6,6-Dimethyl-4-methylene-8-phenyl-oct-7-yn-1-ol | 853956-04-4

• 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: 6,6-Dimethyl-4-methylene-8-phenyl-oct-7-yn-1-ol
• 英文别名: 6,6-Dimethyl-4-methylidene-8-phenyloct-7-yn-1-ol
• CAS: 853956-04-4
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: CLOPDZJCHJOHET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  6,6-Dimethyl-4-methylene-8-phenyl-oct-7-yn-1-ol 在 [Au(PPh3)](ClO4) 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 9,9-Dimethyl-7-phenyl-1-(toluene-4-sulfonyl)-1-aza-spiro[4.5]dec-7-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-(6,6-Dimethyl-4-methylene-8-phenyl-oct-7-ynyloxy)-tetrahydro-pyran 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以0.11 g的产率得到6,6-Dimethyl-4-methylene-8-phenyl-oct-7-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