4-Chloromethyl-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one | 251354-67-3

• 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-Chloromethyl-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one
• CAS: 251354-67-3
• 化学式: C₁₉H₂₃ClO₇
• 分子量: 398.84
• InChiKey: FUDBSYNFFSFXSP-BURFUSLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  98.36
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-Chloromethyl-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-pyran-2-yloxy)-8-methyl-chromen-2-one 在 CoCl₂ 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [(3R,4S,5R,6R)-5-hydroxy-3-methoxy-2,2-dimethyl-6-[8-methyl-2-oxo-4-(1H-1,2,4-triazol-5-ylsulfanylmethyl)chromen-7-yl]oxyoxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
  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88%的产率得到4-Chloromethyl-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