N,N'-bis-(2,4-dichloro-phenyl)-formamidine | 105625-12-5

• 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,N'-bis-(2,4-dichloro-phenyl)-formamidine
• 英文别名: N,N'-Bis-(2,4-dichlor-phenyl)-formamidin；N,N'-Bis(2,4-dichlorophenyl)methanimidamide；N,N'-bis(2,4-dichlorophenyl)methanimidamide
• CAS: 105625-12-5
• 化学式: C₁₃H₈Cl₄N₂
• 分子量: 334.032
• InChiKey: SRIBHSWMNXJOLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-bis-(2,4-dichloro-phenyl)-formamidine 在 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 以53%的产率得到6-chloro-1-(2,4-dichlorophenyl)-1H-benzimidazole
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of 2-Unsubstituted, N-Substituted Benzimidazoles

  摘要：

  An efficient copper-catalyzed intramolecular arylation of formamidines forming 2-unsubstituted benzimidazoles in excellent yields is reported. Sixteen examples bearing sterically demanding substituents on nitrogen like Mes, 2,6-diisopropylphenyl, or 2-tert-butylphenyl and tolerating various functional groups demonstrate the utility of this method.

  DOI：

  10.1021/jo902160y
• 作为产物：
  描述：

  2,4-二氯苯胺 、 原甲酸三乙酯 在 溶剂黄146 作用下， 以54%的产率得到N,N'-bis-(2,4-dichloro-phenyl)-formamidine
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of 2-Unsubstituted, N-Substituted Benzimidazoles

  摘要：

  An efficient copper-catalyzed intramolecular arylation of formamidines forming 2-unsubstituted benzimidazoles in excellent yields is reported. Sixteen examples bearing sterically demanding substituents on nitrogen like Mes, 2,6-diisopropylphenyl, or 2-tert-butylphenyl and tolerating various functional groups demonstrate the utility of this method.

  DOI：

  10.1021/jo902160y

文献信息

• Takahashi; Satake, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 135,137
  作者：Takahashi、Satake

  DOI：——

  日期：——
• The influence of remote substituent in tetrakis(μ-N,N′-diarylformamidinato)–dirhodium(II) compounds. Part 7. Linear free energy relationships in dinuclear compounds
  作者：Tong Ren、Chun Lin、Edward J. Valente、Jeffrey D. Zubkowski

  DOI：10.1016/s0020-1693(99)00317-5

  日期：2000.1

  Synthesis and characterizations are reported for the tetrakis(mu-N,N'-diarylformamidinato)dirhodium(II) compounds, where Ar is either XC6H4- with X as p-OMe (1), p-Me (2), H (3), m-OMe (4), p-Cl (5), m-Cl (6), m-CF3 (7), p-CF3 (8), or 3,4-Cl2C6H3 (9), or 3,5-Cl2C6H3 (10). The quasireversible redox couples Rh-2(6+)/Rh-2(5+) (A), Rh-2(5+)/Rh-2(4+) (B), and Rh-2(4+)/Rh-2(3+) (C) were observed for all the compounds with the exception of 9. The electrode potentials are related to the Hammett constant (sigma) of X by the following equation: Delta E-1/2 = E-1/2(X) - E-1/2(H) = rho(8 sigma) mV with the reactivity constant rho for the redox couples A, B, and C as 96, 98, and 97 mV, respectively. Molecular structures of compounds 4 and 10 were determined via X-ray diffraction studies. (C) 2000 Elsevier Science S.A. All rights reserved.
• Copper-Catalyzed Synthesis of 2-Unsubstituted, <i>N</i>-Substituted Benzimidazoles
  作者：Keiichi Hirano、Akkattu T. Biju、Frank Glorius

  DOI：10.1021/jo902160y

  日期：2009.12.18

  An efficient copper-catalyzed intramolecular arylation of formamidines forming 2-unsubstituted benzimidazoles in excellent yields is reported. Sixteen examples bearing sterically demanding substituents on nitrogen like Mes, 2,6-diisopropylphenyl, or 2-tert-butylphenyl and tolerating various functional groups demonstrate the utility of this method.