anti-10-Hydroxyethylidenetricyclo<4.3.1.12,5>undecane | 160409-91-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: anti-10-Hydroxyethylidenetricyclo<4.3.1.12,5>undecane
• 英文别名: anti-10-Hydroxyethylidenetricyclo<4.3.1.1^2,5>undecane
• CAS: 160409-91-6
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: FCAWHROLTOTOKG-HOOLBULASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  anti-10-Hydroxyethylidenetricyclo<4.3.1.12,5>undecane 在 potassium carbonate 、 臭氧 、 三氟乙酸酐 作用下， 生成 anti-11-Oxatricyclo<4.3.2.1^2,5>dodecan-10-one
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals and Oxidative Elimination of Alicyclic Iodides

  摘要：

  The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3. The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which involves P-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.

  DOI：

  10.1021/jo00102a019
• 作为产物：
  描述：

  (1R,2R,5S,6S)-tricyclo[4.3.1.12,5]undec-3-en-10-one 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 80.0h， 生成 anti-10-Hydroxyethylidenetricyclo<4.3.1.12,5>undecane
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals and Oxidative Elimination of Alicyclic Iodides

  摘要：

  The azaallyl cation-mediated [4 + 3] cycloaddition with spiro[2.4]hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3. The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)(2)-I-2 (Suarez cleavage), which involves P-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively. Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.

  DOI：

  10.1021/jo00102a019