5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(4-chloromethyl-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester | 251354-69-5

• 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: 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(4-chloromethyl-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester
• CAS: 251354-69-5
• 化学式: C₂₅H₂₈ClNO₈
• 分子量: 505.952
• InChiKey: DKZAWQYWLJOUHA-NQRVTCLYSA-N

物化性质

• 沸点：
  688.4±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120.22
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(4-chloromethyl-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(4-azidomethyl-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-Chloromethyl-7-((3aR,4R,7R,7aR)-7-methoxy-2,2,6,6-tetramethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-chromen-2-one 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(4-chloromethyl-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