5,5-bis(4-methylphenyl)imidazolidine-2,4-dione | 50373-76-7

• 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: 5,5-bis(4-methylphenyl)imidazolidine-2,4-dione
• 英文别名: 5,5-di(4-methylphenyl)imidazolidine-2,4-dione；5,5-di-p-tolylimidazolidine-2,4-dione；5,5-bis(4-methylphenyl)hydantoin；5,5-di-p-tolyl-imidazolidine-2,4-dione；5,5-Di-p-tolyl-imidazolidin-2,4-dion；5,5-di(4-tolyl)hydantoin；2,4-Imidazolidinedione, 5,5-bis(4-methylphenyl)-
• CAS: 50373-76-7
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: DAERXVGJQHMIKV-UHFFFAOYSA-N

物化性质

• 熔点：
  295-299 °C(Solv: ethanol (64-17-5))
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-bis(4-methylphenyl)imidazolidine-2,4-dione 在 盐酸 、 铂 作用下， 生成 5,5-bis-(4-methyl-cyclohexyl)-imidazolidine-2,4-dione
  参考文献：
  名称：

  Researches on Substituted 5-Phenylhydantoins¹

  摘要：

  DOI：

  10.1021/ja01645a029
• 作为产物：
  描述：

  4,4'-二甲基联苯甲酰 在 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5,5-bis(4-methylphenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  3-Alkyl-(5,5′-diphenyl)imidazolidinediones as new cannabinoid receptor ligands

  摘要：

  Twenty-four 3-alkyl-(5,5'-diphenyl)imidazolidinediones were synthesized and evaluated as new cannabinoid receptor ligands. Three compounds exhibited a Ki value around 100 nM against [H-3]-SR 141716A binding obtained from human CB1 transfected CHO cells membranes. The lack of change of affinity in the presence of a non hydrolyzable GTP analogue seems to indicate they are cannabinoid antagonists. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00353-4

文献信息

• Magnetic magnetite nanoparticals catalyzed selective oxidation of α-hydroxy ketones with air and one-pot synthesis of benzilic acid and phenytoin derivatives
  作者：Xiaona Li、Dandan Xia、Zhiyong Wen、Bowen Gong、Maolin Sun、Yue Wu、Jie Zhang、Jun Sun、Yang Wu、Kai Bao、Weige Zhang

  DOI：10.1016/j.mcat.2018.05.013

  日期：2018.7

  A clean and efficient protocol for selective oxidation of α-hydroxy ketones using magnetic magnetite nanoparticals (Fe3O4·MNPs) as catalyst with air as green oxidant has been developed. Application of Fe3O4·MNPs was also proved to be successful in one-pot synthesis of benzilic acid and phenytoin derivatives. The facile one-pot procedure enhanced the production efficiency, shortened the reaction time

  已开发出一种清洁有效的方案，以磁性磁铁矿纳米粒子（Fe 3 O 4 ·MNPs）为催化剂，以空气为绿色氧化剂，选择性氧化α-羟基酮。Fe 3 O 4 ·MNPs在单锅合成苯甲酸和苯妥英衍生物中也被证明是成功的。简便的一锅法提高了生产效率，缩短了反应时间，并最大程度地减少了化学废物。值得注意的是，该催化剂可以重复使用至少五次，而没有任何明显的活性损失。
• An improved procedure for the synthesis of 4,4-disubstituted-3-oxo-1,2,5-thiadiazolidine 1,1 -dioxides
  作者：Zejun Xiao、Jack W. Timberlake

  DOI：10.1002/jhet.5570370418

  日期：2000.7

  An improved synthesis for the preparation of 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides has been developed. This facile two-step procedure fromα-amino acid esters and chlorosulfonyl isocyanate results in excellent yields of products.

  已经开发了用于制备3-氧代-1,2,5-噻二唑烷1，1-二氧化物的改进的合成方法。由α-氨基酸酯和氯磺酰基异氰酸酯组成的这种简便的两步过程可实现极好的产品收率。
• Hydantoin analogs inhibit the fully assembled ClpXP protease without affecting the individual peptidase and chaperone domains
  作者：Christian Fetzer、Vadim S. Korotkov、Stephan A. Sieber

  DOI：10.1039/c9ob01339c

  日期：——

  Proteolysis mediated by ClpXP is a crucial cellular process linked to bacterial pathogenesis. The development of specific inhibitors has largely focused on ClpP. However, this focus was challenged by a recent finding showing that conformational control by ClpX leads to a rejection of ClpP binders. Thus, we here follow up on a hit molecule from a high throughput screen performed against the whole ClpXP complex

  ClpXP介导的蛋白水解是与细菌发病机理相关的关键细胞过程。特异性抑制剂的开发主要集中在ClpP上。但是，最近的发现表明ClpX的构象控制导致ClpP结合蛋白被排斥，这一挑战受到了挑战。因此，我们在此跟踪了针对整个ClpXP复合物的高通量筛选中的命中分子，并证明了高效稳定的抑制作用是可能的。进一步的研究表明，该小分子与ClpP结合而不影响其活性。同样，该分子不抑制ClpX，并且在结合后保留ClpXP的整体寡聚状态。结构活性关系研究证实了该分子所有三个部分的结构限制，表明结合到一个确定的立体特异性口袋中。
• Therapeutic method of treating cardiac arrhythmias utilizing
  申请人：Miles Laboratories, Inc.

  公开号：US04006232A1

  公开（公告）日：1977-02-01

  3-substituted-5,5-diphenylhydantoin derivatives in which the 5,5-diphenylhydantoin moiety is attached at C.sub.3 by a loweralkylene bridge to a 4-phenyl-1-piperidyl, 4-hydroxy-4-phenyl-1-piperidyl, 4-phenyl-1,2,3,6-tetrahydropyridyl, 4-phenyl-1-piperazinyl, or loweralkylamino group are useful in the treatment of cardiac arrhythmias in mammals. One or both of the 5,5-diphenyl substituents optionally can be substituted in the ortho-, meta-, or para-positions with halogeno, lowerakyl, loweralkoxy, amino or nitro groups.

  3-取代-5,5-二苯基海达嗪衍生物，其中5,5-二苯基海达嗪基团通过较低的烷基桥连接到C.sub.3处，形成4-苯基-1-哌啶基、4-羟基-4-苯基-1-哌啶基、4-苯基-1,2,3,6-四氢吡啶基、4-苯基-1-哌嗪基或较低的烷基氨基团，在哺乳动物心律失常的治疗中是有用的。其中一个或两个5,5-二苯基取代基可以选择性地在邻位、间位或对位与卤素、较低烷基、较低烷氧基、氨基或硝基团进行取代。
• Synthesis and dynamic NMR studies of novel hydantoin and thiohydantoin derivatives. Crystal structure of diethyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl) fumarate and diethyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1<i>H</i>-imidazol-1-yl)fumarate
  作者：Mohammad M. Ghanbari、Marzieh Jamali、Gyula Batta、Attila C. Bényei

  DOI：10.3184/174751917x14932244903881

  日期：2017.5

  dialkyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate, 7. Single crystal X-ray diffraction study on 4b and 7b proved the structures unambiguously with C=O and SH functionality at the 2-position of the imidazole ring, respectively. Dynamic effects were observed in the NMR spectra of these compounds and were attributed to restricted rotation around the carbon-nitrogen single bonds

  在乙内酰脲或硫代乙内酰脲的存在下，化学计量的二烷基乙炔二羧酸酯与三苯基膦的反应提供了稳定的结晶磷叶立德。这些化合物经历 PPh3 的平滑消除以产生二烷基 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl)fumarate、4 或二烷基 2-(4,4-diaryl-2-mercapto-5-oxo -4,5-dihydro-1H-imidazol-1-yl)fumarate, 7. 4b 和 7b 的单晶 X 射线衍射研究清楚地证明了在咪唑环的 2-位具有 C=O 和 SH 官能团的结构， 分别。在这些化合物的 NMR 光谱中观察到动态效应，这归因于围绕碳 - 氮单键的受限旋转。旋转异构体的相互转化过程的旋转能垒 (ΔG#) 等于 (53.6 和 17.2) ± 2 kcal mol-1。