1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile

• 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-dimethyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile
• 英文别名: 2-cyanomethyl-1,3-dimethyl-2H-benzimidazoline；1,3-Dimethyl-2,3-dihydro-1h-benzimidazol-2-yl-acetonitrile；2-(1,3-dimethyl-2H-benzimidazol-2-yl)acetonitrile
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: NNOOLEXJLNLGTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(triphenylphosphine)nickel(II) chloride 、 1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile 以 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到bis(1,3-dimethylbenzimidazol-2-ylidene)nickel(II) dichloride
  参考文献：
  名称：

  镍，钯和铜（I）的杂环卡宾络合物可作为有效的催化剂，用于还原酮*

  摘要：

  镍，钯和铜的碳络合物（I）在氢氧化钾存在下，在2-丙醇的影响下有效催化芳族酮的还原。双（1,3-二甲基苯并咪唑-2-亚烷基）碘化铜（I）和冠-双碳烯与碘化铜（I）的聚合络合物显示出最高的催化效率。

  DOI：

  10.1007/s10593-012-0947-9
• 作为产物：
  描述：

  Tetramethyltetraazafulvalene 、 乙腈 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile
  参考文献：
  名称：

  富电子烯烃与质子活性化合物的反应

  摘要：

  摘要：由富电子烯烃双(1,3-二甲基苯并咪唑烷-2-ylidene), I 或双(3-甲基苯并噻唑烷-2-ylidene), II 与质子活性化合物如亚磷酸二甲酯、二乙基亚磷酸酯、乙腈和苯甲醛分别得到2-取代苯并咪唑或苯并噻唑衍生物。合成的化合物通过1H、13C、31P-NMR、质谱、FT-IR光谱技术和微量分析进行鉴定。

  DOI：

  10.1080/00397919708005451

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.
• Heterocyclic carbene complexes of nickel, palladium, and copper(I) as effective catalysts for the reduction of ketones*
  作者：N. I. Korotkikh、V. Sh. Saberov、A. V. Kiselev、N. V. Glinyanaya、K. A. Marichev、T. M. Pekhtereva、G. V. Dudarenko、N. A. Bumagin、O. P. Shvaika

  DOI：10.1007/s10593-012-0947-9

  日期：2012.3

  Carbene complexes of nickel, palladium, and copper(I) effectively catalyze the reduction of aromatic ketones under the influence of 2-propanol in the presence of potassium hydroxide. Bis(1,3-dimethylbenzimidazol-2-ylidene)copper(I) iodide and the polymeric complex of crown-biscarbene with copper(I) iodide show the highest catalytic efficiency.

  镍，钯和铜的碳络合物（I）在氢氧化钾存在下，在2-丙醇的影响下有效催化芳族酮的还原。双（1,3-二甲基苯并咪唑-2-亚烷基）碘化铜（I）和冠-双碳烯与碘化铜（I）的聚合络合物显示出最高的催化效率。
• Reactions of Electron-Rich Olefins with Proton-Active Compounds
  作者：Hasan Küçükbay、Engin Çetinkaya、Bekir Çetinkaya、Michael F. Lappert

  DOI：10.1080/00397919708005451

  日期：1997.12

  Abstract: From the reaction of electron-rich olefins, bis(1,3-dimethylbenzimidazolidine-2-ylidene), I, or bis(3-methylbenzothiazolidine-2-ylidene), II with proton active compounds, such as dimethyl phosphite, diethyl phosphite, acetonitrile and benzaldehyde were obtained 2-substituted benzimidazole or benzothiazole derivatives. The compounds synthesized were identified by 1H, 13 C, 31P-NMR, mass, FT-IR

  摘要：由富电子烯烃双(1,3-二甲基苯并咪唑烷-2-ylidene), I 或双(3-甲基苯并噻唑烷-2-ylidene), II 与质子活性化合物如亚磷酸二甲酯、二乙基亚磷酸酯、乙腈和苯甲醛分别得到2-取代苯并咪唑或苯并噻唑衍生物。合成的化合物通过1H、13C、31P-NMR、质谱、FT-IR光谱技术和微量分析进行鉴定。