N-氨基甲酰-alpha-氨基-异丁酸 | 38605-63-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-氨基甲酰-alpha-氨基-异丁酸
• 中文别名: N-氨基甲酰-Α-氨基-异丁酸
• 英文名称: N-carbamoyl-α-aminoisobutyric acid
• 英文别名: N-carbamyl-α-aminoisobutyric acid；2-methyl-2-ureidopropionic acid；α-ureido-isobutyric acid；α-Ureido-isobuttersaeure；C.C-Dimethyl-hydantoinsaeure；N-carbamoyl-2-amino-2-methyl propionic acid；2-(Carbamoylamino)-2-methylpropanoic acid
• CAS: 38605-63-9
• 化学式: C₅H₁₀N₂O₃
• 分子量: 146.146
• InChiKey: FMXWPTBQTITILA-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.07 M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  N-氨基甲酰-alpha-氨基-异丁酸 在 盐酸 作用下， 生成 5,5-二甲基海因
  参考文献：
  名称：

  Kinetics of the acid-catalyzed closure of hydantoic acids. Effect of 2-aryl and 2-alkyl substituents

  摘要：

  DOI：

  10.1021/jo00948a017
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 barium dihydroxide 作用下， 生成 N-氨基甲酰-alpha-氨基-异丁酸
  参考文献：
  名称：

  Urech, Justus Liebigs Annalen der Chemie, 1872, vol. 164, p. 264

  摘要：

  DOI：

文献信息

• A largegem-dimethyl effect in the cyclization ofω-phenylhydantoic acids: computational modeling of thegem-dimethyl effect on the acid- or base-catalyzed cyclization of hydantoic acids and esters
  作者：P. M. Ivanov、I. G. Pojarlieff、I. B. Blagoeva、C. Jaime、V. T. Angelova、A. H. Koedjikov

  DOI：10.1002/poc.748

  日期：2004.5

  The rates of the cyclization of methyl-substituted 5-phenylhydantoic acids were measured in acid solutions. A particularly strong gem-dimethyl effect (GDME) was observed with the N-methyl compounds amounting to an acceleration of six powers of ten for the 2,2,3-trimethyl derivative. The variations in the free energies of activation for the cyclization of hydantoic acids and esters were modeled by the

  在酸溶液中测量甲基取代的5-苯基乙内酰脲酸的环化速率。观察到特别强的宝石-二甲基效应（GDME），其中N-甲基化合物对2,2,3-三甲基衍生物的加速度为十的六次幂。通过四面体中间体的应变能和由MM3力场计算的反应物的应变能，模拟了用于乙二酸和酯环化的活化自由能的变化。中性四面体中间体Ť 0是用于涉及酸催化和带负电荷的中间反应系列Ť -用于碱催化。对于完整系列的N-甲基取代的底物的酸催化环化，获得了与实验GDME的非常吻合的结果，显示出加速是由于反应物的应变增加所致。有T的结果-紧密平行，表明GDME的损失在碱催化下观察2,2,3- trimethylhydantoate酯不是由于在分子内应变Ť - 。线性相关性（斜率1.22，r 排除了重度偏离的母体酸的数据时，获得了针对5-苯基乙二酸的反应系列的自由能变化对应变能的曲线图（= 0.934）。在酯和酸的反应系列之间获得了优异的LFER。观察
• An efficient multi-component synthesis of N-1-alkylated 5-nitrouracils from α-amino acids
  作者：Jean-Guy Boiteau、Claire Bouix-Peter、Sandrine Chambon、Laurence Clary、Sebastien Daver、Laurence Dumais、Jean-François Fournier、Craig S. Harris、Kenny Mebrouk、Corinne Millois、Romain Pierre、Nicolas Rodeville、Sandrine Talano、Loïc Tomas

  DOI：10.1016/j.tetlet.2016.04.039

  日期：2016.6

  we show the limitations of this approach when quaternary C centres at N-1 became a key target for the programme. To access this key substructure, we developed an efficient multi-component reaction (MCR) from readily available α-amino acid precursors.

  的制备Ñ -1选择性烷基化尿嘧啶中间体通常要求选择性保护Ñ -3随后烷基化以Ñ -1和随后除去保护基团。在这封信中，我们展示了当N -1的四级C中心成为该计划的主要目标时这种方法的局限性。为了访问此关键子结构，我们从容易获得的α-氨基酸前体中开发了有效的多组分反应（MCR）。
• 4,5-Dihydroxyimidazolidin-2-ones in the α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 1. α-Ureidoalkylation of N-(carboxyalkyl)ureas
  作者：A. N. Kravchenko、K. A. Lyssenko、I. E. Chikunov、P. A. Belyakov、M. M. Il’in、V. V. Baranov、Yu. V. Nelyubina、V. A. Davankov、T. S. Pivina、N. N. Makhova、M. Yu. Antipin

  DOI：10.1007/s11172-010-0022-6

  日期：2009.2

  The α-ureidoalkylation of N-(carboxyalkyl)ureas (ureido acids) with 1,3-H2 s-, 1,3-Me 2 s-, and 1,3-Et2 s-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils were shown to decrease both in going from 1,3-H2 s- to 1,3-Me2 s- and 1,3-Et2 s- 4,5- dihydroxyimidazolidin-2-ones and with elongation and branching of the carboxyalkyl chain in the ureido acids under study. The optimal reaction time for most of ureido acids is 3 h. The reaction mechanism was proposed. This mechanism was partially confirmed by quantum chemical methods and 1H NMR spectroscopy. Crystals of a number of the newly synthesized compounds were studied by X-ray diffraction, and two new conglomerates were found. A method was developed for the enantiomeric analysis of some racemic N-(carboxyalkyl)-glycolurils by chiral-phase HPLC.

  系统研究了 N-(羧烷基)脲（脲酸）与 1,3-H2 s-、1,3-Me 2 s-和 1,3-Et2 s-4,5-二羟基咪唑烷-2-酮的α-脲烷基化反应。结果表明，从 1,3-H2 s- 到 1,3-Me2 s- 和 1,3-Et2 s- 4,5- 二羟基咪唑烷-2-酮，以及随着所研究的脲基酸中羧基烷基链的延长和分支，羟基甘油的产量都会降低。提出了反应机理。量子化学方法和 1H NMR 光谱法部分证实了这一机理。通过 X 射线衍射研究了一些新合成化合物的晶体，发现了两种新的同系物。通过手性相高效液相色谱法，建立了对一些外消旋 N-（羧基烷基）-甘氨酰脲对映体的分析方法。
• Process for producing optically active alpha-methylcysteine derivative
  申请人：Ohishi Takahiro

  公开号：US20060105435A1

  公开（公告）日：2006-05-18

  The present invention provides a simple industrial process for producing an L- or D-optically active α-methylcysteine derivative or its salt, which is a useful pharmaceutical intermediate, from readily available, inexpensive raw materials. In a process for producing an L- or D-optically active α-methylcysteine derivative or its salt, a racemic N-carbamoyl-α-methylcysteine derivative or its salt is D-selectively cyclized with hydantoinase to produce a D-5-methyl-5-thiomethylhydantoin derivative or its salt and an N-carbamoyl-α-methyl-L-cysteine derivative or its salt, which are then subjected to deprotection of the amino group and the sulfur atom, and hydrolysis.

  本发明提供了一种简单的工业过程，用于从易得、廉价的原材料中生产有用的药物中间体L-或D-光学活性α-甲基半胱氨酸衍生物或其盐。在生产L-或D-光学活性α-甲基半胱氨酸衍生物或其盐的过程中，利用咪唑烷酰肽酶选择性地对外消旋的N-氨基甲基半胱氨酸衍生物或其盐进行环化反应，生成D-5-甲基-5-硫甲基咪唑烷酮衍生物或其盐和N-氨基甲基-L-半胱氨酸衍生物或其盐，然后对氨基团和硫原子进行去保护作用，最后进行水解。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE ALPHA-METHYLCYSTEINE DERIVATIVE
  申请人：Ohishi Takahiro

  公开号：US20100197934A1

  公开（公告）日：2010-08-05

  The present invention provides a simple industrial process for producing an L- or D-optically active α-methylcysteine derivative or its salt, which is a useful pharmaceutical intermediate, from readily available, inexpensive raw materials. In a process for producing an L- or D-optically active α-methylcysteine derivative or its salt, a racemic N-carbamoyl-α-methylcysteine derivative or its salt is D-selectively cyclized with hydantoinase to produce a D-5-methyl-5-thiomethylhydantoin derivative or its salt and an N-carbamoyl-α-methyl-L-cysteine derivative or its salt, which are then subjected to deprotection of the amino group and the sulfur atom, and hydrolysis.

  本发明提供了一种简单的工业过程，用于从易得、廉价的原料中生产L-或D-光学活性α-甲基半胱氨酸衍生物或其盐，该衍生物是一种有用的药物中间体。在生产L-或D-光学活性α-甲基半胱氨酸衍生物或其盐的过程中，使用外消旋N-氨基甲基半胱氨酸衍生物或其盐与咪唑二酮酶D-选择性环化，以产生D-5-甲基-5-硫甲基咪唑二酮衍生物或其盐和N-氨基甲基-L-半胱氨酸衍生物或其盐，然后对氨基团和硫原子进行去保护作用，并进行水解。