9-(β-D-glucopyranosyloxy)-7-methyl-2,3-dihydrocyclopenta[c]chromen-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-(β-D-glucopyranosyloxy)-7-methyl-2,3-dihydrocyclopenta[c]chromen-4-one
• 英文别名: 7-Methyl-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-YL]oxy}-1H,2H,3H,4H-cyclopenta[C]chromen-4-one；7-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one
• 化学式: C₁₉H₂₂O₈
• 分子量: 378.379
• InChiKey: AAAACIDXVXFWLZ-WIMVFMHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  9-hydroxy-7-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 9-(β-D-glucopyranosyloxy)-7-methyl-2,3-dihydrocyclopenta[c]chromen-4-one
  参考文献：
  名称：

  Modified Coumarins. 17. Synthesis and Anticoagulant Activity of 3,4-Cycloannelated Coumarin D-Glycopyranosides

  摘要：

  通过羟基香豆素钾盐和乙酰溴糖缩合合成了含有葡萄糖、半乳糖、木糖和阿拉伯糖的 3,4-环缩合香豆素 O-吡喃糖苷。7-(β-D-半乳糖吡喃糖氧基)-2,3-二氢环戊并[c]色烯-4-酮、3-(β-D-木糖吡喃糖氧基)-7,8,9,10-四氢苯并[c]色烯-6-酮和 3-(α-D-阿拉伯吡喃糖氧基)苯并[c]色烯-6-酮表现出独特的抗凝血活性。

  DOI：

  10.1007/s10600-005-0194-8

文献信息

• Modified Coumarins. 12. Synthesis of 3,4-Cycloannelated Coumarin  -D-Glucopyranosides
  作者：Ya. L. Garazd、M. M. Garazd、V. P. Khilya

  DOI：10.1023/b:conc.0000025455.68950.36

  日期：2004.1

  O-beta-D-Glucopyranosides were synthesized using 3,4-cycloannelated hydroxycoumarins as aglycons. Phenolic hydroxyls were O-glycosylated via condensation of coumarin potassium salts with acetobromoglucose in homogeneous medium and in a liquid-liquid system using a phase-transfer catalyst.
• Modified Coumarins. 17. Synthesis and Anticoagulant Activity of 3,4-Cycloannelated Coumarin D-Glycopyranosides
  作者：Ya. L. Garazd、E. M. Kornienko、L. N. Maloshtan、M. M. Garazd、V. P. Khilya

  DOI：10.1007/s10600-005-0194-8

  日期：2005.9

  3,4-Cyclocondensed coumarin O-glycopyranosides containing glucose, galactose, xylose, and arabinose were synthesized by condensation of potassium salts of hydroxycoumarins and acetobromosugars. 7-(β-D-Galactopyranosyloxy)-2,3-dihydrocyclopenta[c]chromen-4-one, 3-(β-D-xylopyranosyloxy)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one, and 3-(α-D-arabinopyranosyloxy)benzo[c]chromen-6-one exhibited distinct anticoagulant activity.

  通过羟基香豆素钾盐和乙酰溴糖缩合合成了含有葡萄糖、半乳糖、木糖和阿拉伯糖的 3,4-环缩合香豆素 O-吡喃糖苷。7-(β-D-半乳糖吡喃糖氧基)-2,3-二氢环戊并[c]色烯-4-酮、3-(β-D-木糖吡喃糖氧基)-7,8,9,10-四氢苯并[c]色烯-6-酮和 3-(α-D-阿拉伯吡喃糖氧基)苯并[c]色烯-6-酮表现出独特的抗凝血活性。