7,7-Dimethyl-5-methylene-9-phenyl-non-8-yn-1-ol | 853956-08-8

• 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: 7,7-Dimethyl-5-methylene-9-phenyl-non-8-yn-1-ol
• 英文别名: 7,7-Dimethyl-5-methylidene-9-phenylnon-8-yn-1-ol
• CAS: 853956-08-8
• 化学式: C₁₈H₂₄O
• 分子量: 256.388
• InChiKey: JXMNCASPWNOMQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  8
• 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：

  7,7-Dimethyl-5-methylene-9-phenyl-non-8-yn-1-ol 在 [Au(PPh3)](ClO4) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到10,10-Dimethyl-8-phenyl-1-oxa-spiro[5.5]undec-8-ene
  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：

  2-(5-Bromomethyl-hex-5-enyloxy)-tetrahydro-pyran 在 正丁基锂 、 四甲基乙二胺 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 7.0h， 生成 7,7-Dimethyl-5-methylene-9-phenyl-non-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