(4S,5S)-3-Benzyl-2-((S)-5-benzyloxy-1-methyl-1-phenyl-pentyl)-1-methyl-4,5-diphenyl-4,5-dihydro-3H-imidazol-1-ium; iodide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5S)-3-Benzyl-2-((S)-5-benzyloxy-1-methyl-1-phenyl-pentyl)-1-methyl-4,5-diphenyl-4,5-dihydro-3H-imidazol-1-ium; iodide
• 英文别名: (4S,5S)-1-benzyl-3-methyl-4,5-diphenyl-2-[(2S)-2-phenyl-6-phenylmethoxyhexan-2-yl]-4,5-dihydroimidazol-3-ium;iodide
• 化学式: C₄₂H₄₅N₂O*I
• 分子量: 720.737
• InChiKey: AHIYFWTVTDAWCZ-KYHBSJMISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  15.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-3-Benzyl-2-((S)-5-benzyloxy-1-methyl-1-phenyl-pentyl)-1-methyl-4,5-diphenyl-4,5-dihydro-3H-imidazol-1-ium; iodide 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.08h， 生成 (S)-6-benzyloxy-2-methyl-2-phenylhexanal
  参考文献：
  名称：

  Stereoselective Synthesis of Quaternary Benzylic Carbons Using C₂ Symmetric Imidazolines and Tetrahydrofuran as Electrophile

  摘要：

  Alkylative ring opening of tetrahydrofuran in the presence of 9-BBN triflate is studied. Dianions derived from Ct symmetric imidazolines induce excellent to modest acyclic diastereoselectivity to form quaternary benzylic centers, using the 9-BBN triflate/THF system or methyl iodide as electrophiles. The direction of the stereoinduction is consistent in both cases. Absolute configuration for the newly created stereogenic center was established by chemical correlation. Low-temperature NMR studies of the dilithiated intermediates 42 and 43 suggest the presence of N- and C-metalated compounds, where the metal-bearing benzylic carbon is sp(3) hybridized.

  DOI：

  10.1021/jo980289r
• 作为产物：
  描述：

  [5S-5(4'S,5'S)]-5-(4',5'-dihydro-4',5'-diphenyl-1H-imidazol-2'-yl)-5-phenylhexan-1-ol 在 四丁基碘化铵 、 sodium hydride 、 barium(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (4S,5S)-3-Benzyl-2-((S)-5-benzyloxy-1-methyl-1-phenyl-pentyl)-1-methyl-4,5-diphenyl-4,5-dihydro-3H-imidazol-1-ium; iodide
  参考文献：
  名称：

  Stereoselective Synthesis of Quaternary Benzylic Carbons Using C₂ Symmetric Imidazolines and Tetrahydrofuran as Electrophile

  摘要：

  Alkylative ring opening of tetrahydrofuran in the presence of 9-BBN triflate is studied. Dianions derived from Ct symmetric imidazolines induce excellent to modest acyclic diastereoselectivity to form quaternary benzylic centers, using the 9-BBN triflate/THF system or methyl iodide as electrophiles. The direction of the stereoinduction is consistent in both cases. Absolute configuration for the newly created stereogenic center was established by chemical correlation. Low-temperature NMR studies of the dilithiated intermediates 42 and 43 suggest the presence of N- and C-metalated compounds, where the metal-bearing benzylic carbon is sp(3) hybridized.

  DOI：

  10.1021/jo980289r

文献信息

• Stereoselective Synthesis of Quaternary Benzylic Carbons Using <i>C</i><i>₂</i> Symmetric Imidazolines and Tetrahydrofuran as Electrophile
  作者：Peter I. Dalko、Yves Langlois

  DOI：10.1021/jo980289r

  日期：1998.11.1

  Alkylative ring opening of tetrahydrofuran in the presence of 9-BBN triflate is studied. Dianions derived from Ct symmetric imidazolines induce excellent to modest acyclic diastereoselectivity to form quaternary benzylic centers, using the 9-BBN triflate/THF system or methyl iodide as electrophiles. The direction of the stereoinduction is consistent in both cases. Absolute configuration for the newly created stereogenic center was established by chemical correlation. Low-temperature NMR studies of the dilithiated intermediates 42 and 43 suggest the presence of N- and C-metalated compounds, where the metal-bearing benzylic carbon is sp(3) hybridized.