1,3,3a,8a-tetrahydro-3a,8a-hydroxy-2-thioindeno<1,2-d>imidazole-2,8-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1,3,3a,8a-tetrahydro-3a,8a-hydroxy-2-thioindeno<1,2-d>imidazole-2,8-dione
• 英文别名: 3a,8a-dihydroxy-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one；3a,8a-dihydroxy-2-thioxo-2,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(1H)-one；3a,8a-dihydroxy-2-thio-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-one；1,3,3a,8a-tetrahydro-3a,8a-hydroxy-2-thioindeno[1,2-d]imidazole-2,8-dione；3a,8b-dihydroxy-2-sulfanylidene-1,3-dihydroindeno[1,2-d]imidazol-4-one
• 化学式: C₁₀H₈N₂O₃S
• mdl: MFCD00777210
• 分子量: 236.251
• InChiKey: ANUGYOJFCCLRRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：
  114
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水合茚三酮 以 水 为溶剂， 反应 2.05h， 生成 1,3,3a,8a-tetrahydro-3a,8a-hydroxy-2-thioindeno<1,2-d>imidazole-2,8-dione
  参考文献：
  名称：

  水中新的多组分反应：通过茚三酮-丙二腈加合物与多种 N-双亲核试剂反应，轻松合成 1,3-二氧代-2-茚满二苯胺杂环支架和茚并喹喔啉

  摘要：

  我们在此报道了一种通过茚三酮、丙二腈和各种二胺在水介质中的一锅三组分反应合成咪唑啉-2-亚基-茚二酮、嘧啶-2-亚基-茚二酮和茚并喹喔啉衍生物的高效绿色方法。无催化剂条件。在室温下，反应时间短，目标产物收率高（73-98%）。该方案的显着优点是后处理简单、无需柱色谱、产率良好至优异、反应快速和绿色溶剂。

  DOI：

  10.1039/d2ra06469c

文献信息

• A Green Approach to Synthesize and in vitro Antimicrobial Activity of Indeno-Imidazole Derivatives and Ninhydrin-Nucleophile Adducts
  作者：Samia Rifat、Khorshada Jahan、U.K.R. Romman、Kawsari Akhter、Md. Ershad Halim

  DOI：10.14233/ajchem.2016.19775

  日期：——

  Ninhydrin (1) reacted with weak nitrogen nucleophiles (2a-2f) in the presence of H2O/EtOH medium to give the corresponding indeno-imidazole derivatives (3a-3d) and ninhydrin-nucleophile adducts (3e-3f). The structures of the compounds (3a-3f) were confirmed by their UV, IR, 1H NMR, 13C NMR spectra and elemental analyses. The synthesized compounds were evaluated for their antimicrobial activity by Kirby-Bauer disk diffusion method. Most of the compounds showed good to moderate antimicrobial activity.

  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。
• Structural elucidation of adducts formed by ninhydrin with indoles and thiourea by 13C-NMR spectroscopy
  作者：Nithiananda Chatterjie、Ralph A. Stephani、Charles H. Strom

  DOI：10.1002/jps.2600691221

  日期：1980.12

  prepared by the reaction of ninhydrin with indole and 2,5-dimethylindole. The structures of these 1:1 adducts were assigned as 3-(2-hydroxy-2-indane-1,3-dionyl)indole and 3-(2-hydroxy-2-indane-1,3-dionyl)-2,5-dimethylindole, respectively, on the basis of spectral data including 13C-NMR evidence. 13C-NMR also was used to confirm the structure of a thiourea-ninhydrin adduct as a substituted thioindeno[1

  通过茚三酮与吲哚和2,5-二甲基吲哚的反应制备缩合产物。这些1：1加合物的结构被指定为3-（2-羟基-2-茚满-1,3-二酰）吲哚和3-（2-羟基-2-茚满-1,3-二酰）-2， 5-二甲基吲哚分别基于包括13 C-NMR证据在内的光谱数据确定。13 C-NMR也用于证实作为取代的硫代腺苷[1,2-d]咪唑-2,8-二酮的硫脲-茚三酮加合物的结构。
• Synthesis, crystal structure analysis and DFT studies of 3a,8a-Dihydroxy-2-thioxo-2,3,3a,8a-tetrahydroindeno[1,2- d ]imidazol-8(1 H )-one
  作者：D. Ramarajan、K. Tamilarasan、S. Sudha

  DOI：10.1016/j.molstruc.2017.03.045

  日期：2017.7

  characterization was performed by the application of FTIR and FT-Raman spectroscopic techniques. In order to support the experimental results, density functional theory calculations have been carried out using B3LYP/6-31G(d,p) method. The vibrational assignment of the fundamentals was proposed on the basis of potential energy distribution (PED) calculations. The stability of the molecule due to hyper-conjugative

  摘要 合成了3a,8a-Dihydroxy-2-thioxo-2,3,3a,8a-四氢茚并[1,2-d]咪唑-8(1 H)-酮(NTU)晶体，并用X对其进行了结构表征。 -射线衍射法。通过应用 FTIR 和 FT-Raman 光谱技术进行光谱表征。为了支持实验结果，使用 B3LYP/6-31G(d,p) 方法进行了密度泛函理论计算。在势能分布 (PED) 计算的基础上提出了基本原理的振动分配。通过自然键轨道分析研究了由于超共轭相互作用和电荷离域引起的分子稳定性。已根据最高占据分子轨道 (HOMO) 和最低未占据分子轨道 (LUMO) 解释了电荷转移特性。HOMO 和 LUMO 之间的小能隙是导致非线性光学特性的分子内电荷转移的指标。一阶超极化结果证实了分子的非线性光学活性。进行分子静电势 (MEP) 分析以预测分子的反应位点。理论结果与实验值吻合良好。一阶超极化结果证实了分子的非线性光学活性。进行分子静电势
• 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.
• Synthesis, supramolecularity and in vitro antimicrobial activity of 3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-one
  作者：Raza Murad Ghalib、Rokiah Hashim、Solhe F. Alshahateet、Sayed Hasan Mehdi、Othman Sulaiman、Vikneswaran Murugaiyah、Claira Arul Aruldass

  DOI：10.1016/j.molstruc.2011.08.042

  日期：2011.11

  The solid-state structure of 3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-one (3) was determined using X-ray single crystal technique. Its non-covalent interactions were analyzed carefully in terms of crystal engineering and supramolecular chemistry. Multiple sulfur-hydrogen and oxygen-hydrogen interactions are present in the structure, most commonly involving bifurcated H S H motifs which resulted in formation interesting centrosymmetric dimmers. This compound demonstrated comparable antimicrobial activity to that of clinically used antimicrobial agents against selected microorganisms. (C) 2011 Elsevier B.V. All rights reserved.