5,6-dimethyl-2-(4-pyridylmethyl)-1H-benzimidazole | 141763-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5,6-dimethyl-2-(4-pyridylmethyl)-1H-benzimidazole
• 英文别名: 5,6-dimethyl-2-(pyridin-4-ylmethyl)-1H-benzimidazole
• CAS: 141763-02-2
• 化学式: C₁₅H₁₅N₃
• 分子量: 237.304
• InChiKey: NFZFQYAXBSNEPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-2-(4-pyridylmethyl)-1H-benzimidazole 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以38%的产率得到(5,6-Dimethyl-1H-benzoimidazol-2-yl)-pyridin-4-yl-methanone
  参考文献：
  名称：

  Unconventional acceptor and donor functional groups linked by a captodative spacer

  摘要：

  The chemical stability to oxidation of a set of compounds built up from acceptor and donor subunits linked by a methylene or a hydroxymethylene group was studied. Whereas 1-butyl-3-[1,2,4-triazol-5(3)-ylmethyl]pyridinium salts 2d,e showed high stability to oxidation, 1-butyl-4-[imidazol-4(5)-ylhidroxymethyl]pyridinium salt 14f was oxidised spontaneously to the corresponding carbonyl compound, indicating the capability of the oxidation phenomenon to be controlled by the nature of the building blocks. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00968-4
• 作为产物：
  描述：

  吡啶-4-乙酸甲酯 、 4，5-二甲基-1，2-苯二胺 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 2.5h， 以75%的产率得到5,6-dimethyl-2-(4-pyridylmethyl)-1H-benzimidazole
  参考文献：
  名称：

  An Advantageous Synthesis of 2-Substituted Benzimidazoles Using Polyphosphoric Acid. 2-(Pyridyl)-1H-benzimidazoles, 1-Alkyl-(1H-benzimidazol-2-yl)pyridinium Salts, their Homologues and Vinylogues

  摘要：

  标题中的 2-取代的苯并咪唑是通过高效的一锅程序制备的，即相应的可获得的羧酸和 1,2-芳二胺在菲利普斯苯并咪唑合成中发现的缩合类型中，使用多磷酸作为催化剂和溶剂进行环脱水反应。该方法经改良后证明对具有亚甲基和亚乙烯环间分子的 1-烷基-(1H-苯并咪唑-2-基)吡啶鎓四氟硼酸盐非常有用。

  DOI：

  10.1055/s-1992-26121

文献信息

• Design of unusual captodative methylene substrates: 1-Alkyl-4(3)-(azolylmethyl)pyridinium salts 1
  作者：Ermitas Alcalde、Maria Gisbert、Lluïsa Pérez-García

  DOI：10.1016/0040-4020(95)00850-8

  日期：1995.11

  functional groups of several examples of 1-alkyl-4(3)-(1H-azolylmethyl) pyridinium salts 1 and 2 exemplifies a concomitant application of the arenoanalogy principle and the captodative effect in organic synthesis. A remarkably driving force by the nature of non-classical acceptor and donor heteroaromatic rings is observed upon the chemical behavior of the title compounds 1 and 2, modulating the susceptibility

  与1-烷基-4（3）-（1 H-偶氮基甲基）吡啶鎓盐1和2的几个实例的己内酰胺（受体）和供体非经典官能团连接的碳原子的前所未有的自发氧化，例举了同时应用在有机合成中的种类学原理和俘获作用。在标题化合物1和2的化学行为上观察到非经典受体和供体杂芳族环的性质产生的显着驱动力，调节了亚甲基间隔基氧化成它们的氧甲基对应物5和6的敏感性。获得偶极1-烷基-3-吡啶碘甲基-3（5）-1,2,4-三唑盐内盐4 已实现。
• Novel captodative methylene compounds. Spontaneous oxidation of 1-alkyl-4(3)-(azolylmethyl)pyridinium salts
  作者：Ermitas Alcalde、Maria Gisbert、Lluïsa Pérez-García

  DOI：10.1039/c39940000981

  日期：——

  For several examples of the title compounds 4–7 and 12 the nature of the non-classical acceptor and donor heteroaromatic moieties modulates the susceptability of the methylene spacer towards oxidation.

  对于标题化合物4-7和12的几个例子，非经典受体和供体杂芳族基团的性质调节了亚甲基间隔基对氧化的敏感性。
• Alcalde Ermitas, Gisbert Maria, Perez-Garcia Lluiesa, J. Chem. Soc. Chem. Commun, (1994) N 8, S 981-982
  作者：Alcalde Ermitas, Gisbert Maria, Perez-Garcia Lluiesa

  DOI：——

  日期：——
• An Advantageous Synthesis of 2-Substituted Benzimidazoles Using Polyphosphoric Acid. 2-(Pyridyl)-1<i>H</i>-benzimidazoles, 1-Alkyl-(1<i>H</i>-benzimidazol-2-yl)pyridinium Salts, their Homologues and Vinylogues
  作者：Ermitas Alcalde、Immaculada Dinarés、Lluïsa Pérez-García、Tomàs Roca

  DOI：10.1055/s-1992-26121

  日期：——

  The title 2-substituted benzimidazoles are prepared by a highly efficient one-pot procedure, cyclodehydration of the corresponding accessible carboxylic acids and 1,2-arylenediamines, using polyphosphoric acid as the catalyst and solvent in a condensation of the type found in the Phillips benzimidazole synthesis. The method has been adapted and proved to be extremely useful for 1-alkyl-(1H-benzimidazol-2-yl) pyridinium tetrafluoroborates with a methylene and vinylene interannular moiety.

  标题中的 2-取代的苯并咪唑是通过高效的一锅程序制备的，即相应的可获得的羧酸和 1,2-芳二胺在菲利普斯苯并咪唑合成中发现的缩合类型中，使用多磷酸作为催化剂和溶剂进行环脱水反应。该方法经改良后证明对具有亚甲基和亚乙烯环间分子的 1-烷基-(1H-苯并咪唑-2-基)吡啶鎓四氟硼酸盐非常有用。
• Unconventional acceptor and donor functional groups linked by a captodative spacer
  作者：Ermitas Alcalde、Maria Gisbert、Josep M. Pons、Lluïsa Pérez-Garcia

  DOI：10.1016/s0040-4020(96)00968-4

  日期：1996.11

  The chemical stability to oxidation of a set of compounds built up from acceptor and donor subunits linked by a methylene or a hydroxymethylene group was studied. Whereas 1-butyl-3-[1,2,4-triazol-5(3)-ylmethyl]pyridinium salts 2d,e showed high stability to oxidation, 1-butyl-4-[imidazol-4(5)-ylhidroxymethyl]pyridinium salt 14f was oxidised spontaneously to the corresponding carbonyl compound, indicating the capability of the oxidation phenomenon to be controlled by the nature of the building blocks. Copyright (C) 1996 Elsevier Science Ltd