5-(1-methylpropyl)-2,4-imidazolidinedione | 40856-76-6

• 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: 5-(1-methylpropyl)-2,4-imidazolidinedione
• 英文别名: (S)-5-sec-butylimidazolidine-2,4-dione；(S)-5-((S)-sec-butyl)-imidazolidine-2,4-dione；(S)-5-((S)-sec-Butyl)-imidazolidin-2,4-dion；(5S)-5-[(2S)-butan-2-yl]imidazolidine-2,4-dione
• CAS: 40856-76-6
• 化学式: C₇H₁₂N₂O₂
• 分子量: 156.184
• InChiKey: ZUYPRBNQYTZYIK-WHFBIAKZSA-N

物化性质

• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2S,3S)-3-methyl-2-ureidopentanoic acid 在 盐酸 作用下， 生成 5-(1-methylpropyl)-2,4-imidazolidinedione
  参考文献：
  名称：

  Boyd, Biochemical Journal, 1933, vol. 27, p. 1838,1844

  摘要：

  DOI：

文献信息

• Dibutylphosphate (DBP) mediated synthesis of cyclic N,N′-disubstituted urea derivatives from amino esters: a comparative study
  作者：Sumit K. Agrawal、Manisha Sathe、A.K. Halve、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.08.083

  日期：2012.11

  The N,N′-disubstituted urea derivatives such as amino acid hydantoins and dihydrouracil derivatives were prepared starting from natural and unnatural amino acid esters using dibutylphosphate (DBP). During the attempted synthesis of N-heterocycles with larger than six-membered rings containing the N,N′-disubstituted urea functionalities, three unexpected products namely squamolone, N-methyl pyrrolidine-2-one

  的Ñ，Ñ '二取代的脲衍生物如氨基酸乙内酰脲和二氢尿嘧啶衍生物制备来自使用磷酸二丁酯（DBP）的天然和非天然氨基酸酯起始。在试图合成具有大于六元环的N-杂环的N-杂环的过程中，所述六元环包含N，N′-二取代的尿素官能团，分离了三种意想不到的产物，即扁豆酚酮，N-甲基吡咯烷-2-酮和二酮哌嗪。
• Mechanochemical Preparation of Hydantoins from Amino Esters: Application to the Synthesis of the Antiepileptic Drug Phenytoin
  作者：Laure Konnert、Benjamin Reneaud、Renata Marcia de Figueiredo、Jean-Marc Campagne、Frédéric Lamaty、Jean Martinez、Evelina Colacino

  DOI：10.1021/jo5017629

  日期：2014.11.7

  eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters

  描述了在行星式球磨机中由各种氨基酯盐酸盐和氰酸钾生态制备5-和5,5-二取代的乙内酰脲的环保方法。一锅/两步方案包括脲基酯中间体的形成，然后碱催化环化成乙内酰脲。这种易于操作的机械化学方法在光滑条件下应用于多种α-和β-氨基酯，可产生高产率的乙内酰脲，而无需纯化步骤。例如，该方法被应用于抗癫痫药苯妥英钠的“绿色”合成，而无需使用任何有害的有机溶剂。
• Synthesis of 1S,5R- and 1R,5S-glycoluriles by diastereospecific α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one
  作者：Il’ya E. Chikunov、Angelina N. Kravchenko、Pavel A. Belyakov、Konstantin A. Lyssenko、Vladimir V. Baranov、Oleg V. Lebedev、Nina N. Makhova

  DOI：10.1070/mc2004v014n06abeh002050

  日期：2004.1

  A diastereospecific method for the synthesis of individual enantiomers of 1S,5R- and 1R,5S-glycoluriles has been developed based on the α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one.

  基于（S）/（R）-N-氨基甲酰基-α-氨基酸与4,5的α-脲基烷基化反应，开发了一种非对映体特异性的方法，用于合成1S，5R-和1R，5S-糖醇的单个对映体-二羟基咪唑烷基-2-酮。
• Methods for producing diastereomers of isoleucine
  申请人：——

  公开号：US20040048342A1

  公开（公告）日：2004-03-11

  Methods for producing single diastereomers of isoleucine in high stereochemical purity are provided. D-isoleucine is produced by converting (R)-2-methylbutyraldehyde to a diastereomeric mixture of D-isoleucine hydantoin and L-allo-isoleucine hydantoin (5S-[(R)-1-methylpropyl]hydantoin) under conditions whereby no significant racemization of the chiral center in (R)-2-methylbutyraldehyde occurs, followed by contacting said diastereomeric hydantoin mixture with a D-hydantoinase to stereoselectively hydrolyze any D-isoleucine hydantoin in the mixture to the corresponding N-carbamoyl-D-isoleucine, preferably under conditions permitting the simultaneous epimerization of the chiral center at C-5 of the hydantoin. The simultaneous epimerization permits the reaction to be carried out to substantial completion so that the diastereomeric hydantoin mixture is converted to N-carbamoyl-D-isoleucine in high yield. The N-carbamoyl-D-isoleucine is then decarbamoylated to produce D-isoleucine. Similar procedures are used to produce single diastereomers of L-isoleucine, L-allo-isoleucine, and D-allo-isoleucine.

  提供了生产高立体化纯度的单对异构体异亮氨酸的方法。通过将(R)-2-甲基丁醛转化为D-异亮氨酸肼和L-异构异亮氨酸肼(5S-[(R)-1-甲基丙基]肼)的对映异构体混合物来生产D-异亮氨酸，条件下(R)-2-甲基丁醛手性中心没有发生显著的消旋化，然后将该对映异构体肼混合物与D-肼酶接触，以立体选择性水解混合物中的任何D-异亮氨酸肼为相应的N-氨基甲酰-D-异亮氨酸，最好在同时使肼环的C-5手性中心发生对映异构化的条件下进行。同时的对映异构化使反应可以进行到相当的完成度，以便将对映异构体肼混合物转化为高收率的N-氨基甲酰-D-异亮氨酸。然后将N-氨基甲酰-D-异亮氨酸脱氨甲酰化以产生D-异亮氨酸。类似的程序用于生产单对映异构体的L-异亮氨酸、L-异构异亮氨酸和D-异构异亮氨酸。
• US6830904B2
  申请人：——

  公开号：US6830904B2

  公开（公告）日：2004-12-14