(E)-5,7,7-Trimethyl-9-phenyl-non-4-en-8-yn-1-ol | 853956-16-8

• 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: (E)-5,7,7-Trimethyl-9-phenyl-non-4-en-8-yn-1-ol
• 英文别名: (E)-5,7,7-trimethyl-9-phenylnon-4-en-8-yn-1-ol
• CAS: 853956-16-8
• 化学式: C₁₈H₂₄O
• 分子量: 256.388
• InChiKey: OXKWCBZTRNIVRH-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-5,7,7-Trimethyl-9-phenyl-non-4-en-8-yn-1-ol 在 gold(III) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以98%的产率得到(S)-2-((S)-1,4,4-Trimethyl-2-phenyl-cyclopent-2-enyl)-tetrahydro-furan
  参考文献：
  名称：

  Gold-Catalyzed Assembly of Heterobicyclic Systems

  摘要：

  We have described an efficient gold-catalyzed double cyclization of 1,5-enynes to afford a range of heterobicyclic compounds, including oxabicylclo[3.2.1]octenes, azabicyclo[3.2.1]octenes, oxaspiro[5.4]decene, azaspiro[5.4]decene, oxaspiro[5.5]undecene, oxabicyclo[4.3.0]nonene, azabicyclo[4.3.0]nonene, and oxabicyclo[4.4.0]decene. The mechanism of this reaction is proposed to involve a chemoselective gold-based alkyne activation, carbocyclization, intramolecular nucleophilic addition, followed by protodemetalation. The most notable aspect of this process is the efficient and diastereospecific interception of the reactive intermediate of the initial 6-endo-dig (or 5-endo-dig) cyclization with either oxygen- or nitrogen-based nucleophiles.

  DOI：

  10.1021/ja051110e
• 作为产物：
  描述：

  3-methyl-1-triisopropylsilylbutyne 在 正丁基锂 、 四甲基乙二胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 (E)-5,7,7-Trimethyl-9-phenyl-non-4-en-8-yn-1-ol
  参考文献：
  名称：

  Gold-Catalyzed Assembly of Heterobicyclic Systems

  摘要：

  We have described an efficient gold-catalyzed double cyclization of 1,5-enynes to afford a range of heterobicyclic compounds, including oxabicylclo[3.2.1]octenes, azabicyclo[3.2.1]octenes, oxaspiro[5.4]decene, azaspiro[5.4]decene, oxaspiro[5.5]undecene, oxabicyclo[4.3.0]nonene, azabicyclo[4.3.0]nonene, and oxabicyclo[4.4.0]decene. The mechanism of this reaction is proposed to involve a chemoselective gold-based alkyne activation, carbocyclization, intramolecular nucleophilic addition, followed by protodemetalation. The most notable aspect of this process is the efficient and diastereospecific interception of the reactive intermediate of the initial 6-endo-dig (or 5-endo-dig) cyclization with either oxygen- or nitrogen-based nucleophiles.

  DOI：

  10.1021/ja051110e