1,3-dibenzyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile | 243836-01-3

• 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: 1,3-dibenzyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile
• 英文别名: (1,3-Dibenzyl-2,3-dihydro-1H-benzimidazol-2-yl)acetonitrile；2-(1,3-dibenzyl-2H-benzimidazol-2-yl)acetonitrile
• CAS: 243836-01-3
• 化学式: C₂₃H₂₁N₃
• 分子量: 339.44
• InChiKey: QGUJIPADWNMGSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-Dibenzylbenzimidazolium perchlorate 在 重水 、 sodium hydride 作用下， 生成 1,3-dibenzyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile
  参考文献：
  名称：

  Stable carbenes. Synthesis and properties of benzimidazol-2-ylidenes

  摘要：

  A new stable crystalline carbene, 1,3-bis(1-adamantyl)benzin-ddazol-2-ylidene, was synthesized by decomposition of 1,3-bis(I-adamantyl)-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile on heating under reduced pressure. Heteroaromatic 1,3-R-2-disubstituted benzimidazol-2-ylidenes, both stable (R = 1-Ad) and generated in situ (R = Me, Bzl), as well as 1,3,4,5-tetraphenyliniidazol-2-ylidene (generated in situ), reacted with acetonitrile to give the corresponding insertion products, 1, 3 -disubstituted 2-cyanomethyl-2,3-dihidro-1H-(benz)imidazoles. The geometric parameters of 1,3-bis(1-adamantyl)benzimidazol-2-ylidene, determined by X-ray analysis, suggest its lower aromaticity as compared to imidazol-2-ylidenes and 1,2,4-triazol-5-ylidenes. The structures of 2-cyanomethyl-2,3-dihydro-1H-benzimidazoles, 2-cyanomethyl-1,3,4,5-tetraphenyl-2,3-dihydro-1H-imidazole, and 1-(1-adamantyl)-5-cyanomethyl-3,4-diphenyl-4,5-dihydro-1H-1,2,4-triazole are characterized by partial conjugation in the heteroring; some compounds exhibit luminescence under UV irradiation. 1,3-Bis(1-adamantyl)benzimidazol-2-ylidene reacted with molecular sulfur in benzene to give 1,3-bis(1-adamantyl)-2,3-dihydro-1H-benzimidazole-2-thione, but it failed to react with selenium under analogous conditions.

  DOI：

  10.1134/s1070428006120116

文献信息

• Stable carbenes. Synthesis and properties of benzimidazol-2-ylidenes
  作者：N. I. Korotkikh、G. F. Raenko、T. M. Pekhtereva、O. P. Shvaika、A. H. Cowley、J. N. Jones

  DOI：10.1134/s1070428006120116

  日期：2006.12

  A new stable crystalline carbene, 1,3-bis(1-adamantyl)benzin-ddazol-2-ylidene, was synthesized by decomposition of 1,3-bis(I-adamantyl)-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile on heating under reduced pressure. Heteroaromatic 1,3-R-2-disubstituted benzimidazol-2-ylidenes, both stable (R = 1-Ad) and generated in situ (R = Me, Bzl), as well as 1,3,4,5-tetraphenyliniidazol-2-ylidene (generated in situ), reacted with acetonitrile to give the corresponding insertion products, 1, 3 -disubstituted 2-cyanomethyl-2,3-dihidro-1H-(benz)imidazoles. The geometric parameters of 1,3-bis(1-adamantyl)benzimidazol-2-ylidene, determined by X-ray analysis, suggest its lower aromaticity as compared to imidazol-2-ylidenes and 1,2,4-triazol-5-ylidenes. The structures of 2-cyanomethyl-2,3-dihydro-1H-benzimidazoles, 2-cyanomethyl-1,3,4,5-tetraphenyl-2,3-dihydro-1H-imidazole, and 1-(1-adamantyl)-5-cyanomethyl-3,4-diphenyl-4,5-dihydro-1H-1,2,4-triazole are characterized by partial conjugation in the heteroring; some compounds exhibit luminescence under UV irradiation. 1,3-Bis(1-adamantyl)benzimidazol-2-ylidene reacted with molecular sulfur in benzene to give 1,3-bis(1-adamantyl)-2,3-dihydro-1H-benzimidazole-2-thione, but it failed to react with selenium under analogous conditions.