5-亚氨基-1,3-二甲基咪唑烷-2,4-二酮 | 10319-56-9

• 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: 5-亚氨基-1,3-二甲基咪唑烷-2,4-二酮
• 英文名称: 1,3-dimethyl-5-imino-imidazolidin-2,4-dione
• 英文别名: 5-imino-1,3-dimethylimidazolidine-2,4-dione；1,3-dimethyl-5-iminohydantoin；5-imino-1,3-dimethyl-imidazolidine-2,4-dione；1,3-Dimethyl-parabansaeure；Propazon
• CAS: 10319-56-9
• 化学式: C₅H₇N₃O₂
• 分子量: 141.129
• InChiKey: OELLJQGSVGDWJK-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  165.5±23.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-亚氨基-1,3-二甲基咪唑烷-2,4-二酮 在 盐酸 作用下， 以 水 为溶剂， 生成 N,N'-二甲基仲班酸
  参考文献：
  名称：

  6-氮杂嘧啶衍生物的新型环收缩

  摘要：

  在有和没有亲电子试剂的情况下，将-100氮杂嘧啶嘧啶的衍生物在-100°C下锂化。适当的6-氮杂嘧啶与叔丁基锂和二异丙基氨基锂的反应由于环收缩而得到化合物5和6。化合物5的结构不可否认地通过X射线分析确定。讨论了1,2,4-三嗪向咪唑的新型环转化的机理。

  DOI：

  10.1016/s0040-4020(00)00479-8
• 作为产物：
  描述：

  咖啡因 在 manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride 、 ammonium acetate 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 13.0h， 生成 5-亚氨基-1,3-二甲基咪唑烷-2,4-二酮
  参考文献：
  名称：

  Oxidation of caffeine with hydrogen peroxide catalyzed by metalloporphyrins

  摘要：

  The biomimetic oxidation of caffeine with hydrogen peroxide using metalloporphyrins as catalysts, which are known to be good biomimetic models of cytochrome P450 enzymes, is investigated. The two manganese porphyrins tested, chloro[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]manganese(III), [Mn(TDCPP)Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(III), [Mn(TPEPP)Cl], afford high conversions of caffeine for all substrate/catalyst molar ratios. Selectivity was found to be dependent on the catalyst employed, and a new spiro racemic compound is described and fully characterized in the solid state from X-ray diffraction studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.139

文献信息

• Reactions of α-Aminoacetonitriles with Isothiocyanates. Synthesis of 1,3-Disubstituted 5-Imino-2-thiohydantoins
  作者：Takeshi Kinoshita、Hiroko Watanabe、Sadao Sato、Chihiro Tamura

  DOI：10.1246/bcsj.53.442

  日期：1980.2

  The reactions of α-aminoacetonitriles with isothiocyanates gave 1-cyanomethyl-1,3-disubstituted thioureas or 1,3-disubstituted 4-amino-4-imidazoline-2-thiones depending upon the reaction conditions. In the presence of polar organic solvents such as methanol the former products were easily cyclized to the latter. 1,3-Disubstituted 4-amino-4-imidazoline-2-thiones were autoxidized in methanol affording 1,3-disubstituted 5-imino-2-thiohydantoins.

  α-氨基乙腈与异硫氰酸酯的反应可以在不同条件下得到1-氰甲基-1,3-二取代硫脲或1,3-二取代4-氨基-4-咪唑啉-2-硫酮。在极性有机溶剂如甲醇的存在下，前者产物容易环化为后者。1,3-二取代4-氨基-4-咪唑啉-2-硫酮在甲醇中自动氧化生成1,3-二取代5-亚氨基-2-硫脲。
• KINOSHITA TAKESHI; WATANABE HIROKO; SATO SADAO; TAMURA CHIHIRO, BULL. CHEM. SOC. JAP., 1980, 53, NO 2, 442-445
  作者：KINOSHITA TAKESHI、 WATANABE HIROKO、 SATO SADAO、 TAMURA CHIHIRO

  DOI：——

  日期：——
• NAGAI YASUTAKA; MAKI AKIO; KANDA HISASHI; NATSUKA KAGAYAKI; UMEMOTO SUSUM+, CHEM. AND PHARM. BULL., 1976, 24, NO 6, 1179-1188
  作者：NAGAI YASUTAKA、 MAKI AKIO、 KANDA HISASHI、 NATSUKA KAGAYAKI、 UMEMOTO SUSUM+

  DOI：——

  日期：——
• Novel Ring Contraction of 6-Azauracil Derivatives
  作者：Hanna Wojtowicz-Rajchel、Joanna Szczepkowska-Sztolcman、Andrzej Katrusiak、Krzysztof Golankiewicz

  DOI：10.1016/s0040-4020(00)00479-8

  日期：2000.8

  Derivatives of 6-azauracil were lithiated at −100°C with and without an electrophilic agent. Reactions of appropriate 6-azauracils with t-butyllithium and lithium diisopropylamide gave, as a result of a ring contraction, compounds 5 and 6. The structure of compound 5 was undeniably established by X-ray analysis. A mechanism of the novel ring transformation of 1,2,4-triazines to imidazoles is discussed

  在有和没有亲电子试剂的情况下，将-100氮杂嘧啶嘧啶的衍生物在-100°C下锂化。适当的6-氮杂嘧啶与叔丁基锂和二异丙基氨基锂的反应由于环收缩而得到化合物5和6。化合物5的结构不可否认地通过X射线分析确定。讨论了1,2,4-三嗪向咪唑的新型环转化的机理。
• Oxidation of caffeine with hydrogen peroxide catalyzed by metalloporphyrins
  作者：Cláudia M.B. Neves、Mário M.Q. Simões、Isabel C.M.S. Santos、Fernando M.J. Domingues、M. Graça P.M.S. Neves、Filipe A. Almeida Paz、Artur M.S. Silva、José A.S. Cavaleiro

  DOI：10.1016/j.tetlet.2011.03.139

  日期：2011.6

  The biomimetic oxidation of caffeine with hydrogen peroxide using metalloporphyrins as catalysts, which are known to be good biomimetic models of cytochrome P450 enzymes, is investigated. The two manganese porphyrins tested, chloro[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]manganese(III), [Mn(TDCPP)Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(III), [Mn(TPEPP)Cl], afford high conversions of caffeine for all substrate/catalyst molar ratios. Selectivity was found to be dependent on the catalyst employed, and a new spiro racemic compound is described and fully characterized in the solid state from X-ray diffraction studies. (C) 2011 Elsevier Ltd. All rights reserved.