4-脲基丁酸 | 2609-10-1

• 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: 4-脲基丁酸
• 中文别名: 丁酸-4-脲
• 英文名称: grateloupine
• 英文别名: γ-Ureido-buttersaeure；4-ureidobutyric acid；4-ureidobutanoic acid；4-Ureido-butyric acid；4-(carbamoylamino)butanoic acid
• CAS: 2609-10-1
• 化学式: C₅H₁₀N₂O₃
• mdl: MFCD01811285
• 分子量: 146.146
• InChiKey: QYTWIMMLQKHPGL-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C
• 沸点：
  344.6±34.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  4-脲基丁酸 在 三氯氧磷 作用下， 反应 6.0h， 以38%的产率得到多鳞番荔枝酮
  参考文献：
  名称：

  Synthese von 2,4-Dioxohexahydro-1,3-diazepinen

  摘要：

  DOI：

  10.1055/s-1982-30030
• 作为产物：
  描述：

  1,3-di-(γ-carboxypropyl)urea 在 potassium nitrite 、 硫酸 、 氨 、 水 作用下， 生成 4-脲基丁酸
  参考文献：
  名称：

  Amino Acids. V. 1,3-Di-(ι-carboxyalkyl)-thioureas and Their Chemistry

  摘要：

  DOI：

  10.1021/ja01539a058
• 作为试剂：
  描述：

  1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one 在 盐酸 、 4-脲基丁酸 作用下， 以 水 、 异丙醇 为溶剂， 生成 1,3-二甲基脲 、 联苯甲酰
  参考文献：
  名称：

  Specific features of the reaction of vanadyl acetylacetonate with tert-butyl hydroperoxide

  摘要：

  Reaction of vanadyl acetylacetonate with tert-butyl hydroperoxide (benzene, 20 degrees C) at any molar ratio leads to the elimination of ligand and its oxidation mainly to CO2 and acetic acid. At the (acac)(2)VO: t-BuOOH ratio above 1: 10 liberation of oxygen partially in the singlet state takes place.

  DOI：

  10.1134/s1070363209080143

文献信息

• Protecting Group Free Synthesis of Carboxyl-substituted Dihydropyrimidines Through Biginelli Reaction
  作者：Eugeniy N. Ostapchuk、Andrey S. Plaskon、Oleksandr O. Grygorenko、Andrey A. Tolmachev、Sergey V. Ryabukhin

  DOI：10.1002/jhet.1568

  日期：2013.11

  acetoacetic acid derivatives, and various carboxyl‐containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono‐substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one‐pot, protecting group free synthesis of dihydropyrimidines

  探索了氯三甲基硅烷促进的苯甲醛，乙酰乙酸衍生物和各种含羧基尿素的Biginelli型反应。发现脲取代基的空间负荷强烈影响反应结果。特别是，该方法仅在带有脂肪族或芳香族基团的直链单取代尿素中有效。该方法可以进行具有保护功能的二氢嘧啶的单锅，无保护基的合成。
• Synthesis and Structure of 1-Substituted Semithioglycolurils
  作者：Vladimir V. Baranov、Anton A. Galochkin、Yulia V. Nelyubina、Angelina N. Kravchenko、Nina N. Makhova

  DOI：10.1055/s-0040-1707391

  日期：2020.9

  Two methods for the synthesis of previously unavailable 1-substituted semithioglycolurils were developed. These methods consist of the cyclocondensation of 1-substituted ureas with 4,5-dihydroxy- or 4,5-dimethoxyimidazolidine-2-thione or glyoxal, followed by the reaction of the resulting 1-substituted 4,5-dihydroxyimidazolidine-2-ones with HSCN in a two-step one-pot procedure. Two of the desired semithioglycolurils

  开发了两种合成先前不可用的1-取代的半硫甘脲的方法。这些方法包括1-取代的脲与4，5-二羟基-或4，5-二甲氧基咪唑烷-2-硫酮或乙二醛的环缩合，然后使所得的1-取代的4，5-二羟基咪唑烷-2-酮反应。 HSCN采用两步一锅法。获得了两种期望的半硫代糖基尿嘧啶，为团块。
• Regioselective reactions of N-(carboxyalkyl)- and N-(aminoethyl)ureas with glyoxal and 1,2-dioxo-1,2-diphenylethane
  作者：A. N. Kravchenko、V. V. Baranov、G. A. Gazieva、I. E. Chikunov、Yu. V. Nelyubina

  DOI：10.1007/s11172-014-0446-5

  日期：2014.2

  Regioselective reactions of N-(carboxyalkyl)ureas (ureido acids) and N-(aminoethyl)ureas with 1,2-dioxo-1,2-diphenylethane (benzyl) and glyoxal are studied in detail. The structure of the reactants affects the reaction regioselectivity. Acid-catalyzed reactions of glyoxal with 1-[2-(dimethylamino(acetylamino))ethyl]ureas and benzene with ureido acids result mainly in 2,6-di-substituted glycolurils

  详细研究了 N-（羧基烷基）脲（脲基酸）和 N-（氨基乙基）脲与 1,2-二氧-1,2-二苯基乙烷（苄基）和乙二醛的区域选择性反应。反应物的结构影响反应的区域选择性。乙二醛与 1-[2-(二甲氨基(乙酰氨基))乙基]脲和苯与脲酸的酸催化反应主要产生 2,6-二取代甘脲。2,6-二（甲氧基羰基乙基）甘脲的结构通过 X 射线衍射明确确定。
• 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。
• EP3418276
  申请人：——

  公开号：——

  公开（公告）日：——