N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4'-(p-bromophenyl)-6'-diphenylpyrimidin-2'-yl)thiourea | 1127559-79-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4'-(p-bromophenyl)-6'-diphenylpyrimidin-2'-yl)thiourea
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[4-(4-bromophenyl)-6-phenylpyrimidin-2-yl]carbamothioylamino]oxan-2-yl]methyl acetate
• CAS: 1127559-79-8
• 化学式: C₃₁H₃₁BrN₄O₉S
• 分子量: 715.579
• InChiKey: HQZOQMMIERFHPE-XYPQWYOHSA-N

物化性质

• 熔点：
  223-224 °C(Solvent: Ethanol; Toluene)
• 沸点：
  770.6±70.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  196
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4'-(p-bromophenyl)-6'-diphenylpyrimidin-2'-yl)thiourea 、 溴乙酸乙酯 在 氯仿 作用下， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((Z)-3-(4-(4-bromophenyl)-6-phenylpyrimidin-2-yl)-4-oxothiazolidin-2-ylidene)amino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 、 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((Z)-2-((4-(4-bromophenyl)-6-phenylpyrimidin-2-yl)imino)-4-oxothiazolidin-3-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Reaction ofN-(Per-O-acetyl-β-D-glucopyranosyl)-Nʼ-(4ʼ,6ʼ-diarylpyrimidine-2ʼ-yl)thioureas with Ethyl Bromoacetate

  摘要：

  一些含有嘧啶环的新2-亚硫酰胺噻唑啉-4-酮已经通过取代的N-(per-O-乙酰-β-D-葡萄糖吡喃基)-N'-(4',6'-二芳基嘧啶-2'-基)硫脲与溴乙酸乙酯反应合成。同分异构体产物的结构已通过红外光谱、1H和13C核磁共振等光谱方法得到确认。

  DOI：

  10.1155/2011/348479
• 作为产物：
  描述：

  乙酰溴葡糖 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4'-(p-bromophenyl)-6'-diphenylpyrimidin-2'-yl)thiourea
  参考文献：
  名称：

  Reaction ofN-(Per-O-acetyl-β-D-glucopyranosyl)-Nʼ-(4ʼ,6ʼ-diarylpyrimidine-2ʼ-yl)thioureas with Ethyl Bromoacetate

  摘要：

  一些含有嘧啶环的新2-亚硫酰胺噻唑啉-4-酮已经通过取代的N-(per-O-乙酰-β-D-葡萄糖吡喃基)-N'-(4',6'-二芳基嘧啶-2'-基)硫脲与溴乙酸乙酯反应合成。同分异构体产物的结构已通过红外光谱、1H和13C核磁共振等光谱方法得到确认。

  DOI：

  10.1155/2011/348479

文献信息

• Synthesis of N-tetra-O-acetyl-β-d-glucopyranosyl-N′-(4′,6′-diarylpyrimidin-2′-yl)thioureas
  作者：Nguyen Dinh Thanh、Nguyen Thi Thanh Mai

  DOI：10.1016/j.carres.2009.09.002

  日期：2009.11

  Some 2-amino-4,6-diarylpyrimidines 2 have been prepared from substituted benzylideneacetophenones and guanidine hydrochloride in the presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. N-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas 4 have been synthesized by reaction of per-O-acetylated glucopyranosyl isothiocyanate 1 and substituted 2-amino-4,6-diarylpyrimidines 2. Two different methods have been used, namely, refluxing in anhydrous dioxane and solvent-free microwave-assisted coupling. The second procedure afforded higher yields in much shorter reaction times. The compounds 2 and 4 were tested for their antibacterial and antifungal activities in vitro against Staphylococcus epidermidis, Enterobacter aerogenes and Candida albicans by disc diffusion method. (C) 2009 Elsevier Ltd. All rights reserved.
• Reaction of<i>N</i>-(Per-<i>O</i>-acetyl-β-<i>D</i>-glucopyranosyl)-<i>N</i>ʼ-(4ʼ,6ʼ-diarylpyrimidine-2ʼ-yl)thioureas with Ethyl Bromoacetate
  作者：Nguyen Dinh Thanh

  DOI：10.1155/2011/348479

  日期：——

  Some new 2-iminothiazolidin-4-ones having pyrimidine ring have been synthesized by reaction of substitutedN-(per-O-acetyl-β-D-glucopyranosyl)-Nʼ-(4ʼ,6ʼ-diarylpyrimidine-2ʼ-yl)thioureas with ethyl bromoacetate. The structure of isomeric products has been confirmed by spectroscopic methods, such as IR,¹H and¹³C NMR.

  一些含有嘧啶环的新2-亚硫酰胺噻唑啉-4-酮已经通过取代的N-(per-O-乙酰-β-D-葡萄糖吡喃基)-N'-(4',6'-二芳基嘧啶-2'-基)硫脲与溴乙酸乙酯反应合成。同分异构体产物的结构已通过红外光谱、1H和13C核磁共振等光谱方法得到确认。