6-Methylene-11-(tetrahydropyranyloxy)-5-<(triisopropylsilyl)oxy>-7-undecyn-1-ol | 155261-47-5

• 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: 6-Methylene-11-(tetrahydropyranyloxy)-5-<(triisopropylsilyl)oxy>-7-undecyn-1-ol
• 英文别名: 6-Methylidene-11-(oxan-2-yloxy)-5-tri(propan-2-yl)silyloxyundec-7-yn-1-ol
• CAS: 155261-47-5
• 化学式: C₂₆H₄₈O₄Si
• 分子量: 452.75
• InChiKey: IUPUTKNIYMRVFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Methylene-11-(tetrahydropyranyloxy)-5-<(triisopropylsilyl)oxy>-7-undecyn-1-ol 在 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 13.25h， 生成 Methyl 13-(tetrahydropyranyloxy)-2-(dimethylphosphono)-8-methylene-7-<(triisopropylsilyl)oxy>-9-tridecynoate
  参考文献：
  名称：

  Synthesis of the Pseudopterane and Furanocembrane Ring Systems by Intraannular Cyclization of .beta.- and .gamma.-Alkynyl Allylic Alcohols

  摘要：

  The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.

  DOI：

  10.1021/jo00086a018
• 作为产物：
  描述：

  1-庚炔-3,7-二醇 在 吡啶 、 2,6-二甲基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 四乙基溴化铵 、 氢溴酸 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 、 三乙胺 、 甲苯 为溶剂， 反应 6.58h， 生成 6-Methylene-11-(tetrahydropyranyloxy)-5-<(triisopropylsilyl)oxy>-7-undecyn-1-ol
  参考文献：
  名称：

  Synthesis of the Pseudopterane and Furanocembrane Ring Systems by Intraannular Cyclization of .beta.- and .gamma.-Alkynyl Allylic Alcohols

  摘要：

  The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.

  DOI：

  10.1021/jo00086a018

文献信息

• Synthesis of the Pseudopterane and Furanocembrane Ring Systems by Intraannular Cyclization of .beta.- and .gamma.-Alkynyl Allylic Alcohols
  作者：James A. Marshall、William J. DuBay

  DOI：10.1021/jo00086a018

  日期：1994.4

  The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.