(2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-ol | 1332626-55-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-ol
• CAS: 1332626-55-7
• 化学式: C₂₅H₃₆FNO₃
• 分子量: 417.564
• InChiKey: GZYQUMXTHPSQIK-FWQGXIHCSA-N

物化性质

• 沸点：
  509.6±50.0 °C(predicted)
• 密度：
  1.049±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-ol 在 三乙基硼 、 三正丁基氢锡 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.67h， 生成 N,N-diallyl-3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-fluoroaniline
  参考文献：
  名称：

  Convergent Synthesis and Discovery of a Natural Product-Inspired Paralog-Selective Hsp90 Inhibitor

  摘要：

  A convergent synthesis of benzoquinone ansamycin analogs is described that proceeds by a sequence of metallacycle-mediated alkyne-alkyne coupling, followed by site- and stereoselective dihydroxylation and global carbamate formation. These studies have led to (1) validation of alkyne-alkyne coupling to produce geldanamycin analogs that lack the problematic quinone, (2) the discovery that C6-C7 bis-carbamate functionality is compatible with Hsp90 inhibition, and (3) the identification of 1 as a nonquinone geldanamycin-inspired paralog-selective Hsp90 inhibitor.

  DOI：

  10.1021/ol2019828
• 作为产物：
  描述：

  3-氟-5-溴苯胺 在 正丁基锂 、 potassium carbonate 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-ol
  参考文献：
  名称：

  Convergent Synthesis and Discovery of a Natural Product-Inspired Paralog-Selective Hsp90 Inhibitor

  摘要：

  A convergent synthesis of benzoquinone ansamycin analogs is described that proceeds by a sequence of metallacycle-mediated alkyne-alkyne coupling, followed by site- and stereoselective dihydroxylation and global carbamate formation. These studies have led to (1) validation of alkyne-alkyne coupling to produce geldanamycin analogs that lack the problematic quinone, (2) the discovery that C6-C7 bis-carbamate functionality is compatible with Hsp90 inhibition, and (3) the identification of 1 as a nonquinone geldanamycin-inspired paralog-selective Hsp90 inhibitor.

  DOI：

  10.1021/ol2019828