2-(1H-1,3-benzimidazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile | 1262791-57-0

• 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: 2-(1H-1,3-benzimidazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile
• 英文别名: 2-(benzothiazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile；2-(1h-Benzo[d]imidazol-2-yl)-2-(tetrahydro-2-furanylidene)acetonitrile；2-(1H-benzimidazol-2-yl)-2-(oxolan-2-ylidene)acetonitrile
• CAS: 1262791-57-0
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: LSVXUOWMVZDCMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.0±55.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-1,3-benzimidazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile 在 四氢吡咯 作用下， 以 异丙醇 为溶剂， 以87%的产率得到2-氰甲基苯并咪唑
  参考文献：
  名称：

  Reaction of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with aldehydes

  摘要：

  The reaction of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with a electrophilic reagent (anisaldehyde) was studied. It was shown that condensation of the latter with 2-(4-oxo-3,4-dihydro-2-quinazolyl)- and 2-(1H-benzo[d]imidazol-2-yl)-2-(tetrahydro-2-furanylidene) acetonitriles in the presence of secondary amines or acids takes place with elimination of the furan fragment and the formation of 3-aryl-2-(4-oxo-3,4-dihydro-2-quinazolinyl)- and 2-(1H-benzo[d] imidazol-2-yl)acrylonitriles.

  DOI：

  10.1007/s10593-010-0604-0
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(1H-1,3-benzimidazol-2-yl)-2-(tetrahydro-2-furanyliden)acetonitrile
  参考文献：
  名称：

  Reaction of 2-Hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles with 1,3-N,N-Binucleophiles

  摘要：

  The reactions of 2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles with 1,3-N,N-binucleophiles have been investigated. The mechanisms of the reactions have been discussed. Domino reactions of 2-hetaryl-2-(tetrahydro-2-furanyliden) acetonitriles with amidines can provide an efficient access to 3-[2-substituted 6-amino-5-hetaryl-4-pyrimidinyl]-1-propanols.

  DOI：

  10.1055/s-0031-1290435

文献信息

• Hydroxypropyl substituted nitrogen bridgehead fused cyanopyridines
  作者：Demyd S. Milokhov、Olga V. Khilya、Alexander V. Turov、Volodymyr V. Medviediev、Oleg V. Shishkin、Yulian M. Volovenko

  DOI：10.1016/j.tet.2013.12.074

  日期：2014.2

  promoted Michael addition of the substituted acetonitriles to 2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles followed by ring transformations has provided novel convenient synthetic methods to nitrogen bridgehead fused cyanopyridines bearing hydroxypropyl side chain. The structures of obtained compounds have been established based on NMR spectroscopy investigation and X-ray diffraction data.

  研究了2-杂芳基-2-（四氢-2-呋喃二烯）乙腈与取代乙腈作为C-亲核试剂的反应，并提出了反应机理。碱促进的取代基乙氧基到2-杂芳基-2-（四氢-2-呋喃腈）乙腈的迈克尔加成反应，然后进行环转化，为带有羟基丙基侧链的氮桥头稠合氰基吡啶提供了新颖便捷的合成方法。基于NMR光谱学研究和X射线衍射数据，已经建立了获得的化合物的结构。
• Synthesis of 2-(2-hetaryl)-6-hydroxy-3-(R-amino)-2-hexenenitriles
  作者：O. V. Khilya、T. A. Volovnenko、A. V. Turov、R. I. Zubatyuk、O. V. Shishkin、Yu. M. Volovenko

  DOI：10.1007/s10593-013-1208-2

  日期：2013.3

  The reaction of 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles and 6-chloro-2-(2-hetarylidene)-3-oxohexanenitriles with amines was studied. It was shown that the reaction of primary aliphatic amines with 6-chloro-2-(2-hetarylidene)-3-oxohexanenitriles takes place through a stage involving the formation of 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles followed by opening of the furanylidene fragment of the latter and the formation of 2-(2-hetaryl)-6-hydroxy-3-(R-amino)-2-hexenenitriles.
• Reactions of 2-(2-hetaryl)-2-(tetrahydrofuran-2-ylidene)acetonitriles with tertiary amines
  作者：D. S. Milokhov、O. V. Khilya、A. V. Turov、R. I. Zubatyuk、G. V. Palamarchuk、O. V. Shishkin、A. A. Chekotilo、Yu. M. Volovenko

  DOI：10.1007/s10593-013-1207-3

  日期：2013.3

  The reactions of 2-(2-hetaryl)-2-(tetrahydrofuran-2-ylidene)acetonitriles with conformationally rigid and heterocyclic tertiary amines were investigated. Compounds with bipolar structures were obtained: 1-cyano-1-(2-hetaryl)-5-(pyridinium-1-yl)-1-penten-2-olates and 5-(4-aza-1-azoniobicyclo[2.2.2]oct-1-yl)-1-cyano-1-(2-hetaryl)pent-1-en-2-olates.