(2S^*,8R^*)-2-pentyl-8-(trifluoromethylsulfonyloxy)methyloxocane | 142285-12-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2S^*,8R^*)-2-pentyl-8-(trifluoromethylsulfonyloxy)methyloxocane
• CAS: 142285-12-9
• 化学式: C₁₄H₂₅F₃O₄S
• 分子量: 346.411
• InChiKey: BIYSMSCTGBJMLN-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S^*,8R^*)-2-pentyl-8-(trifluoromethylsulfonyloxy)methyloxocane 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 32.33h， 生成 (2R^*,8S^*)-2-(6-hydroxyhex-2-ynyl)-8-pentyloxocane
  参考文献：
  名称：

  Synthesis of medium ring ethers. Part 3. Disproof of the proposed 2,8-disubstituted oxocane structure for gloeosporone. Synthesis of pseudo-gloeosporone

  摘要：

  Synthesis of the cis- and trans-2,8-disubstituted oxocane derivatives 2 and 3 (carrying the unusual gamma,delta-diketohexanecarboxylic acid side chain) by ozonolysis of the alkynes 14 and 18 (prepared respectively from the alcohols 11 and 15) demonstrated unequivocally that neither of these compounds nor their hydroxy-gamma-lactone ring (lactol) tautomers 1 corresponded to the naturally occurring fungal self germination inhibitor gloeosporone. A study of 4,5-dioxohexanoic itself 9 revealed a remarkably low tendency to exist as its hydroxy-gamma-lactone (lactol) tautomer 10.

  DOI：

  10.1039/p19920000095
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (2R^*,8S^*)-2-hydroxymethyl-8-pentyloxocane 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到(2S^*,8R^*)-2-pentyl-8-(trifluoromethylsulfonyloxy)methyloxocane
  参考文献：
  名称：

  Synthesis of medium ring ethers. Part 3. Disproof of the proposed 2,8-disubstituted oxocane structure for gloeosporone. Synthesis of pseudo-gloeosporone

  摘要：

  Synthesis of the cis- and trans-2,8-disubstituted oxocane derivatives 2 and 3 (carrying the unusual gamma,delta-diketohexanecarboxylic acid side chain) by ozonolysis of the alkynes 14 and 18 (prepared respectively from the alcohols 11 and 15) demonstrated unequivocally that neither of these compounds nor their hydroxy-gamma-lactone ring (lactol) tautomers 1 corresponded to the naturally occurring fungal self germination inhibitor gloeosporone. A study of 4,5-dioxohexanoic itself 9 revealed a remarkably low tendency to exist as its hydroxy-gamma-lactone (lactol) tautomer 10.

  DOI：

  10.1039/p19920000095