N-(4-chloro-phenyl)-benzimidoyl isothiocyanate | 20800-28-6

• 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-(4-chloro-phenyl)-benzimidoyl isothiocyanate
• 英文别名: N-(p-Chlorphenyl)-benzimidoyl-isothiocyanat；N-(4-chlorophenyl)benzenecarboximidoyl isothiocyanate
• CAS: 20800-28-6
• 化学式: C₁₄H₉ClN₂S
• 分子量: 272.758
• InChiKey: DKVPQXDAKLASSL-UHFFFAOYSA-N

物化性质

• 沸点：
  393.1±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-chloro-phenyl)-benzimidoyl isothiocyanate 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 N-{[(E)-4-Chloro-phenylimino]-phenyl-methyl}-pyrrolidine-1-carboximidothioic acid methyl ester
  参考文献：
  名称：

  Synthesis of Functionally Substituted 1,3-Diaza-1,3-butadienes

  摘要：

  报道了三种从易得的硫脲衍生物合成各种稳定的1,3-二氮-1,3-丁二烯的方法。

  DOI：

  10.1055/s-1990-26892
• 作为产物：
  描述：

  N-(4-氯-苯基)-苯酰胺 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 生成 N-(4-chloro-phenyl)-benzimidoyl isothiocyanate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors

  摘要：

  A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [H-3]CCPA to human A(1) adenosine receptors, whereas modest and varying effects were observed on the binding of [H-3]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A(2A) and A(3) receptors. Compounds 7a and 71 displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A(2A) receptors, whereas 7a showed some activity on A(3) receptors.

  DOI：

  10.1021/jm030863d

文献信息

• Synthesis and regioselective [4+2] cycloaddition/nucleophilic reactions of N-arylamino-1:3-diaza-1:3-butadienes with ketenes and accompanying rearrangements
  作者：Paramita D. Dey、Arun K. Sharma、Sachchida N. Rai、Mohinder P. Mahajan

  DOI：10.1016/0040-4020(95)00372-f

  日期：1995.7

  -butadienes 4 are shown to undergo regioselective reactions with phenyl- and chloroketenes resulting in high yields of 3-aryl-2-methylthio6-phenyl-4(3H)-pyrimidinones 7. Similar reactions with bromo- and iodoketenes, resulted, via aziridinium intermediates 12, in good yields of 3-aryl-S-(N-arylamino)-2-methylthio-6-phenyl4(3H)-pyrimidinones 13, The mechanistic aspects of cycloadditions and semi-empirical

  N-ArylAMino-1：3-diaza-1：3-butadienes 4与苯基和氯乙烯酮发生区域选择性反应，导致3-芳基-2-甲基硫代6-苯基-4（3H）-嘧啶酮7的高收率。经由叠氮鎓中间体12与溴和碘酮的类似反应，以高收率产生了3-芳基-S-（N-芳基氨基）-2-甲硫基-6-苯基4（3H）-嘧啶酮13，环加成反应的机理还报道了这些二氮杂丁二烯的​​半经验AM1计算结果。
• Goerdeler,J.; Weber,D., Chemische Berichte, 1968, vol. 101, # 10, p. 3475 - 3490
  作者：Goerdeler,J.、Weber,D.

  DOI：——

  日期：——