6-chloro-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxohexanenitrile | 1354518-61-8

• 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: 6-chloro-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxohexanenitrile
• CAS: 1354518-61-8
• 化学式: C₁₃H₁₂ClN₃O
• 分子量: 261.711
• InChiKey: GAGZHILADTWUNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-chloro-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxohexanenitrile 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以96%的产率得到(Z)-2-(benzimidazol-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitrile
  参考文献：
  名称：

  Synthesis of 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles

  摘要：

  The reaction of azolylacetonitriles with gamma-chlorobutyryl chlorides gave the corresponding 2-(1-R-1,3-dihydro-2H-benzimidazol-2-ylidene)-, 2-(1,3-benzothiazol-2-ylidene)-, and 6-chloro-2-(4-methylthiazol-2-ylidene)-3-oxohexanenitriles. A study of the intramolecular cyclization of 2-(quinazolin-2-ylidene)-3-oxo-6-hexanenitriles and -heptanenitriles has led to the development of an efficient method for the preparation of 2-(quinazolin-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitriles. The (Z,E)-isomerism of the synthesized 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles was studied.

  DOI：

  10.1007/s10593-011-0885-y
• 作为产物：
  描述：

  2-氰甲基苯并咪唑 、 4-氯丁酰氯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到6-chloro-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxohexanenitrile
  参考文献：
  名称：

  Synthesis of 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles

  摘要：

  The reaction of azolylacetonitriles with gamma-chlorobutyryl chlorides gave the corresponding 2-(1-R-1,3-dihydro-2H-benzimidazol-2-ylidene)-, 2-(1,3-benzothiazol-2-ylidene)-, and 6-chloro-2-(4-methylthiazol-2-ylidene)-3-oxohexanenitriles. A study of the intramolecular cyclization of 2-(quinazolin-2-ylidene)-3-oxo-6-hexanenitriles and -heptanenitriles has led to the development of an efficient method for the preparation of 2-(quinazolin-2-yl)-2-(tetrahydrofuran-2-ylidene)acetonitriles. The (Z,E)-isomerism of the synthesized 2-hetaryl-2-(tetrahydrofuran-2-ylidene)acetonitriles was studied.

  DOI：

  10.1007/s10593-011-0885-y

文献信息

• 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.