(E)-6-methyl-9-phenyl-1,1,1-trifluoronona-5-ene-2-one | 162085-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-6-methyl-9-phenyl-1,1,1-trifluoronona-5-ene-2-one
• 英文别名: (E)-1,1,1-trifluoro-6-methyl-9-phenylnon-6-en-2-one
• CAS: 162085-08-7
• 化学式: C₁₆H₁₉F₃O
• 分子量: 284.321
• InChiKey: YVANGKULIJTNCL-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-6-methyl-9-phenyl-1,1,1-trifluoronona-5-ene-2-one 在 二氯乙基铝 、 pyridinium chlorochromate 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 14.5h， 生成 4-hydroxy-10-methyl-7-oxo-4-trifluoromethyl-trans-octahydrophenanthrene
  参考文献：
  名称：

  Tandem carbonyl ene cyclization-cycloalkylation: a route to trifluoromethyl diterpenoids.

  摘要：

  A new sequential carbonyl-ene cyclizatian/cycloalkylation of trifluoromethyl ketones catalyzed by aluminum Lewis acids is described. From ketone 1, the 4-CF3-4-OH cis-octahydrophenanthrene 6 is obtained in 50 % yield. From ketone 2, with MeAlCl(2) a total stereoselective route to the 4-CF3-trans-10-methyl podocarpatrienol 8 (90 % yield) has been found. These studies also exhibited some striking results in the stereochemical outcome of ene cyclizations.

  DOI：

  10.1016/s0040-4020(01)89305-4
• 作为产物：
  描述：

  (E)-4-methyl-7-phenyl-heptan-4-ene-1-ol mesylate 在 盐酸 、 sodium amide 、 六甲基二硅氮烷 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 、 甲苯 为溶剂， 反应 96.0h， 生成 (E)-6-methyl-9-phenyl-1,1,1-trifluoronona-5-ene-2-one
  参考文献：
  名称：

  Tandem carbonyl ene cyclization-cycloalkylation: a route to trifluoromethyl diterpenoids.

  摘要：

  A new sequential carbonyl-ene cyclizatian/cycloalkylation of trifluoromethyl ketones catalyzed by aluminum Lewis acids is described. From ketone 1, the 4-CF3-4-OH cis-octahydrophenanthrene 6 is obtained in 50 % yield. From ketone 2, with MeAlCl(2) a total stereoselective route to the 4-CF3-trans-10-methyl podocarpatrienol 8 (90 % yield) has been found. These studies also exhibited some striking results in the stereochemical outcome of ene cyclizations.

  DOI：

  10.1016/s0040-4020(01)89305-4

文献信息

• Tandem carbonyl ene cyclization-cycloalkylation: a route to trifluoromethyl diterpenoids.
  作者：Ahmed Abouabdellah、Danièle Bonnet-Delpon

  DOI：10.1016/s0040-4020(01)89305-4

  日期：1994.1

  A new sequential carbonyl-ene cyclizatian/cycloalkylation of trifluoromethyl ketones catalyzed by aluminum Lewis acids is described. From ketone 1, the 4-CF3-4-OH cis-octahydrophenanthrene 6 is obtained in 50 % yield. From ketone 2, with MeAlCl(2) a total stereoselective route to the 4-CF3-trans-10-methyl podocarpatrienol 8 (90 % yield) has been found. These studies also exhibited some striking results in the stereochemical outcome of ene cyclizations.