(1R,7S)-1,10,10-trimethyl-4-phenyl-3,5-diazatricyclo[5.2.1.0(2,6)]deca-2(6),3-diene | 1027006-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1R,7S)-1,10,10-trimethyl-4-phenyl-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-phenyl-3,5-diazatricyclo[5.2.1.02,6]deca-2(6),3-diene
• CAS: 1027006-04-7
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: JHOIIPNHWPQJDC-PXAZEXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,7S)-1,10,10-trimethyl-4-phenyl-3,5-diazatricyclo[5.2.1.0(2,6)]deca-2(6),3-diene 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 以95%的产率得到(4R,7S)-1,4,8,8-tetramethyl-2-phenyl-4,5,6,7-tetrahydro-1H-4,7-methanobenzo[d]imidazole
  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
• 作为产物：
  描述：

  (1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 、 苄胺 反应 1.0h， 以55%的产率得到(1R,7S)-1,10,10-trimethyl-4-phenyl-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.
• One-step and solvent-free synthesis of fused terpene-pyrazines
  作者：Filip Bureš、Jiří Kulhánek、Miroslav Ludwig

  DOI：10.3998/ark.5550190.0011.226

  日期：——

  Solvent-free condensation reactions were carried out by heating terpene-monooximes with an excess of amines. Employing camphor- and nopinone-derived monooximes, two classes of terpene-fused pyrazine derivatives were synthesized. Besides being solvent-free, the described one-step procedure can be directed towards terpene-fused imidazole or pyrazine derivatives. Whereas the reaction worked well with arylmethanamines bearing a (hetero)aromatic substituent at the alpha-carbon, alkylamines afforded only imino-oximes. A possible reaction path is presented.