(Z)-9-<(Methoxymethoxy)methyl>-3-methylene-4-<(triisopropylsilyl)oxy>-9-cyclododecen-1-yne | 155261-54-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-9-<(Methoxymethoxy)methyl>-3-methylene-4-<(triisopropylsilyl)oxy>-9-cyclododecen-1-yne
• 英文别名: [(7Z)-8-(methoxymethoxymethyl)-2-methylidenecyclododec-7-en-3-yn-1-yl]oxy-tri(propan-2-yl)silane
• CAS: 155261-54-4
• 化学式: C₂₅H₄₄O₃Si
• 分子量: 420.708
• InChiKey: WHNNVCDTSRMFCC-IWIPYMOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-9-<(Methoxymethoxy)methyl>-3-methylene-4-<(triisopropylsilyl)oxy>-9-cyclododecen-1-yne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以88%的产率得到(Z)-8-<(Methoxymethoxy)methyl>-2-methylene-7-cyclododecen-3-yn-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
• 作为产物：
  描述：

  1-庚炔-3,7-二醇 在 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 、 四乙基溴化铵 、 氢溴酸 、 碘 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 三乙胺 、 甲苯 、 乙腈 为溶剂， 反应 56.66h， 生成 (Z)-9-<(Methoxymethoxy)methyl>-3-methylene-4-<(triisopropylsilyl)oxy>-9-cyclododecen-1-yne
  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.