(2'R,4'S,5'R,6'S)-4'-hydroxy-5'-methyl-2',6'-bis(4-(trifluoromethyl)phenyl)dispiro[indene-2,1'-cyclohexane-3',2''-indene]-1,1'',3,3''-tetraone | 1438625-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (2'R,4'S,5'R,6'S)-4'-hydroxy-5'-methyl-2',6'-bis(4-(trifluoromethyl)phenyl)dispiro[indene-2,1'-cyclohexane-3',2''-indene]-1,1'',3,3''-tetraone
• CAS: 1438625-96-7
• 化学式: C₃₇H₂₄F₆O₅
• 分子量: 662.585
• InChiKey: XYVQPBJOCVOSQP-WQKTZRJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  48.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.51
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(4-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione 、 丙醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以42%的产率得到(2'R,4'S,5'R,6'S)-4'-hydroxy-5'-methyl-2',6'-bis(4-(trifluoromethyl)phenyl)dispiro[indene-2,1'-cyclohexane-3',2''-indene]-1,1'',3,3''-tetraone
  参考文献：
  名称：

  Synthesis of Fully Substituted Dispirocyclohexanes by Organocatalytic [2 + 2 + 2] Annulation Strategy between 2-Arylideneindane-1,3-diones and Aldehydes

  摘要：

  An interesting organocatalytic reaction between 2-arylideneindane-1,3-diones and aldehydes has been developed that gives fully substituted cyclohexanes that bear two all-carbon quaternary centers. The dispirocyclohexanes were obtained in reasonable-to-good chemical yields and with high stereoselectivities (>95:5 d.r. and up to 99% ee) using a catalytic amount of commercially available alpha,alpha-L-diphenylprolinol trimethylsilyl ether (5 mol %) and DABCO (20 mol %) in DMF at -20 degrees C. The reaction proceeds through a unique Michael/Michael/aldol reaction that requires 2 equiv of the 2-arylideneindane-1,3-dione.

  DOI：

  10.1021/ol4011689