(1R,7S)-1,10,10-trimethyl-4-naphthalen-2-yl-3,5-diazatricyclo[5.2.1.0(2,6)]deca-2(6),3-diene | 1110673-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,7S)-1,10,10-trimethyl-4-naphthalen-2-yl-3,5-diazatricyclo[5.2.1.0(2,6)]deca-2(6),3-diene
• 英文别名: (1R,7S)-1,10,10-trimethyl-4-naphthalen-1-yl-3,5-diazatricyclo[5.2.1.02,6]deca-2(6),3-diene
• CAS: 1110673-07-8
• 化学式: C₂₁H₂₂N₂
• 分子量: 302.419
• InChiKey: DVMRMRKBEDCYFZ-IERDGZPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-萘甲基胺 、 (1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 反应 1.0h， 以52%的产率得到(1R,7S)-1,10,10-trimethyl-4-naphthalen-2-yl-3,5-diazatricyclo[5.2.1.0(2,6)]deca-2(6),3-diene
  参考文献：
  名称：

  Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction

  摘要：

  Two classes of terpene derivatives (diketones and monoximes) were condensed into annulated terpeneimidazoles using two general methods. Method A, involving the condensation of terpene diketones and aldehydes, gave lower yields than Method B, which employed terpene monoximes and amines. The mechanism of Method B is discussed. Using both methods, overall 11 new imidazole ligands were synthesized and fully characterized. The molecular structures of the side product 16 and intermediate 4b were also characterized by X-ray analysis. Regarding la, N-methylation and subsequent ortho-lithiation and quenching with diphenylphosphinechloride were proven. The synthesized ligands were tested in the Henry reaction providing reaction times 24-72 h and enantioselectivities up to 32% especially for the pyridine 2-substituted ligands 1c, 2c, 3b and N,P-ligand 17. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.026

文献信息

• Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction
  作者：Jiří Kulhánek、Filip Bureš、Petr Šimon、W. Bernd Schweizer

  DOI：10.1016/j.tetasy.2008.10.026

  日期：2008.11

  Two classes of terpene derivatives (diketones and monoximes) were condensed into annulated terpeneimidazoles using two general methods. Method A, involving the condensation of terpene diketones and aldehydes, gave lower yields than Method B, which employed terpene monoximes and amines. The mechanism of Method B is discussed. Using both methods, overall 11 new imidazole ligands were synthesized and fully characterized. The molecular structures of the side product 16 and intermediate 4b were also characterized by X-ray analysis. Regarding la, N-methylation and subsequent ortho-lithiation and quenching with diphenylphosphinechloride were proven. The synthesized ligands were tested in the Henry reaction providing reaction times 24-72 h and enantioselectivities up to 32% especially for the pyridine 2-substituted ligands 1c, 2c, 3b and N,P-ligand 17. (C) 2008 Elsevier Ltd. All rights reserved.