4,4'-((2'R,4'S,5'R,6'S)-4'-hydroxy-5'-methyl-1,1'',3,3''-tetraoxo-1,1'',3,3''-tetrahydrodispiro[indene-2,1'-cyclohexane-3',2''-indene]-2',6'-diyl)dibenzonitrile | 1438625-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4,4'-((2'R,4'S,5'R,6'S)-4'-hydroxy-5'-methyl-1,1'',3,3''-tetraoxo-1,1'',3,3''-tetrahydrodispiro[indene-2,1'-cyclohexane-3',2''-indene]-2',6'-diyl)dibenzonitrile
• CAS: 1438625-97-8
• 化学式: C₃₇H₂₄N₂O₅
• 分子量: 576.608
• InChiKey: UAVRLDUICORPSP-LIENLCNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  44.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  136.09
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-((1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)methyl)benzonitrile 、 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 48.0h， 以57%的产率得到4,4'-((2'R,4'S,5'R,6'S)-4'-hydroxy-5'-methyl-1,1'',3,3''-tetraoxo-1,1'',3,3''-tetrahydrodispiro[indene-2,1'-cyclohexane-3',2''-indene]-2',6'-diyl)dibenzonitrile
  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