trans-1,3-diethyl-4,5-dihydroxyimidazolidin-2-one

• 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: trans-1,3-diethyl-4,5-dihydroxyimidazolidin-2-one
• 英文别名: (4R,5R)-1,3-diethyl-4,5-dihydroxyimidazolidin-2-one
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: HAEJKWYMBFWXMQ-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-1,3-diethyl-4,5-dihydroxyimidazolidin-2-one 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.0h， 以75%的产率得到1,3-二乙基乙内酰脲
  参考文献：
  名称：

  3,3'-双（6,8-二烷基-2,4-二氧杂-6,8-二氮杂双环[3.3.0] octan-7-ones的首个代表化合物的合成

  摘要：

  3,3'-bi（2,4-dioxa-6,8-diazabicyclo [3.3.0] octan-7-ones）的第一个代表是通过乙二醛以2,2'-bi的形式合成的（4，5-二羟基-1，3-二氧杂戊环）与N，N′-二烷基脲。X射线分析支持了它们的结构。1,3-二烷基咪唑烷-2,4-二酮（乙内酰脲）已被分离为副产物，其形成机理已通过实验证实。

  DOI：

  10.1002/jhet.5570430523
• 作为产物：
  描述：

  草酸醛 、 1,3-二乙基脲 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 trans-1,3-diethyl-4,5-dihydroxyimidazolidin-2-one
  参考文献：
  名称：

  New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN

  摘要：

  A general and highly effective protocol for the direct synthesis of mono- and dithioglycolurils containing various substituents at the 1,3-nitrogen atoms has been developed based on the condensation of easily accessible dihydroxyimidazolidin-2-ones with HSCN under mild reactions conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.071

文献信息

• Diastereoselective synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and their structure
  作者：A. N. Kravchenko、V. V. Baranov、Yu. V. Nelyubina、G. A. Gazieva、I. V. Svitan’ko

  DOI：10.1007/s11172-012-0010-0

  日期：2012.1

  Studies on the synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) based on the condensation of ureas or thioureas with glyoxal or 1,2-dioxo-1,2-diphenylethane showed high diastereoselectivity in the formation of racemates (trans-diastereomers) of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and meso-forms (cis-diastereomers) of 4,5-dihydroxy-4,5-diphenyl-1,3-dialkylimidazolidine-2-thiones; plausible mechanisms of their formation were suggested. X-ray diffraction studies confirmed structures of diastereomers for separate examples of racemates and meso-forms of 4,5-dihydroxyimidazolidin-2-ones (-thiones).

  基于脲类或硫脲类与乙二醛或 1,2-二氧代-1.2-二苯基乙烷缩合合成 4,5-二羟基咪唑烷-2-酮（-thiones）的研究表明，4,5-二羟基咪唑烷-2-酮（-thiones）的外消旋体（反式-非对映异构体）的形成具有高度非对映选择性、2-二苯基乙烷缩合而成的 4,5-二羟基咪唑烷-2-酮（-硫酮）的外消旋体（反式-非对映异构体）和 4,5-二羟基-4,5-二苯基-1,3-二烷基咪唑烷-2-硫酮的中间体（顺式-非对映异构体）的非对映选择性很高；提出了它们的合理形成机制。X 射线衍射研究证实了 4,5-二羟基咪唑烷-2-酮（-硫酮）外消旋体和中消旋体的非对映异构体结构。
• Spontaneous resolution in the imidazolidin-2-one series
  作者：Angelina N. Kravchenko、Gul’nara K. Kadorkina、Andrey S. Sigachev、Elena Yu. Maksareva、Konstantin A. Lyssenko、Pavel A. Belyakov、Oleg V. Lebedev、Oleg N. Kharybin、Nina N. Makhova、Remir G. Kostyanovsky

  DOI：10.1070/mc2003v013n03abeh001736

  日期：2003.1

  For the first time, spontaneous resolution of trans-dihydroxyimidazolidin-2-one 1a was performed and racemisation of (-)-1a was studied; regiospecific reaction of 1a-c with aminoguanidine resulted in derivatives 2a-c; compound 2b was also shown to undergo spontaneous resolution, and the absolute configuration (4R,5R) of (-)-2b crystals was established by X-ray diffraction analysis.
• Synthesis of first representatives of 3,3′-bi(6,8-dialkyl-2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones)
  作者：Andrey S. Sigachev、Angelina N. Kravchenko、Galina A. Gazieva、Pavel A. Belyakov、Natal'Ya G. Kolotyrkina、Oleg V. Lebedev、Nina N. Makhova、Konstantin A. Lyssenko

  DOI：10.1002/jhet.5570430523

  日期：2006.9

  The first representatives of 3,3′-bi(2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones) have been synthesized by a reaction of glyoxal as form of 2,2′-bi(4,5-dihydroxy-1,3-dioxalane) with N,N′-dialkylureas. Their structures have been supported by X-ray analysis. 1,3-Dialkylimidazolidine-2,4-diones (hydantoins) have been isolated as by-products and their formation mechanism has been experimentally confirmed

  3,3'-bi（2,4-dioxa-6,8-diazabicyclo [3.3.0] octan-7-ones）的第一个代表是通过乙二醛以2,2'-bi的形式合成的（4，5-二羟基-1，3-二氧杂戊环）与N，N′-二烷基脲。X射线分析支持了它们的结构。1,3-二烷基咪唑烷-2,4-二酮（乙内酰脲）已被分离为副产物，其形成机理已通过实验证实。
• New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN
  作者：Vladimir V. Baranov、Yulia V. Nelyubina、Angelina N. Kravchenko、Natalya G. Kolotyrkina、Ksenia A. Biriukova

  DOI：10.1016/j.tetlet.2015.09.071

  日期：2015.10

  A general and highly effective protocol for the direct synthesis of mono- and dithioglycolurils containing various substituents at the 1,3-nitrogen atoms has been developed based on the condensation of easily accessible dihydroxyimidazolidin-2-ones with HSCN under mild reactions conditions. (C) 2015 Elsevier Ltd. All rights reserved.