(S,E)-ethyl 2,4-dimethylhept-2-en-6-ynoate | 1332626-15-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S,E)-ethyl 2,4-dimethylhept-2-en-6-ynoate
• CAS: 1332626-15-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: CUDXUGRYOUYBEQ-WKMLFNHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S,E)-ethyl 2,4-dimethylhept-2-en-6-ynoate 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：

  (S)-2-methyl-5-trimethylsilyl-pent-4-ynal 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S,E)-ethyl 2,4-dimethylhept-2-en-6-ynoate
  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