O-((2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl) S-methyl carbonodithioate | 1332626-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-((2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl) S-methyl carbonodithioate
• CAS: 1332626-57-9
• 化学式: C₂₇H₃₈FNO₃S₂
• 分子量: 507.734
• InChiKey: LNFDMIYVDQWDBX-IPEDAYSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  O-((2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl) S-methyl carbonodithioate 在 titanium(IV) isopropylate 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三乙基硼 、 三正丁基氢锡 、 Cyclopentylmagnesium chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 (2E,4R,6E,8E,10S,11R,12S,14R)-ethyl 15-(3-amino-5-fluorophenyl)-11,12-dimethoxy-2,4,8,10,14-pentamethylpentadeca-2,6,8-trienoate
  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 、 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.67h， 生成 O-((2S,4S,5R,6S)-1-(3-(diallylamino)-5-fluorophenyl)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl) S-methyl carbonodithioate
  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