(R)-5-methyl-5-phenylhydantoin | 101693-73-6

• 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: (R)-5-methyl-5-phenylhydantoin
• 英文别名: (-)-(5R)-5-methyl-5-phenylhydantoin；(5R)-5-methyl-5-phenylimidazolidine-2,4-dione
• CAS: 101693-73-6
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD20727962
• 分子量: 190.202
• InChiKey: JNGWGQUYLVSFND-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 (R)-5-methyl-5-phenylhydantoin 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 37.0h， 以91%的产率得到(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylpropanoic acid
  参考文献：
  名称：

  Backbone modifications in peptidic inhibitors of flaviviral proteases

  摘要：

  The NS2B-NS3 protease is a promising target for the development of drugs against dengue virus (DENV), West Nile virus (WNV) and related flaviviruses. We report the systematic variation of the peptide backbone of the two lead compounds Bz-Arg-Lys-D-Phg-NH2 and Bz-Arg-Lys-D-Phg(OBn)-NH2. While inhibitory activity against WNV protease was generally decreased, the inhibitory potency against DENV protease could be conserved and increased in several peptidomimetics, particularly in those containing a (NMe)arginine fragment or an N-terminal alpha-keto amide. Methylation at the alpha-position of the C-terminal phenylglycine led to a 6-fold higher potency against DENV protease. Peptidomimetics with modified backbone showed increased resistance against hydrolytic attack by trypsin and alpha-chymotrypsin.

  DOI：

  10.1016/j.bmcl.2019.05.054
• 作为产物：
  描述：

  5-甲基-5-苯基乙内酰脲 以 异丙醚 、 水 、 丙酮 为溶剂， 反应 8.0h， 生成 (R)-5-methyl-5-phenylhydantoin
  参考文献：
  名称：

  脂肪酶催化的5,5-二取代乙内酰脲的拆分

  摘要：

  手性非外消旋5，5-二取代乙内酰脲是通过脂肪酶催化其N-酰氧基甲基的对映选择性水解或将其N-羟甲基酯化来制备的。

  DOI：

  10.1016/0957-4166(94)80097-9

文献信息

• Solution-phase synthesis and evaluation of tetraproline chiral stationary phases
  作者：Zhi Dai、Guozhong Ye、Charles U. Pittman、Tingyu Li

  DOI：10.1002/chir.22001

  日期：2012.4

  solution‐phase synthesis of multigram amounts of two 9‐fluorenylmethoxycarbonyl (Fmoc)‐protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution‐phase‐synthesized

  开发了一种协议方案，用于溶液相合成多克数量的两个9-芴基甲氧基羰基（Fmoc）保护的四脯氨酸肽。然后将这些四脯氨酸肽连接到氨基衍生的硅胶上。用三甲基乙酰基取代Fmoc基团会导致两个四脯氨酸手性固定相（CSP）。将这两种溶液相合成的四脯氨酸CSP与通过逐步固相合成制备的CSP的色谱行为进行比较，结果表明，这三种溶液均具有相似的色谱性能，可分离53种模型分析物。这表明寡聚脯氨酸的溶液相合成具有良好的批次重现性，选择器均质性以及可能的低成本等特定优势，是寡聚脯氨酸CSP固相合成的可行替代方法。手性，2012年。©2012 Wiley Periodicals，Inc.。
• Retention and Selectivity of Teicoplanin Stationary Phases after Copper Complexation and Isotopic Exchange
  作者：Alain Berthod、Alain Valleix、Veronique Tizon、Estelle Leonce、Celine Caussignac、Daniel W. Armstrong

  DOI：10.1021/ac010444t

  日期：2001.11.1

  Teicoplanin is a macrocyclic glycopeptide that is highly effective as a chiral selector for LC enantiomeric separations. Two possible interaction paths were investigated and related to solute retention and selectivity: (1) interactions with the only teicoplanin amine group and (2) role of hydrogen bonding interactions. Mobile phases containing 0.5 and 5 mM copper ions were used to try to block the

  Teicoplanin是一种大环糖肽，可作为LC对映体分离的高效手性选择剂。研究了两种可能的相互作用路径，它们与溶质保留和选择性有关：（1）与唯一的替考拉宁胺基的相互作用和（2）氢键相互作用的作用。含有0.5和5 mM铜离子的流动相被用来阻断胺基。发现在铜离子存在下，替考拉宁固定相分离大多数未衍生的外消旋氨基酸的能力降低。但是，它保持了分离非α-氨基酸对映体的能力。已经确定几乎没有铜-替考拉宁复合物形成。Cu2 +对某些α-氨基酸的对映体分离的作用似乎是由于这些溶质是良好​​的二齿配体，并在流动相中与铜离子形成络合物。使用乙腈-重水流动相与氘化氢进行同位素交换。发现在氘代流动相中，所有氨基酸的保留时间均较短。在氘代流动相中，没有胺基的极性或非极性分子的保留时间更长。在所有情况下，对映选择性因子均不受氘交换的影响。建议在氘化流动相中减少静电相互作用，并且氘化氧化物会使溶质可进入的固定相体积有
• Application of Cyclam-Capped β-Cyclodextrin-Bonded Silica Particles as a Chiral Stationary Phase in Capillary Electrochromatography for Enantiomeric Separations
  作者：Yinhan Gong、Hian Kee Lee

  DOI：10.1021/ac0204909

  日期：2003.3.1

  Two novel types of substituted cyclam-capped β-cyclodextrin (β-CD)-bonded silica particles have been prepared and used as chiral stationary phases in capillary electrochromatography (CEC). The two stationary phases have a chiral selector with three recognition sites:  β-CD, cyclam, and the latter's sidearm. They exhibit excellent enantioselectivities in CEC for a wide range of compounds as a result of the cooperative functioning of the anchored β-CD and cyclam. After inclusion of the metal ion (Ni2+) from the running buffer into the substituted cyclams and their sidearm ligands, the bonded stationary phases become positively charged and can provide extra electrostatic interactions with ionizable solutes and enhance the dipolar interactions with some polar neutral solutes. This enhances the host−guest interaction with some solutes and improves chiral recognition and enantioselectivity. These new types of stationary phases exhibit great potential for fast chiral separations in CEC.

  两种新型取代的环烷基顶端β-环糊精（β-CD）键合二氧化硅颗粒已被制备并用于毛细管电色谱（CEC）中的手性固定相。这两种固定相具有一个包含三个识别位点的手性选择剂：β-CD、环烷基和环烷基的侧链。它们在CEC中对广泛化合物表现出优异的对映选择性，原因在于锚定的β-CD和环烷基的协同作用。在运行缓冲液中金属离子（Ni2+）被包含到取代的环烷基及其侧链配体后，键合的固定相变为正电荷，从而能够与可电离溶质提供额外的静电相互作用，并增强与一些极性中性溶质的偶极相互作用。这增强了与某些溶质的宿主-客体相互作用，提高了手性识别和对映选择性。这些新型固定相在CEC中展现出快速手性分离的巨大潜力。
• Lipase-catalyzed resolution of 5,5-disubstituted hydantoins
  作者：Eisaku Mizuguchi、Kazuo Achiwa、Hideaki Wakamatsu、Yoshiyasu Terao

  DOI：10.1016/0957-4166(94)80097-9

  日期：1994.8

  Chiral non-racemic 5,5-disubstituted hydantoins were prepared by lipase-catalyzed enantioselective hydrolyses of their N-acyloxymethyl groups or esterification of their N-hydroxymethyl groups.

  手性非外消旋5，5-二取代乙内酰脲是通过脂肪酶催化其N-酰氧基甲基的对映选择性水解或将其N-羟甲基酯化来制备的。
• [EN] PROCESS FOR THE RESOLUTION OF ENANTIOMERS BY PREFERENTIAL EVAPORATIVE CRYSTALLIZATION<br/>[FR] PROCÉDÉ DE RÉSOLUTION D'ÉNANTIOMÈRES PAR CRISTALLISATION PAR ÉVAPORATION PRÉFÉRENTIELLE
  申请人：UNIV ROUEN

  公开号：WO2011073300A1

  公开（公告）日：2011-06-23

  The present invention relates to a process for the resolution of two enantiomers which consists in inducing the preferential crystallization of one enantiomer by adjusting the composition of a suspension or solution including a racemic mixture of the two enantiomers and a solvent, by evaporation of the latter.

  本发明涉及一种用于分离两个对映异构体的过程，该过程包括通过调整包括两个对映异构体的混合物和溶剂的悬浮液或溶液的组成，通过后者的蒸发来诱导一种对映异构体的优先结晶。