5-hydroxy-1,3-dimethylimidazolidine-2,4-dione | 64732-10-1

• 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-hydroxy-1,3-dimethylimidazolidine-2,4-dione
• 英文别名: N,N'-dimethyl-5-hydroxyhydantoin；N,N-dimethyl-hydroxyhydantoin；5-hydroxyhydantoin；5-hydroxy-1,3-dimethyl-imidazolidine-2,4-dione；5-Hydroxy-1,3-dimethyl-imidazolidin-2,4-dion；5-hydroxy-1,3-dimethylhydantoin
• CAS: 64732-10-1
• 化学式: C₅H₈N₂O₃
• 分子量: 144.13
• InChiKey: AFUWTBVQIHBTMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-1,3-dimethylimidazolidine-2,4-dione 在 N-氯代丁二酰亚胺 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 7.17h， 生成 (±)-(R)-5-((R)-3-hydroxy-2-oxoindolin-3-yl)-1,3-dimethylimidazolidine-2,4-dione
  参考文献：
  名称：

  级联合成5-（吲哚-3-基）乙内酰脲的方法：在（±）-氧皂苷B的全合成中的应用

  摘要：

  通过在深共晶溶液（+）-酒石酸-二甲基脲中吲哚与乙醛酸/丙酮酸的反应，已经开发出一种5-（吲哚-3-基）乙内酰脲骨架合成的级联方法。来自深共晶溶液的N，N'-二甲基脲起反应物以及溶剂混合物的作用。中间体5-羟基乙内酰脲的分离及其与吲哚的反应为该反应提供了机械证据。该方法已成功应用于生物碱（±）-氧代皂苷B的首次全合成，总收率为48％。

  DOI：

  10.1021/acs.joc.0c02435
• 作为产物：
  描述：

  N,N'-dimethyl-5-hydroxy-5-benzylhydantoin 以 异丙醇 为溶剂， 反应 3.0h， 以23%的产率得到5-hydroxy-1,3-dimethylimidazolidine-2,4-dione
  参考文献：
  名称：

  Sato, Eisuke; Kanaoka, Yuichi, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 7, p. 3006 - 3008

  摘要：

  DOI：

文献信息

• Multicomponent Approach to Hydantoins and Thiohydantoins Involving a Deep Eutectic Solvent
  作者：Sambasivarao Kotha、Naveen K. Gupta、Vikas R. Aswar

  DOI：10.1002/asia.201900744

  日期：2019.9.16

  synthetic strategy to diverse hydantoins and thiohydantoins involving a three-component reaction with the aid of deep eutectic solvent. Here, N,N'-dimethyl urea and N,N'-dimethyl thiourea play a dual role as reactant and reaction medium along with l-(+)-tartaric acid. The three-component reaction provides an easy access to 5-amino-1,3-dialkyl-substituted hydantoins and thiohydantoins in good yields.

  我们报告了一种有效的合成策略，涉及多种乙内酰脲和巯基乙内酰脲，其中涉及在深共熔溶剂的帮助下进行三组分反应。在此，N，N′-二甲基脲和N，N′-二甲基硫脲与1-（+）-酒石酸一起起反应物和反应介质的双重作用。三组分反应提供了容易获得5-氨基-1,3-二烷基取代的乙内酰脲和巯基乙内酰脲的良好收率。
• Formation and Stability of New Hybrid Dichalcogena Dications(S-Se, S-Te and Se-Te) Bearing (2-Methylchalcogenomethyl)phenyl Skeleton
  作者：Hiroyuki Naka、Masayo Shindo、Tetsushi Maruyama、Soichi Sato、Naomichi Furukawa

  DOI：10.1246/cl.1999.723

  日期：1999.8

  Ethyl 2-(methylthiomethyl)phenyl selenide 1a, telluride 1b and ethyl 2-(methylselanylmethyl)phenyl telluride 1c were prepared and treated with 1 equivalent of triflic anhydride (Tf2O) or 2 equivalents of nitrosonium salts (NOBF4 or NOPF6) at low temperature to generate the corresponding selenathia, tellurathia and telluraselena dications(2a, 2b and 2c), the structures of which were determined by NMR spectroscopy and 2b was successfully isolated.

  制备了乙基 2-(甲硫基甲基)苯基硒化物 1a、碲化物 1b 和乙基 2-(甲硫基甲基)苯基碲化物 1c，并在低温下用 1 个等量的三酸酐（Tf2O）或 2 个等量的硝基锍盐（NOBF4 或 NOPF6）处理，生成相应的硒化物、通过核磁共振光谱测定了它们的结构，并成功地分离出了 2b。
• Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1
  作者：Sylvie Cortial、Philippe Chaignon、Didier Sergent、Sophie Dezard、Jamal Ouazzani

  DOI：10.1016/j.molcatb.2011.11.014

  日期：2012.4

  Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 mu M). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced Flavin Fl-(Red) and resembles those catalyzed by dihydropyrimidine clehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-(OOH) for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds. (C) 2011 Elsevier B.V. All rights reserved.
• �ber ein Reductionsproduct des Cholestrophans, den Dimethylglyoxylharnstoff
  作者：Rudolf Andreasch

  DOI：10.1007/bf01516818

  日期：1882.12
• Biltz; Heidrich, Chemische Berichte, 1921, vol. 54, p. 1830
  作者：Biltz、Heidrich

  DOI：——

  日期：——