2-benzylamino-4,5-dihydro-1H-imidazole | 38941-36-5

• 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: 2-benzylamino-4,5-dihydro-1H-imidazole
• 英文别名: 1H-Imidazol-2-amine, 4,5-dihydro-N-(phenylmethyl)-；N-benzyl-4,5-dihydro-1H-imidazol-2-amine
• CAS: 38941-36-5
• 化学式: C₁₀H₁₃N₃
• 分子量: 175.233
• InChiKey: SDROEWZZAHSJDT-UHFFFAOYSA-N

物化性质

• 沸点：
  303.5±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzylamino-4,5-dihydro-1H-imidazole 在 sodium dithionite 、 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.17h， 生成 7-amino-8-benzyl-6-formylamino-2,8-dihydro-3H-imidazo[1,2-a]pyrimidin-5-one
  参考文献：
  名称：

  Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones

  摘要：

  The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat.

  DOI：

  10.1021/jm00185a008
• 作为产物：
  描述：

  2-甲硫基-2-咪唑啉 、 苄胺 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以99%的产率得到2-benzylamino-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  温和条件下异硫脲碘化物和胺的鸟苷化合成五元和六元环胍

  摘要：

  摘要 通过异硫脲碘化物与等摩尔量的各种胺在四氢呋喃中反应，一步得到环状氢碘化胍。所得氢碘化物用氢氧化钠或阴离子交换树脂中和，以定量产率提供相应的取代环胍。图形概要

  DOI：

  10.1080/00397911.2016.1269927

文献信息

• 2-IMIDAZOLINES
  申请人：Galley Guido

  公开号：US20090018180A1

  公开（公告）日：2009-01-15

  The present invention relates to compounds of formula I wherein X—Y, R 1 , and n are as defined herein and to their pharmaceutically active salts. Compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1 and are useful for the treatment of 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.

  本发明涉及式I的化合物，其中X—Y、R1和n如本文所定义，并且涉及它们的药用活性盐。式I的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1，适用于治疗抑郁症、焦虑障碍、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力有关的障碍、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、物质滥用以及代谢性障碍，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、睡眠和昼夜节律障碍，以及心血管疾病。
• Heterocyclic compounds as P2X7 ion channel blockers
  申请人：Shum Patrick

  公开号：US20050026916A1

  公开（公告）日：2005-02-03

  The present invention relates to a novel series of 4,5-diphenyl-2-amino-4,5-dihydro-imidazole derivatives of the formula II: wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , X and Y are as defined herein. This invention also relates to methods of making these compounds. The compounds of this invention are P2X7 ion channel blockers and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases having an inflammatory component, including inflammatory bowel disease, rheumatoid arthritis and disease conditions associated with the central nervous system, such as stroke, Alzheimer's disease, etc.

  本发明涉及一种新的4,5-二苯基-2-氨基-4,5-二氢咪唑衍生物系列，其化学式为II： 其中R、R1、R2、R3、R4、R5、X和Y如本文所定义。本发明还涉及制备这些化合物的方法。本发明的化合物是P2X7离子通道阻断剂，因此在作为药用剂方面具有用途，特别是在治疗和/或预防具有炎症成分的各种疾病方面，包括炎症性肠病、类风湿关节炎以及与中枢神经系统相关的疾病状况，如中风、阿尔茨海默病等。
• C-N bond forming reactions in the synthesis of substituted 2-aminoimidazole derivatives
  作者：Asier Gómez-SanJuan、José Manuel Botija、Almudena Méndez、Nuria Sotomayor、Esther Lete

  DOI：10.3998/ark.5550190.p008.058

  日期：——

  Carbon-nitrogen bond forming reactions oriented to the synthesis of 2-amino-imidazolidines and imidazoles have been investigated. The C-2 amination of imidazolidinones, via the corresponding 2-chlorodihydroimidazoles, led to 2-benzylaminodihydroimidazole or bis(dihydroimidazole)amino derivatives by choosing the adequate experimental conditions. On the other hand, the use of N-acyl-2-methylsulfanyldihydroimidazoles

  已经研究了以合成 2-氨基-咪唑烷和咪唑为导向的碳-氮键形成反应。通过选择适当的实验条件，咪唑啉酮的 C-2 胺化，通过相应的 2-氯二氢咪唑，产生 2-苄氨基二氢咪唑或双（二氢咪唑）氨基衍生物。另一方面，N-酰基-2-甲基硫基二氢咪唑的使用允许与芳香胺，例如对茴香胺进行反应。最后，钯催化的 BuchwaldHartwig 胺化是 2-卤代咪唑和芳香胺在相应咪唑合成中 CN 偶联的首选方法。
• Tetrahydropyrimidines
  申请人：Janssen Pharmaceutica

  公开号：US03963718A1

  公开（公告）日：1976-06-15

  Compounds of the class of imidazo[1,2-a]-imidazoles, imidazo[1,2-a]pyrimidines and pyrimido-[1,2-a]pyrimidines useful as central nervous system (CNS) antidepressants; and certain novel precursors therefor.

  属于咪唑并[1,2-a]-咪唑、咪唑[1,2-a]嘧啶和嘧啶并[1,2-a]嘧啶类化合物，可用作中枢神经系统（CNS）抗抑郁药物；以及某些新颖的前体。
• Facile Guanidine Formation under Mild Acidic Conditions
  作者：Kosuke Namba、Kohei Takeuchi、Atsushi Nakayama、Keiji Tanino

  DOI：10.1055/s-0035-1562478

  日期：——

  method for converting isothioureas into guanidines was developed. The use of amine salts of bis(trifluoromethanesulfonyl)imide as a nitrogen source was found to induce an efficient conversion under weak acidic conditions at 50 °C. The conversion was applicable to the various amines and carbamate-protected thioureas, and various carbamate-protected cyclic guanidines were obtained in high yields. In particular

  开发了一种将异硫脲转化为胍的有效方法。发现使用双（三氟甲磺酰基）酰亚胺的胺盐作为氮源可在 50 °C 的弱酸性条件下诱导有效转化。该转化适用于各种胺类和氨基甲酸酯保护的硫脲，高产率得到各种氨基甲酸酯保护的环胍。特别是，双（三氟甲磺酰基）亚胺铵盐是一种有用的 N1 源，用于构建单保护的环胍。