基甲硅烷基）酰胺催化酰胺的硼氢化还原。

  摘要：

  均一的镧系元素络合物Y [N（TMS）2] 3是一种高效的均相催化剂，可用于将硼化的仲酰胺和叔酰胺还原为相应的胺。发现一系列含有不同官能团如氰基，硝基和乙烯基的酰胺具有良好的耐受性。该转化也已经很好地应用于吲哚和吡哌贝地的合成。详细的同位素标记实验，对照实验和动力学研究为阐明反应机理提供了累积的证据。

  DOI：

  10.1021/acs.orglett.9b04606

文献信息

• Efficient and Selective Hydrosilylation of Secondary and Tertiary Amides Catalyzed by an Iridium(III) Metallacycle: Development and Mechanistic Investigation
  作者：Yann Corre、Xavier Trivelli、Frédéric Capet、Jean-Pierre Djukic、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1002/cctc.201700400

  日期：2017.6.8

  Readily accessible cationic IrIII metallacycles catalyze efficiently the chemoselective hydrosilylation of tertiary and secondary amides to amines. The catalyst described herein operates at low loadings using inexpensive 1,1,3,3-tetramethyldisiloxane and allows fast reactions with high yields, selectivities, and turnover numbers. A transient iminium intermediate has been observed for the first time

  易于获得的阳离子Ir III金属环有效催化叔酰胺和仲酰胺向胺的化学选择性氢化硅烷化。本文所述的催化剂使用廉价的1,1,3,3-四甲基二硅氧烷在低负荷下操作，并允许以高产率，选择性和周转数进行快速反应。通过质谱法首次观察到了过渡亚胺鎓中间体，并通过DFT计算研究了催化剂和硅烷试剂的活化。这些基本见解通过适当的配体修饰来支持Ir III金属环的当前和未来的改进，并使基于金属环的催化剂能够进一步广泛应用。
• One-Pot Reductive N-Alkylation with Carbonyl Compounds To Give Tertiary Amines via Borane Reduction of Imines
  作者：Tetsuo Ohta、Masashi Tokizane、Kaori Sato、Yuki Sakami、Yoichiro Imori、Chika Matsuo、Yoshihiko Ito

  DOI：10.1055/s-0029-1217076

  日期：2010.1

  borane-mediated reduction of imines and reductive N-alkylation with carbonyl compounds is described. This protocol’s reducing agent is only borane in the reduction of imines, and additional reductant is not necessary in reductive N-alkylation step. When using more than two equivalents of aldehydes, reductive N-alkylation proceeded in good yield. reductive N-alkylation - borane reduction - imines - tertiary

  描述了通过硼烷介导的亚胺还原和羰基化合物的还原性N-烷基化来一锅合成叔胺。该方案的还原剂在亚胺的还原中仅是硼烷，在还原性N-烷基化步骤中不需要其他还原剂。当使用多于两个当量的醛时，还原性N-烷基化以良好的产率进行。 还原性N-烷基化-硼烷还原-亚胺-叔胺-一锅反应
• Visible‐Light‐Mediated Aromatic Substitution Reactions of Cyanoarenes with 4‐Alkyl‐1,4‐dihydropyridines through Double Carbon–Carbon Bond Cleavage
  作者：Kazunari Nakajima、Sunao Nojima、Ken Sakata、Yoshiaki Nishibayashi

  DOI：10.1002/cctc.201600037

  日期：2016.3.18

  photoredox catalyst proceed smoothly to give the corresponding alkyl‐substituted arenes in good to high yields. The present reaction system realizes a novel C−C bond‐forming reaction between two fragments generated from the C−C bond‐cleavage reactions of two independent substrates.

  在催化量的光氧化还原催化剂存在下，氰基芳烃与4-烷基-1,4-二氢吡啶作为烷基化试剂的新型芳族取代反应可以顺利进行，从而以高至高收率得到相应的烷基取代的芳烃。本反应体系实现了两个独立底物的C-C键断裂反应产生的两个片段之间的新型C-C键形成反应。
• Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines
  作者：Pengqing Ye、Yinlin Shao、Xuanzeng Ye、Fangjun Zhang、Renhao Li、Jiani Sun、Beihang Xu、Jiuxi Chen

  DOI：10.1021/acs.orglett.9b04606

  日期：2020.2.21

  Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed

  均一的镧系元素络合物Y [N（TMS）2] 3是一种高效的均相催化剂，可用于将硼化的仲酰胺和叔酰胺还原为相应的胺。发现一系列含有不同官能团如氰基，硝基和乙烯基的酰胺具有良好的耐受性。该转化也已经很好地应用于吲哚和吡哌贝地的合成。详细的同位素标记实验，对照实验和动力学研究为阐明反应机理提供了累积的证据。
• Synthesis of 2-Aryl/Heteroaryloxazolines from Nitriles under Metal- and Catalyst-Free Conditions and Evaluation of Their Antioxidant Activities
  作者：Parul Garg、Shweta Chaudhary、Marilyn D. Milton

  DOI：10.1021/jo501430p

  日期：2014.9.19

  The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.