4-(2-Bromo-ethoxy)-3-chloro-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one | 251354-74-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(2-Bromo-ethoxy)-3-chloro-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one
• CAS: 251354-74-2
• 化学式: C₂₀H₂₄BrClO₈
• 分子量: 507.763
• InChiKey: CLWXLSXUWGVSQE-FCZZECIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  107.59
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(2-Bromo-ethoxy)-3-chloro-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one 在 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-[3-chloro-4-(2-dimethylamino-ethoxy)-8-methyl-2-oxo-2H-chromen-7-yloxy]-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Structure-activity relationship in two series of aminoalkyl substituted coumarin inhibitors of gyrase B

  摘要：

  Two series of aminosubstituted coumarins were synthesised and evaluated in vitro as inhibitors of DNA gyrase and as potential antibacterials. Novel novobiocin-like coumarins, 4-(dialkylamino)-methylcoumarins and 4-((2-alkylamino)ethoxy)coumarins, were discovered as gyrase B inhibitors with promising antibacterial activity in vitro. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00492-8
• 作为产物：
  描述：

  4-(2-Bromo-ethoxy)-7-(tert-butyl-diphenyl-silanyloxy)-8-methyl-chromen-2-one 在 potassium fluoride 、 氢氟酸 、 氯 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(2-Bromo-ethoxy)-3-chloro-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one
  参考文献：
  名称：

  Structure-activity relationship in two series of aminoalkyl substituted coumarin inhibitors of gyrase B

  摘要：

  Two series of aminosubstituted coumarins were synthesised and evaluated in vitro as inhibitors of DNA gyrase and as potential antibacterials. Novel novobiocin-like coumarins, 4-(dialkylamino)-methylcoumarins and 4-((2-alkylamino)ethoxy)coumarins, were discovered as gyrase B inhibitors with promising antibacterial activity in vitro. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00492-8