3a,8a-dihydroxy-1,3-dimethyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one

• 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-dimethyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one
• 英文别名: 3a,8b-Dihydroxy-1,3-dimethyl-2-sulfanylideneindeno[1,2-d]imidazol-4-one；3a,8b-dihydroxy-1,3-dimethyl-2-sulfanylideneindeno[1,2-d]imidazol-4-one
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: KJDXYEVLIFUZTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水合茚三酮 、 N,N'-二甲基硫脲 反应 2.0h， 以100%的产率得到3a,8a-dihydroxy-1,3-dimethyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one
  参考文献：
  名称：

  Quantitative Reaction Cascades of Ninhydrin in the Solid State

  摘要：

  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.

  DOI：

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

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.