N-(2-咪唑啉-2-基)苯胺 | 1848-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-咪唑啉-2-基)苯胺
• 英文名称: N-phenyl-N-(4,5-dihydro-1H-imidazol-2-yl)amine
• 英文别名: 2-Anilino-imidazolin；2-Phenylamino-2-imidazolin；St 465；Imidazolidine, 2-(phenylimino)-；N-phenyl-4,5-dihydro-1H-imidazol-2-amine
• CAS: 1848-75-5
• 化学式: C₉H₁₁N₃
• 分子量: 161.206
• InChiKey: JCOPITWIWLFFPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.4
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  N-(2-咪唑啉-2-基)苯胺 、 苯丙炔酸甲酯 生成 7,8-diphenyl-2,8-dihydro-3H-imidazo[1,2-a]pyrimidin-5-one
  参考文献：
  名称：

  HAERTER H. P.; LICHTL H.; STAUSS U.; SCHINDLER O., HELV. CHIM. ACTA , 1976, 59, NO 4, 1203-1212

  摘要：

  DOI：
• 作为产物：
  描述：

  可乐定 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以100%的产率得到N-(2-咪唑啉-2-基)苯胺
  参考文献：
  名称：

  Pd/C–Et3N-mediated catalytic hydrodechlorination of aromatic chlorides under mild conditions

  摘要：

  A mild and efficient one-pot procedure for the hydrodechlorination of aromatic chlorides using a Pd/C-Et3N system was developed. A variety of aromatic chlorides could be dechlorinated at room temperature and under ambient hydrogen pressure. Et3N activates the catalysis and is likely to work as a single electron donor in this system. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.025

文献信息

• Process for synthesizing heterocyclic compounds
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US20040242560A1

  公开（公告）日：2004-12-02

  The invention provides the process illustrated in scheme 1 for synthesizing heterocyclic compounds of formula I. 1 In the process, an isothiocyanate of formula II is initially reacted with a primary amine of formula III to give a thiourea of formula IV. Subsequently, the thiourea of formula IV is converted to the corresponding heterocycle of formula I using a base and a sulfonyl chloride.

  该发明提供了合成式I的杂环化合物的方案1所示的过程。 在该过程中，首先将式II的异硫氰酸酯与式III的初级胺发生反应，得到式IV的硫脲。随后，利用一种碱和磺酰氯将式IV的硫脲转化为相应的式I的杂环化合物。
• Efficient Synthesis of 2-Arylamino-2-imidazolines and 2-Ami- nobenzimidazoles with Aminoiminomethanesulfonic Acid Derivatives
  作者：Farajollah Mohanazadeh、Navabe Nami、Samine Sadat Hosseini

  DOI：10.1002/cjoc.201190179

  日期：2011.5

  A highly efficient synthesis of 2‐arylamino‐2‐imidazolines and 2‐aminobenzimidazoles from aminoimino‐methanesulfonic acid derivatives is described. The method is simple and practical, generating imidazoline and benzimidazoline derivatives in excellent isolated yields.

  描述了从氨基亚氨基-甲磺酸衍生物高效合成2-芳基氨基-2-咪唑啉和2-氨基苯并咪唑。该方法简单实用，可以以优异的分离产率生成咪唑啉和苯并咪唑啉衍生物。
• Synthesis and carbonic anhydrase activating properties of a series of 2-amino-imidazolines structurally related to clonidine¹
  作者：Niccolò Chiaramonte、Soumia Maach、Caterina Biliotti、Andrea Angeli、Gianluca Bartolucci、Laura Braconi、Silvia Dei、Elisabetta Teodori、Claudiu T. Supuran、Maria Novella Romanelli

  DOI：10.1080/14756366.2020.1749602

  日期：2020.1.1

  for a long time. This compound has been extensively modified but only in few instances the imidazole ring has been replaced with other heterocycles. It was envisaged that the imidazoline ring could be a bioisoster of the imidazole moiety. Indeed, we report that clonidine, a 2-aminoimidazoline derivative, was found able to activate several human CA isoforms (hCA I, IV, VA, VII, IX, XII and XIII), with

  组胺的碳酸酐酶（CA，EC 4.2.1.1）活化特性早已为人所知。该化合物已被广泛修饰，但仅在少数情况下，咪唑环已被其他杂环取代。设想咪唑啉环可以是咪唑部分的生物等排体。确实，我们报道了可乐定是一种2-氨基咪唑啉衍生物，被发现能够激活几种人类CA亚型（hCA I，IV，VA，VII，IX，XII和XIII），其效力在微摩尔范围内，而无活性在hCA II上。然后合成了一系列与可乐定有关的2-氨基咪唑啉，并在选定的hCA亚型上进行了测试。这些化合物对hCA II无活性，同时在hCA I，VA，VII和XIII上显示出活化特性，KA值在微摩尔范围内。
• Efficient Synthesis of 2‐(<i>N</i>‐Substituted)‐2‐imidazolines and 2‐(<i>N</i>‐Substituted)‐1,4,5,6‐tetrahydropyrimidines
  作者：Wai Ming Kan、Shih‐Hsun Lin、Ching‐Yuh Chern

  DOI：10.1080/00397910500213005

  日期：2005.10.1

  Abstract A general method for the preparation of 2‐(N‐Substituted)‐2‐imidazolines and 2‐(N‐Substituted)‐1,4,5,6‐tetrahydropyrimidines is described. These heterocycles can be synthesized from their respective anilines with 2‐chloro‐2‐imidazoline or 2‐chloro‐1,4,5,6‐tetrahydropyrimidine, generated in situ from imidazolidin‐2‐one and tetrahydropyrimidin‐2(1H)‐one activated by dimethyl chlorophosphate

  摘要描述了制备 2-(N-取代)-2-咪唑啉和 2-(N-取代)-1,4,5,6-四氢嘧啶的一般方法。这些杂环可以由它们各自的苯胺与 2-氯-2-咪唑啉或 2-氯-1,4,5,6-四氢嘧啶合成，由咪唑啉-2-酮和四氢嘧啶-2(1H)-酮原位生成氯磷酸二甲酯活化，收率良好。
• Method for treating central nervous system disorders with substituted 2-imidazoline derivatives
  申请人：Hoener Marius

  公开号：US20070197569A1

  公开（公告）日：2007-08-23

  The present invention relates to a method for treating depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders which comprises administering to an individual a therapeutically effective amount of a compound of formula I wherein R, X, A, and n are as defined in the specification and pharmaceutically active salts, racemic mixtures, enantiomers, optical isomers and tautomeric forms thereof.

  本发明涉及一种治疗抑郁症、焦虑障碍、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、如精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用和代谢性疾病，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍、心血管疾病的方法，包括向个体施用化合物I的治疗有效量，其中R、X、A和n如规范中所定义，以及其药用活性盐、外消旋混合物、对映体、光学异构体和互变异构体形式。

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