4-chloro-N'-(4-chlorophenyl)benzenecarboximidamide | 138240-23-0

• 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: 4-chloro-N'-(4-chlorophenyl)benzenecarboximidamide
• CAS: 138240-23-0
• 化学式: C₁₃H₁₀Cl₂N₂
• 分子量: 265.142
• InChiKey: HASRBBLHBNEQIE-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C(Solv: chloroform (67-66-3))
• 沸点：
  355.6±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-chloro-N'-(4-chlorophenyl)benzenecarboximidamide 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 异丙醇 、 甲苯 为溶剂， 生成 1,2-bis-(4-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles

  摘要：

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.

  DOI：

  10.1021/jm049120y
• 作为产物：
  描述：

  对氯苯甲腈 、 对氯苯胺 在 三甲基铝 作用下， 以 甲苯 为溶剂， 以87%的产率得到4-chloro-N'-(4-chlorophenyl)benzenecarboximidamide
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships at the GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at the Recombinant Human GABA_A Receptor of a Series of Substituted 1,2-Diphenylimidazoles

  摘要：

  A series of new 1,2-diphenylimidazole derivatives (la-x) were synthesized and evaluated for their ability to potentiate gamma-aminobutyric acid (GABA)-evoked currents in Xenopus laevis oocytes expressing recombinant human GABAA receptors. Many of these compounds enhanced GABA action with potencies (EC50 = 0.19-19,mu M) and efficacies (maximal efficacies of up to 640%) similar to or greater than those of anesthetics such as etomidate, propofol, and alphaxalone. Structure- activity relationship analysis revealed that the presence of an ester moiety in the imidazole ring was required for full agonist properties, while modifications made in the phenyl rings affected potency and efficacy, with ethyl 2-(4-bromophenyl)-l-(2,4-dichlorophenyl)-1H4-imidazolecarboxylate showing the highest potency. These compounds potentiated the [H-3]GABA binding to rat brain membranes, suggesting a site of interaction different from that of GABA. As for etomidate, mutation of asparagine-265 in the beta 2 subunit of the GABA(A) receptor into serine reduced the ability of derivative 1i to modulate the GABA function.

  DOI：

  10.1021/jm049120y

文献信息

• Samarium(II) iodide induced reductive coupling of nitriles with nitro compounds
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1039/a803077d

  日期：——

  The intermolecular and intramolecular reductive coupling of a cyano group with a nitro group induced by SmI2 was studied. Amidines and 2-aminoquinoline derivatives are prepared in good yields under neutral and mild conditions respectively.

  利用SmI2诱导的氰基与硝基的分子间及分子内还原偶联反应被研究。在中性和温和条件下，分别以良好产率制备了脒和2-氨基喹啉衍生物。
• Facile Synthesis of Amidines via the Intermolecular Reductive Coupling of Nitriles with Nitro Compounds Induced by Samarium(ii) Iodide
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1039/a803011a

  日期：——

  The intermolecular reductive coupling of nitriles with nitro compounds induced by SmI2 was studied; amidine derivatives are prepared in good yields under neutral and mild conditions.

  由 SmI2 诱导的腈与硝基化合物的分子间还原偶联反应被研究；在中性和温和条件下，生成的脒类衍生物产率较高。
• Low-Valent Titanium Induced Reductive Coupling of Nitriles with Nitro Compounds
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1080/00397919808004430

  日期：1998.9

  Abstract The intermolecular and intramolecular reductive coupling of a cyano group with a nitro group induced by a low-valent titanium reagent prepared from TiCl4/Sm was studied. Amidines and 2-aminoquinolines derivatives are preparied in good yields under mild conditions respectively.

  摘要 研究了由TiCl4/Sm 制备的低价钛试剂诱导氰基与硝基的分子间和分子内还原偶联。脒和 2-氨基喹啉衍生物分别在温和条件下以良好的收率制备。
• Reactions of Aryliminodimagnesium with Some<i>N</i>,<i>N</i>-Dimethylcarboxamides and Benzonitriles Affording Various Types of Amidines. Correction of Previous Results on Formamidine Formation from<i>N</i>,<i>N</i>-Dimethylformamide
  作者：Masao Okubo、Mikio Tanaka、Yuri Murata、Nobuyuki Tsurusaki、Yasumasa Omote、Yukinobu Ikubo、Koji Matsuo

  DOI：10.1246/cl.1991.1965

  日期：1991.11

  Some symmetrical and unsymmetrical form- and benzamidines were prepared by the reaction of ArN(MgBr)2 with Ar’CN, HCONMe2 and related compounds in tetrahydrofurn.

  通过在四氢呋喃中将ArN(MgBr)2与Ar’CN、HCONMe2及相关化合物反应制备了一些对称和非对称的形式和苯胺。
• DABCO-Promoted [3+2] Annulation for Efficient Synthesis of 1,2,5-Triaryl-1H-imidazoles from Substituted β-Nitrostyrenes and N-Arylbenzimidamides
  作者：Cunde Wang、Yue Zhang、Xinyi Wan、Jianbo Gan

  DOI：10.1055/a-1533-6872

  日期：2021.12

  An efficient approach to the synthesis of 1,2,5-trisubstituted imidazole derivatives was investigated via a DABCO-promoted formal [3+2]-annulation reaction of substituted N-arylbenzimidamides and substituted β-nitrostyrenes. The annulation reaction is implemented easily to afford the corresponding products in moderate to good yields with excellent regioselectivity.

  通过 DABCO 促进的取代 N-芳基苯甲酰胺和取代 β-硝基苯乙烯的正式 [3+2]-环化反应，研究了一种合成 1,2,5-三取代咪唑衍生物的有效方法。环化反应很容易实现，以中等至良好的收率和优异的区域选择性提供相应的产物。