N-(3-hydroxypropyl)urea | 16517-53-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-(3-hydroxypropyl)urea
• 英文别名: (3-Hydroxypropyl)urea；3-hydroxypropylurea
• CAS: 16517-53-6
• 化学式: C₄H₁₀N₂O₂
• mdl: MFCD01676014
• 分子量: 118.136
• InChiKey: DNPHEDNKXRMPAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxypropyl)urea 、 乙二醛三聚物二水合物 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  1-取代的半硫甘醇糖醇的合成与结构

  摘要：

  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。

  DOI：

  10.1055/s-0040-1707391
• 作为产物：
  描述：

  N-benzyl-N'-(3-hydroxy-propyl)-urea 在 钯 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 N-(3-hydroxypropyl)urea
  参考文献：
  名称：

  A simple conversion of amines into monosubstituted ureas in organic and aqueous solvents

  摘要：

  A versatile and highly efficient synthesis of monosubstituted ureas is described. The reaction of an amine with 4-nitrophenyl-N-benzylcarbamate, followed by hydrogenolysis, provides the corresponding urea in high yield and purity. This carbamate can also be employed for the derivatization of water-soluble polyamines (e.g. aminoglycoside antibiotics), while other reagents (e.g, benzylisocyanate) fail to give the desired products in any significant yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02289-9

文献信息

• 4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxy-, N-hydroxy-, and N-aminoalkylureas 2. α-Ureidoalkylation of N-(hydroxyalkyl)ureas
  作者：A. N. Kravchenko、A. S. Sigachev、P. A. Belyakov、M. M. Ilyin、K. A. Lyssenko、V. A. Davankov、O. V. Lebedev、N. N. Makhova、V. A. Tartakovsky

  DOI：10.1007/s11172-009-0165-5

  日期：2009.6

  The α-ureidoalkylation of N-(hydroxyalkyl)ureas (ureido alcohols) with 1,3-H2- and 1,3-Me2-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils decrease both in going from 1,3-H2- to 1,3-Me2-4,5-dihydroxyimidazolidin-2-one and with increasing length (or with branching) of the hydroxyalkyl chain in ureido alcohols. The optimal reaction time for ureido alcohols is 1 h. The X-ray diffraction study showed that 2-(2-hydroxy-1,1-dimethylethyl)glycoluril crystallizes as a conglomerate. The enantiomeric analysis of 2-(2-hydroxyethyl)glycoluril was carried out by chiral-phase HPLC.

  系统研究了 N-（羟基烷基）脲（脲醇）与 1,3-H2- 和 1,3-Me2-4,5- 二羟基咪唑烷-2-酮的 α-ureido 烷基化反应。从 1,3-H2- 到 1,3-Me2-4,5-二羟基咪唑烷-2-酮的过程中，以及随着脲基乙醇中羟基烷基链长度（或分支）的增加，糖醛酸的产量都会降低。X 射线衍射研究表明，2-(2-羟基-1,1-二甲基乙基)甘氨酰脲结晶为团聚体。采用手性相高效液相色谱法对 2-(2-羟乙基)甘氨酰脲进行了对映体分析。
• 4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxyalkyl-, N-hydroxyalkyl-, and N-aminoalkylureas 5. Synthesis of N-hydroxyalkyl-1,5-diphenylglycolurils
  作者：G. A. Gazieva、V. V. Baranov、A. N. Kravchenko

  DOI：10.1007/s11172-010-0236-7

  日期：2010.6

  A systematic investigation of α-ureidoalkylation of N-hydroxyalkylureas with 4,5-dihydroxy-1,3-dimethyl-4,5-diphenylimidazolidin-2-one allowed the discovery of a synthetic route to earlier unknown N-hydroxyalkyl-1,5-diphenylglycolurils. The yields of these compounds decrease with lengthening and branching of the alkyl chain in the starting ureas.

  通过对 N-羟基烷基脲与 4,5-二羟基-1,3-二甲基-4,5-二苯基咪唑烷-2-酮进行α-脲基烷基化的系统研究，发现了一条合成早先未知的 N-羟基烷基-1,5-二苯基甘氨酰脲的路线。这些化合物的产量随着起始脲中烷基链的延长和分支而降低。
• Direct Synthesis of 1-Alkyl-6-hydroxyalkyl-3a,6a-diphenylglycolurils from 1-Alkylimidazolinones and Their Cyclic Analogues
  作者：Vladimir Baranov、Maria Antonova、Natalya Kolotyrkina、Igor Zanin、Angelina Kravchenko

  DOI：10.1055/s-0037-1611937

  日期：2019.2

  result of a study of novel cyclocondensations of 1-alkylureas with tetrahydroimidazooxazolones, tetrahydroimidazooxazinones and 1-(hydroxyalkyl)ureas with 1-substituted imidazolinones. A mechanism to rationalize the highly regioselective formation of the target glycolurils is proposed.

  作为对 1-烷基脲与四氢咪唑并恶唑酮、四氢咪唑并恶嗪酮和 1-（羟烷基）的新型环缩合的研究的结果，开发了两种直接合成以前无法获得的 1-烷基-6-（羟烷基）-3a,6a-二苯基甘脲的方法含有 1-取代咪唑啉酮的尿素。提出了一种使目标甘脲的高度区域选择性形成合理化的机制。
• α-Thioureidoalkylation of functionally substituted ureas: II. Synthesis of thio analogs of N-hydroxyalkyl-1,5-diphenylglycolurils
  作者：G. A. Gazieva、V. V. Baranov、A. N. Kravchenko、N. N. Makhova

  DOI：10.1134/s1070428011100216

  日期：2011.10

  Reactions of N-(hydroxyalkyl)ureas with 4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones gave previously unknown 4,6-dialkyl-1-hydroxyalkyl-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-2-ones which may be regarded as thio analogs of N-(hydroxyalkyl)glycolurils.
• Regioselective synthesis of 2,8-disubstituted 1,5-diphenylglycolurils
  作者：Vladimir V. Baranov、Maria M. Antonova、Yulia V. Nelyubina、Natal’ya G. Kolotyrkina、Igor E. Zanin、Angelina N. Kravchenko、Nina N. Makhova

  DOI：10.1016/j.mencom.2014.04.017

  日期：2014.5

  A new synthetic approach to 2,8-disubstituted 1,5-diphenylglycolurils is based on condensation of 1-(hydroxyalkyl)ureas (ureido alcohols) with tetrahydroimidazooxazolone and tetrahydroimidazooxazinone derivatives which were unexpectedly obtained by acid-catalyzed reaction of ureido alcohols with benzil. An X-ray diffraction study of the supramolecular organization of the obtained compounds revealed the chirality of the crystals of achiral glycoluril molecules.