N-(2,3-dimethylphenyl)benzamidine | 108838-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,3-dimethylphenyl)benzamidine
• 英文别名: N-(2,3-dimethylphenyl)benzimidamide；N-(2,3-Dimethyl-phenyl)-benzamidin；N'-(2,3-dimethylphenyl)benzenecarboximidamide
• CAS: 108838-67-1
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: NXHJIHYKYHJQOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2,3-dimethylphenyl)benzamidine 在 N-氯代丁二酰亚胺 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 0.16h， 生成 4,5-dimethyl-2-phenyl-1H-benzimidazole
  参考文献：
  名称：

  N-Chlorosuccinimide/Sodium Hydroxide-Mediated Synthesis of Benzimidazoles from Amidines under Mild Conditions

  摘要：

  A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.

  DOI：

  10.3987/com-12-s(n)53
• 作为产物：
  描述：

  苯甲腈 、 2,3-二甲基苯胺 以 二甲基亚砜 为溶剂， 反应 17.0h， 以85%的产率得到N-(2,3-dimethylphenyl)benzamidine
  参考文献：
  名称：

  对苯醌和N-Arylamidines的非芳香化四氢苯并咪唑合成及其细胞毒性潜能

  摘要：

  用简单的方法由对苯醌和N芳基lam胺合成了新的四氢苯并咪唑，并评估了它们的细胞毒性潜力。其中，三种在µm范围内具有细胞毒性。

  DOI：

  10.1002/ejoc.201801077

文献信息

• 430. Cyclic amidines. Part VII. Preparation of benziminazoles from N′-aryl-N-hydroxyamidines
  作者：M. W. Partridge、H. A. Turner

  DOI：10.1039/jr9580002086

  日期：——
• Unaromatized Tetrahydrobenzimidazole Synthesis from <i>p</i> -Benzoquinone and <i>N</i> -Arylamidines and their Cytotoxic Potential
  作者：Minh Quan Tran、Thanh Binh Nguyen、Wamtinga Richard Sawadogo、Ludmila Ermolenko、Sungmi Song、Pascal Retailleau、Marc Diederich、Ali Al-Mourabit

  DOI：10.1002/ejoc.201801077

  日期：2018.11.15

  New tetrahydrobenzimidazoles were synthesized using a simple method from p‐benzoquinone and N‐arylamidines, and their cytotoxic potential was evaluated. Among them, three are cytotoxic in the µm range.

  用简单的方法由对苯醌和N芳基lam胺合成了新的四氢苯并咪唑，并评估了它们的细胞毒性潜力。其中，三种在µm范围内具有细胞毒性。
• N-Chlorosuccinimide/Sodium Hydroxide-Mediated Synthesis of Benzimidazoles from Amidines under Mild Conditions
  作者：Thanh Binh Nguyen、Ali Al-Mourabit、Ludmila Ermolenko

  DOI：10.3987/com-12-s(n)53

  日期：——

  A convenient room-temperature one-pot procedure for the preparation of benzimidazoles derivatives from N-arylamidines has been developed. The reaction of N-aryl-N'-chloro amidines, generated by the treatment of N-arylamidines with N-chlorosuccinimide, in presence of sodium hydroxide provides benzimidazoles in good to excellent yields. Nitrogen anion generated in situ from succinimide (by-product of the chlorination step using NCS) and hydroxide anion was found to be highly effective as Bronsted base to promote the cyclization into benzimidazole of N-aryl-N'-chloroamidine.