1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one | 66242-64-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one
• 英文别名: 1,3-dimethyl-4,5-diphenyl-4,5-dihydroxyimidazolidin-2-one；4,5-dihydroxy-1,3-dimethyl-4,5-diphenylimidazolidin-2-one；DHI；4,5-dihydroxy-1,3-dimethyl-4,5-diphenyl-imidazolidin-2-one；4,5-Dihydroxy-1,3-dimethyl-4,5-diphenyl-imidazolidin-2-on；1.3-Dimethyl-4.5-dioxy-4.5-diphenyl-imidazolidon-(2)
• CAS: 66242-64-6
• 化学式: C₁₇H₁₈N₂O₃
• mdl: MFCD00184211
• 分子量: 298.342
• InChiKey: NXQPKFDLVDLKBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C (decomp)
• 沸点：
  480.0±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one 生成 1,3-二甲基-5,5-二苯基-2,4-咪唑烷二酮
  参考文献：
  名称：

  Biltz, Chemische Berichte, 1908, vol. 41, p. 172,1379

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium permanganate 、 丙酮 作用下， 生成 1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one
  参考文献：
  名称：

  Biltz, Chemische Berichte, 1908, vol. 41, p. 172,1379

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-酰脲丙酸 在 盐酸 、 1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one 作用下， 以 水 、 异丙醇 为溶剂， 反应 7.0h， 生成 二氢尿嘧啶
  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

• 4,5-Dihydroxyimidazolidin-2-ones in an α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 3. α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea
  作者：G. A. Gazieva、P. V. Lozhkin、V. V. Baranov、Yu. V. Nelyubina、A. N. Kravchenko、N. N. Makhova

  DOI：10.1007/s11172-009-0348-0

  日期：2009.12

  α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea with 1,3-unsubstituted, 1,3-dialkyl-, and 1,3-dimethyl-4,5-diphenyl-4,5-dihydroxyimidazolidin-2-ones(thiones) was systematically studied. Hitherto unknown N-[2-(dimethylamino)ethyl]glycolurils and their hydrochlorides were synthesized. The yields of the target glycoluril hydrochlorides decreased on going from 1,3-H2- to 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-ones and increased with the introduction of phenyl groups at the positions 4 and 5 of the starting 4,5-dihydroxyimidazolidin-2-one. X-ray diffraction study showed that 2-[2-(dimethylamino)ethyl]glycoluril crystallizes in the form of a conglomerate.

  系统研究了 N-[2-(二甲基氨基)乙基]脲与 1,3-未取代的、1,3-二烷基和 1,3-二甲基-4,5-二苯基-4,5-二羟基咪唑烷-2-酮（亚硫酸盐）的α-脲烷基化反应。合成了迄今未知的 N-[2-（二甲基氨基）乙基]甘氨酰脲及其盐酸盐。从 1,3-H2- 到 1,3- 二烷基-4,5-二羟基咪唑烷-2-酮，目标甘糖醇盐酸盐的产率有所下降，而在起始的 4,5-二羟基咪唑烷-2-酮的第 4 和第 5 位引入苯基后，产率则有所上升。X 射线衍射研究表明，2-[2-(二甲基氨基)乙基]甘氨酰脲以聚合体形式结晶。
• 4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxyalkyl-, N-hydroxyalkyl-, and N-(aminoalkyl)ureas 4.* α-Ureidoalkylation of N-(2-acetylaminoethyl)ureas
  作者：G. A. Gazieva、P. V. Lozhkin、V. V. Baranov、A. N. Kravchenko、N. N. Makhova

  DOI：10.1007/s11172-010-0117-0

  日期：2010.3

  α-Ureidoalkylation of N-(2-acetylammoethyl)ureas with various 4,5-dihydroxyimidazoli-din-2-ones was systematically studied. Novel N-(2-acetylaminoethyl)glycolurils were obtained. Their yields were found to decrease both when moving from l,3-H2-to l,3-Alk2-4,5-dihydroxy-imidazolidin-2-ones and when increasing the size of the substituent at the second N atom in the starting acetylaminoethylurea. The higher yields were achieved with 4,5-diphenyl-4,5-dihydroxyimidazolidin-2-one as the starting compound. 2-(2-Acetylaminoethyl)-4-methylgly-coluril exhibits nootropic activity.

  系统研究了 N-(2-乙酰氨基乙基)脲与各种 4,5-二羟基咪唑-2-酮的 α-脲烷基化反应。获得了新的 N-(2-乙酰氨基乙基)甘氨酰脲。研究发现，当从 l,3-H2转变为 l,3-Alk2-4,5-二羟基咪唑啉-2-酮时，以及当增加起始乙酰氨基乙基脲中第二个 N 原子上取代基的大小时，它们的产率都会降低。以 4,5-二苯基-4,5-二羟基咪唑烷-2-酮为起始化合物的产率较高。2-(2-Acetylaminoethyl)-4-methylgly-coluril 具有促智活性。
• Synthesis and structures of 5(3H)-oxotetrahydro-1H-imidazo[4,5-c][1,2,5]thiadiazole 2,2-dioxides
  作者：G. A. Gazieva、A. N. Kravchenko、K. A. Lyssenko、R. G. Gaziev、O. V. Lebedev、N. N. Makhova

  DOI：10.1007/s11172-008-0231-4

  日期：2008.8

  The reactions of sulfamides with 4,5-dihydroxyimidazolidin-2-ones were studied at ambient and high pressure. The previously unknown derivatives of 5(3H)-oxotetrahydro-1H-imidazo-[4,5-c][1,2,5]thiadiazole 2,2-dioxide, viz., sulfo analogs of tetrahydroimidazo[4,5-d]imidazole-2,5-(1H,3H) diones (glycolurils), were synthesized. The structures of some of these compounds were established by X-ray diffraction

  在环境和高压下研究了磺酰胺与 4,5-二羟基咪唑啉-2-酮的反应。以前未知的 5(3H)-oxotetrahydro-1H-imidazo-[4,5-c][1,2,5]thiadiazole 2,2-dioxide 的衍生物，即四氢咪唑并 [4,5-d] 的磺基类似物]咪唑-2,5-(1H,3H)二酮（甘脲）被合成。其中一些化合物的结构是通过 X 射线衍射确定的。在溶剂相变条件下进行的高压反应还提供了 N-(1,3-二乙基-5-羟基-2-氧代咪唑啉-4-基)-N,N'-二烷基磺酰胺。在这些化合物中，发现了一个新的聚合体。
• Nootropic activity of N-(2-acetylaminoethyl)glycolurils
  作者：L. V. Anikina、G. A. Gazieva、A. N. Kravchenko

  DOI：10.1007/s11172-020-2799-2

  日期：2020.3

  The neurotropic activity of N-(2-acetylaminoethyl)glycoluril derivatives and their analgesic effect were studied. The nootropic activity of glycolurils was investigated for the first time, and a compound with the nootropic effect exceeding that of piracetam was revealed.

  研究了N-(2-乙酰氨基乙基)甘脲衍生物的神经活性及其镇痛作用。首次研究了甘脲的促智活性，揭示了一种促智作用超过吡拉西坦的化合物。
• 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。