3-phenyl-7-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one | 1227736-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenyl-7-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one
• CAS: 1227736-33-5
• 化学式: C₃₀H₃₁NO₁₂
• 分子量: 597.576
• InChiKey: MASVASFQJZXVTQ-RHBSMATHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  165.75
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-7-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以56%的产率得到3-phenyl-7-methoxy-4-(β-D-glucopyranosyloxy)quinolin-2(1H)-one
  参考文献：
  名称：

  Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

  摘要：

  A comparative study for selective glucosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl-alpha-D-glucopyranosyl bromide, beta-D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl-alpha-D-glucopyranosyl bromide with Cs(2)CO(3) in CH(3)CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones were deacetylated into 4-(beta-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et(3)N in MeOH. In some instances the deacetylation was accompanied by the sugar-aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon resonances as well as assignment of anomeric configuration for all the products under investigation were performed by 1D and 2D NMR spectroscopy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.01.023
• 作为产物：
  描述：

  4-羟基-7-甲氧基-3-苯基喹啉-2(1H)-酮 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以42%的产率得到3-phenyl-7-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one
  参考文献：
  名称：

  Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

  摘要：

  A comparative study for selective glucosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl-alpha-D-glucopyranosyl bromide, beta-D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl-alpha-D-glucopyranosyl bromide with Cs(2)CO(3) in CH(3)CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl-beta-D-glucopyranosyloxy)quinolin-2(1H)-ones were deacetylated into 4-(beta-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et(3)N in MeOH. In some instances the deacetylation was accompanied by the sugar-aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon resonances as well as assignment of anomeric configuration for all the products under investigation were performed by 1D and 2D NMR spectroscopy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.01.023