3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione | 22431-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione
• 英文别名: 3a,8a-dihydroxy-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione；3a,8a-Dihydroxy-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazol-2,8-dion；3a,8a-Dihydroxy-1,3,3a,8a-tetrahydro-indeno<1,2-d>imidazol-2,8-dion；Ninhydrylharnstoff；3a,8b-dihydroxy-1,3-dihydroindeno[1,2-d]imidazole-2,4-dione
• CAS: 22431-00-1
• 化学式: C₁₀H₈N₂O₄
• 分子量: 220.185
• InChiKey: GFRINMJNUSPSGI-UHFFFAOYSA-N

物化性质

• 熔点：
  217-220 °C
• 沸点：
  620.9±55.0 °C(Predicted)
• 密度：
  1.815±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 以44%的产率得到
  参考文献：
  名称：

  Sarra; Stephani, Medicinal Chemistry Research, 2000, vol. 10, # 2, p. 81 - 91

  摘要：

  DOI：
• 作为产物：
  描述：

  水合茚三酮 、 尿素 以 水 为溶剂， 反应 0.83h， 以98%的产率得到3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione
  参考文献：
  名称：

  A Green Approach to Synthesize and in vitro Antimicrobial Activity of Indeno-Imidazole Derivatives and Ninhydrin-Nucleophile Adducts

  摘要：

  水合茚三酮（1）在H2O/EtOH介质中与弱氮亲核试剂（2a-2f）反应，生成了相应的吲哚并咪唑衍生物（3a-3d）和水合茚三酮-亲核试剂加合物（3e-3f）。通过UV、IR、1H NMR、13C NMR光谱以及元素分析确认了化合物（3a-3f）的结构。合成化合物通过Kirby-Bauer纸片扩散法评估了其抗菌活性，其中大多数化合物显示出较好至中等的抗菌活性。

  DOI：

  10.14233/ajchem.2016.19775

文献信息

• Quantitative Reaction Cascades of Ninhydrin in the Solid State
  作者：Gerd Kaupp、M. Reza Naimi-Jamal、Jens Schmeyers

  DOI：10.1002/1521-3765(20020201)8:3<594::aid-chem594>3.0.co;2-5

  日期：2002.2.1

  Crystalline ninhydrin (1) undergoes waste-free solid-state cascade reactions with dimedone, L-proline, three omicron-phenyienediamines, omicron-mercaptoaniline, two ureas, three thioureas, and methyl 3-aminocrotonate. The yields are quantitative and give pure crystalline products without workup just by milling stoichiometric mixtures of the crystalline reagents. The structures of the new and the previously obtained products with lower yields from solutions are established or confirmed by spectroscopic data and density functional calculations at the B3LYP/6-31G* level. The success of 3- and 4-cascade reactions in the crystal without melting is unusual and of unmatched atom economy. They are mechanistically investigated with atomic force microscopy techniques (AFM) on six different faces of 1 when omicron-phenylenediamine was the reagent (substitution, elimination, cyclization, elimination) and interpreted on the basis of known crystal structure data. Strict correlations to the crystal packings are observed. The characteristic surface features grow to mum heights in some cases at distances of 0.5 mm. from the contact edge of the reacting crystals. The waste-free and easy syntheses of highly functionalized (C=O; O-H, C=N) heterocycles or of a tetraketone are also of interest for synthetic use.
• Transformations of substituted tetrahydro-8h-indeno[1,2-d]imidazoles in concentrated sulfuric acid
  作者：A. K. Aren、F. A. Grunsberg、I. K. Yurgevitsa

  DOI：10.1007/bf00945645

  日期：1974.4
• Macromolecular compositions comprising indene-derivatives, preparation thereof, and use thereof
  申请人：Stichting voor de Technische Wetenschappen

  公开号：US20200368721A1

  公开（公告）日：2020-11-26

  The present invention relates to a method for preparing a macromolecular composition comprising indene-derivatives. The invention also relates to the macromolecular compositions per se, and to methods of using the macromolecular compositions. The macromolecular compositions are useful for undergoing subsequent reactions with small molecules.