1-cyclohexylhydantoin | 6777-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-cyclohexylhydantoin
• 英文别名: 1-cyclohexyl-imidazolidine-2,4-dione；1-Cyclohexyl-imidazolidin-2,4-dion；1-Cyclohexylimidazolidine-2,4-dione
• CAS: 6777-06-6
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: QOYAISCZWRBCJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己基氨基乙腈盐酸盐 在 potassium cyanate 、 水 作用下， 生成 1-cyclohexylhydantoin
  参考文献：
  名称：

  NL6512700

  摘要：

  公开号：

文献信息

• An Efficient Approach for the Synthesis of N-1 Substituted Hydantoins
  作者：Vinod Kumar、M. P. Kaushik、Avik Mazumdar

  DOI：10.1002/ejoc.200701025

  日期：2008.4

  An efficient three-step route for the synthesis of N-1 alkyl/aryl-substituted hydantoins was developed from inexpensive commercially available substrates. The reaction of amines with cyanogen bromide takes place to give monoalkyl/aryl cyanamides. This on treatment with methyl bromoacetate in the presence of sodium hydride in tetrahydrofuran affords methyl N-cyano-N-alkyl/arylaminoacetate, which undergoes

  一种有效的三步法合成 N-1 烷基/芳基取代的乙内酰脲是从廉价的市售底物开发出来的。胺与溴化氰反应生成单烷基/芳基氰胺。在四氢呋喃中，在氢化钠存在下用溴乙酸甲酯处理得到 N-氰基-N-烷基/芳基氨基乙酸甲酯，在 50% H2SO4 存在下进行水解和环化，得到 N-1 取代的乙内酰脲。 - 优良的产量。通过该方法成功合成了在 N-1 位具有伯、仲、叔和芳基取代基的多种最终产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Highly efficient dialkylphosphate-mediated syntheses of hydantoins and a bicyclohydantoin under solvent-free conditions
  作者：Vinod Kumar、Hemlata Rana、Ravish Sankolli、M.P. Kaushik

  DOI：10.1016/j.tetlet.2011.09.029

  日期：2011.11

  were employed as the mild reagent to hydrolyze and cyclize the substrate in one step to give quantitative yields of the desired products. Syntheses of multivalent hydantoins viz bis-hydantoin, bicyclohydantoin have potentially widened the scope and applicability of the present method. Solvent-free conditions and very easy work-up procedure make the reaction convenient and eco-friendly. Single crystal

  已经通过新策略从基于氰酰胺的前体，即N-氰基-N-烷基/芳基氨基乙酸甲酯合成了不同取代的乙内酰脲。磷酸二烷基酯用作温和的试剂，可在一个步骤中水解和环化底物，以定量获得所需产物。多价乙内酰脲即双乙内酰脲，双环乙内酰脲的合成潜在地扩大了本方法的范围和适用性。无溶剂条件和非常简单的后处理程序使反应变得方便且环保。还报道了一些代表性化合物的单晶结构。
• Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils
  作者：A. N. Kravchenko、A. S. Sigachev、E. Yu. Maksareva、G. A. Gazieva、N. S. Trunova、B. V. Lozhkin、T. S. Pivina、M. M. Il’in、K. A. Lyssenko、Yu. V. Nelyubina、V. A. Davankov、O. V. Lebedev、N. N. Makhova、V. A. Tartakovsky

  DOI：10.1007/s11172-005-0307-3

  日期：2005.3

  Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, N′ N″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.

  在 4,5-二羟基咪唑烷-2-酮或乙二醛分别与一或两摩尔烷基脲在酸催化下发生反应的基础上，开发了合成手性 N-单烷基、N, N′-二烷基、N, N′-三烷基和 N, N′,N″,N′″-四烷基乙二醛的两种一般程序。N-单烷基和 N，N′-二烷基脲与乙二醛的反应具有区域选择性。量子化学计算和实验数据提出并部分证实了这些反应的机理。首次利用手性相高效液相色谱法分离了一些手性羟基乙醛的对映体。
• Pharmaceutical composition containing a hydantoin derivative and use of said derivative
  申请人：NIPPON ZOKI PHARMACEUTICAL CO., LTD.

  公开号：EP0780125A2

  公开（公告）日：1997-06-25

  The present invention is directed to a pharmaceutical composition comprising a hydantoin derivative represented by the following formula (I) or a pharmaceutically acceptable salt thereof wherein each of R1 and R2, which may be the same or different, represents hydrogen, an alkyl group or a cycloalkyl group; and each of X and Y, which may be the same or different, represents hydrogen, hydroxyl group, an alkyl group or an alkoxy group, or X and Y together represent an oxo group, and a pharmaceutically acceptable carrier or diluent. The above mentioned hydantoin derivative has an action of eliminating the active oxygen and the free radicals. Accordingly, it is useful for preparing a pharmaceutical agent for treating a variety of diseases in which active oxygen and free radicals are participated such as myocardial infarction, reperfusion disturbance, autoimmune diseases, fibrosis, pulmonary diseases, dermatological diseases, arthropathy, side effects of anticancer agents, radiation diseases, septic shock, inflammatory diseases and cataract.

  本发明涉及一种药物组合物，该药物组合物包含下式（I）所代表的 hydantoin 衍生物或其药学上可接受的盐 其中R1和R2（可以相同或不同）各自代表氢、烷基或环烷基；X和Y（可以相同或不同）各自代表氢、羟基、烷基或烷氧基，或X和Y共同代表氧代基团，以及药学上可接受的载体或稀释剂。 上述海因衍生物具有消除活性氧和自由基的作用。因此，它可用于制备治疗各种参与活性氧和自由基的疾病的药剂，如心肌梗塞、再灌注障碍、自身免疫性疾病、纤维化、肺部疾病、皮肤病、关节病、抗癌剂副作用、放射病、脓毒性休克、炎症性疾病和白内障。
• Therapeutic agent for intractable vasculitis
  申请人：NIPPON ZOKI PHARMACEUTICAL CO., LTD.

  公开号：EP1018339A1

  公开（公告）日：2000-07-12

  The invention provides a therapeutic agent for intractable vasculitis containing a hydantoin derivative represented by the formula (I) or a pharmaceutically acceptable salt thereof as an effective ingredient: wherein R1 and R2, which may be the same or different, represent hydrogen, an alkyl group or a cycloalkyl group; and each of X and Y, which may be the same or different, represent hydrogen, a hydroxyl group, an alkyl group or an alkoxy group, or X and Y together represent an oxo group. These compounds significantly suppress the generation of arthritis and arteritis (cutaneous ulcer and auricular infarcted necrosis) which were naturally developed in model animals (MRL/lpr), and further significantly elongat the survival rate of MRL/lpr mice. Consequently, the compound of the invention having low toxicity and less side effects is very useful as a highly safe therapeutic agent for intractable vasculitis such as malignant rheumatoid arthritis.

  本发明提供了一种治疗难治性脉管炎的药物，其有效成分含有由式（I）代表的海因衍生物或其药学上可接受的盐： 其中R1和R2可以相同或不同，分别代表氢、烷基或环烷基；X和Y可以相同或不同，分别代表氢、羟基、烷基或烷氧基，或X和Y共同代表氧代基团。 这些化合物能明显抑制模型动物（MRL/lpr）自然产生的关节炎和动脉炎（皮肤溃疡和耳廓梗塞坏死），并进一步明显延长 MRL/lpr 小鼠的存活率。因此，本发明的化合物毒性低、副作用小，是一种非常有用的治疗顽固性血管炎（如恶性类风湿性关节炎）的高安全性药物。