4,5-二羟基-1-甲基咪唑烷-2-酮 | 22322-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 4,5-二羟基-1-甲基咪唑烷-2-酮
• 英文名称: mono-N-methyl-4,5-dihydroxyimidazolidin-2-one
• 英文别名: 4,5-Dihydroxy-1-methylimidazolidin-2-one
• CAS: 22322-62-9
• 化学式: C₄H₈N₂O₃
• 分子量: 132.119
• InChiKey: FCCYTEWKVKVUEB-UHFFFAOYSA-N

物化性质

• 沸点：
  430.6±45.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium thiocyanide 、 4,5-二羟基-1-甲基咪唑烷-2-酮 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以1.07 g的产率得到1-methyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one
  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：

  草酸醛 、 N-甲基脲 以 水 为溶剂， 生成 4,5-二羟基-1-甲基咪唑烷-2-酮
  参考文献：
  名称：

  Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils

  摘要：

  在 4,5-二羟基咪唑烷-2-酮或乙二醛分别与一或两摩尔烷基脲在酸催化下发生反应的基础上，开发了合成手性 N-单烷基、N, N′-二烷基、N, N′-三烷基和 N, N′,N″,N′″-四烷基乙二醛的两种一般程序。N-单烷基和 N，N′-二烷基脲与乙二醛的反应具有区域选择性。量子化学计算和实验数据提出并部分证实了这些反应的机理。首次利用手性相高效液相色谱法分离了一些手性羟基乙醛的对映体。

  DOI：

  10.1007/s11172-005-0307-3

文献信息

• α-Ureidoalkylation of thiosemicarbazide and aminoguanidine
  作者：A. S. Sigachev、A. N. Kravchenko、P. A. Belyakov、O. V. Lebedev、N. N. Makhova

  DOI：10.1007/s11172-006-0344-6

  日期：2006.5

  azo[4,5-e][1,2,4]triazin-6-ones, 4,5-bis(3-thiosemicarbazido(guanidinoamino))imidazolidin-2-ones, and 1,3-dialkyl-4-(guanidinoimino)imidazolidin-2-ones by α-ureidoalkylation of thiosemicarbazide or aminoguanidine were found. A novel conglomerate in the series of imidazolidin-2-one derivatives was detected: 4,5-bis(guanidinoamino)-1,3-dimethylimid-azolidin-2-one dihydrochloride dihydrate.

  通过硫代氨基脲或氨基胍的 α-ureido 烷基化作用，发现了偶氮[4,5-e][1,2,4]三嗪-6-酮、4,5-双（3-硫代氨基脲（胍基氨基））咪唑烷-2-酮和 1,3-二烷基-4-（胍基氨基）咪唑烷-2-酮。在咪唑烷-2-酮衍生物系列中发现了一种新的集合体：4,5-双（胍基氨基）-1,3-二甲基咪唑烷-2-酮二盐酸盐二水合物。
• Reactions of sulfonamides with 4,5-dihydroxyimidazolidin-2-ones
  作者：G. A. Gazieva、A. N. Kravchenko、O. V. Lebedev、Yu. A. Strelenko、K. Yu. Chegaev

  DOI：10.1007/bf02495610

  日期：1998.8

  The interaction of sulfonamides with 4,5-dihydroxyimidazolidin-2-ones was studied for the first time. The earlier unknown 4,4'-sulfonyldiiminobis(1,3-dialkylimidazolidin-2-ones) and 4(S)-aryl(alkyl)-sulfonyliminoimidazolidin-2-ones were synthesized. A probable pathway of the reaction was proposed. 1,3-Diethyl-4,5-dihydroxyimidazolidin-2-one was isolated and described.
• Enthalpies and heat capacities of solution of racemic N-methyl-substituted glycolurils in water at T=(278.15 to 313.15)K
  作者：Evgeniy V. Ivanov、Dmitriy V. Batov

  DOI：10.1016/j.tca.2015.09.023

  日期：2015.11

  The molar enthalpies of solution of racemic (with enantiomer ratio of 1:1) 2-monomethyl-, 2,6-dimethyl-, and 2,4,6-trimethylglycolurils (2-MMGU, 2,6-DMGU and 2,4,6-TMGU, respectively) in water were measured calorimetrically in the temperature range between (278.15 and 313.15)K and at p=99.6 kPa. Derived from experimental data, the standard (at infinite dilution) molar enthalpic characteristics of the dissolution process are positive by sign and increase with rising temperature as well as in a sequence of 2,4,6-TMGU < 2,6-DMGU < 2-MMGU. In the same way, the standard heat capacity of solution decreases distinctly, leading to the conclusion that the effect of hydrophobic hydration is more pronounced for the more N-methylated solute. It was suggested that, despite the presence of hydrophobic moieties (N-sited methyl groups) in the molecules considered, a hydrophilic constituent (via H-bonding) seems to be the predominant one in the total enthalpy effect of a solute hydration. (C) 2015 Elsevier B.V. All rights reserved.