Oxocane, 2-pentyl-8-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-hexynyl]- | 142285-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Oxocane, 2-pentyl-8-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-hexynyl]-
• 英文别名: (2S^*,8S^*)-2-pentyl-8-<6-(R,S)-tetrahydropyranyloxyhex-2-ynyl>oxocane
• CAS: 142285-07-2
• 化学式: C₂₃H₄₀O₃
• 分子量: 364.569
• InChiKey: KOQYDSBJSXIOBY-ZVTBYLAHSA-N

物化性质

• 沸点：
  480.2±40.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Oxocane, 2-pentyl-8-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-hexynyl]- 在 jones reagent 、 3 A molecular sieve 、 对甲苯磺酸 、 臭氧 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 cis-pseudo-gloeosporone
  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：

  2-(3-溴丙氧基)四氢-2H-吡喃 在 正丁基锂 作用下， 反应 6.25h， 生成 Oxocane, 2-pentyl-8-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-hexynyl]-
  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

文献信息

• Synthesis of medium ring ethers. Part 3. Disproof of the proposed 2,8-disubstituted oxocane structure for gloeosporone. Synthesis of pseudo-gloeosporone
  作者：Robert W. Carling、J. Stephen Clark、Andrew B. Holmes、Dirk Sartor

  DOI：10.1039/p19920000095

  日期：——

  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.