3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-methoxyaniline | 1332626-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-methoxyaniline
• CAS: 1332626-22-8
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: BCEVLVREXTWLHH-VVVONTASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  53.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-methoxyaniline 在 titanium(IV) isopropylate 、 lithium hydroxide monohydrate 、 水 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 Cyclopentylmagnesium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 53.67h， 生成
  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：

  (2S,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-ynal 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三乙基硼 、 叔丁基锂 、 三正丁基氢锡 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 7.67h， 生成 3-((2R,4S,5R,6S)-4,5-dimethoxy-2,6-dimethylnon-7-yn-1-yl)-5-methoxyaniline
  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