5-[N-(2-aminophenyl)ethanimidoyl]-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione | 932731-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[N-(2-aminophenyl)ethanimidoyl]-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione
• 英文别名: 4-hydroxy-5-[N-(2-hydroxyphenyl)ethanimidoyl]-2H-1,3-thiazine- 2,6(3H)-dione
• CAS: 932731-28-7
• 化学式: C₁₂H₁₁N₃O₃S
• 分子量: 277.304
• InChiKey: WCJXCLOKUBJTRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  108.54
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-[N-(2-aminophenyl)ethanimidoyl]-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione 、 苯甲醛 在 三氟乙酸 作用下， 以 丙醇 为溶剂， 生成 4-hydroxy-5-(2-phenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)-2H-1,3-thiazine-2,6(3H)-dione
  参考文献：
  名称：

  Azines and azoles: CXXVI. First example of a novel heterocyclic system: Pyrimido[1,6-a][1,5]benzodiazepines

  摘要：

  4-Hydroxy-5-(2-R-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones readily undergo acylation at the N-1 atom of the benzodiazepine system by the action of acetic anhydride. Heating of the acetylated products in boiling dimethylformamide leads to the formation of 75-93% of the corresponding 7-acetyl-6-R-6,7-dihydropyrimido[1,6-a][1,5]benzodiazepine-1,3-diones that are derivatives of hitherto unknown fused heterocyclic system, pyrimido[1,6-a][1,5]benzodiazepine. 4-Hydroxy-5-(2-R-2,3-dihydro-1H1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones are converted into 1-(2-aminophenyl)-6-(2-R-vinyl)uracils on heating in boiling DMF.

  DOI：

  10.1134/s1070363207120146
• 作为产物：
  描述：

  邻苯二胺 、 5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以72%的产率得到5-[N-(2-aminophenyl)ethanimidoyl]-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione
  参考文献：
  名称：

  基于 5-acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione 的三齿 NNO Schiff 贱金属配合物的合成、光谱研究、DFT 计算、抗菌和抗肿瘤活性

  摘要：

  摘要 通过5-乙酰基-4-羟基-2 H -1,3-噻嗪-2,6(3 H )-二酮与邻苯二胺缩合制备了新型席夫碱配体。Cu(II)、Ni(II)、Co(II)、VO(IV)、Zn(II)、Cd(II)和UO 2 (VI)配合物的制备和表征基于元素分析、IR、( 1 H 和 13 C) NMR、电子、ESR 和质谱；磁、摩尔电导测量以及热重分析。席夫碱配体的配位位点是酚氧、偶氮甲碱氮和氨基氮；其中配体作为一元三齿。所有结果都表明，除了 Ni(II)- 和 VO(IV)- 配合物具有 1:2（金属：配体）化学计量外，所有化合物都具有 1:1（金属：配体）化学计量。除了Cu(II)配合物呈方形平面排列和UO 2 (VI)呈五边形双锥排列外，金属配合物呈八面体几何结构。使用 Coats-Redfern 方法计算配体及其金属配合物的热力学参数。配体及其复合物针对一些革兰氏阴性和革兰氏阳性细菌和真菌菌株

  DOI：

  10.1016/j.molstruc.2019.07.010

文献信息

• Synthesis of New Derivatives of 5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione
  作者：A. V. Velikorodov、A. S. Zukhayrayeva、V. P. Osipova、M. A. Polovinkina

  DOI：10.1134/s1070428019120121

  日期：2019.12

  5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione reacted with cyclohexyl and benzyl (4-aminophenyl)carbamates in boiling ethanol in the presence of a catalytic amount of glacial acetic acid to give the corresponding Schiff bases, cyclohexyl and benzyl (4-[(E)-1-(4-hydroxy-2,6-dioxo-3,6-dihydro-2H-1,3-thiazin-5-yl)ethylidene]amino}phenyl)carbamates. Heating of the latter in dimethylformamide for 2 h was accompanied by evolution of COS with the formation of cyclohexyl and benzyl 4-[6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]phenyl}carbamates. The condensation of the title compound with benzene-1,2-diamine in propan-2-ol, followed by addition of 5-arylfuran-2-carbaldehyde and trifluoroacetic acid afforded 5-(2-5-[4-bromo(nitro)phenyl]furan-2-yl}-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-4-hydroxy-2H-1,3-thiazine-2,6(3H)-diones. 5-((E)-3-5-[4-Bromo(nitro)phenyl]furan-2-yl}prop-2-enoyl)-4-hydroxy-2H-1,3-thiazine-2,6(3H)-diones were synthesized by condensation of 5-acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione with 5-[4-bromo(nitro)phenyl]furan-2-carbaldehydes in chloroform in the presence of catalytic amounts of pyridine and piperidine.