[2(1'RS),4R*,5R*]-2-(3'-tert-butoxy-1'-phenylpropyl)-4,5-dihydro-4,5-diphenyl-1H-imidazole

• 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: [2(1'RS),4R*,5R*]-2-(3'-tert-butoxy-1'-phenylpropyl)-4,5-dihydro-4,5-diphenyl-1H-imidazole
• 英文别名: (4S,5S)-2-[3-[(2-methylpropan-2-yl)oxy]-1-phenylpropyl]-4,5-diphenyl-4,5-dihydro-1H-imidazole
• 化学式: C₂₈H₃₂N₂O
• 分子量: 412.575
• InChiKey: DKCAZIGMLHUCNW-WIXBZOCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 [2(1'RS),4R*,5R*]-2-(3'-tert-butoxy-1'-phenylpropyl)-4,5-dihydro-4,5-diphenyl-1H-imidazole 在 仲丁基锂 、 B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.47h， 生成 [5SR,5(4'R*,5'R*)]-7-tert-butoxy-5-(4',5'-dihydro-4',5'-diphenyl-1H-imidazol-2'-yl)-5-phenylheptan-1-ol 、 [5RS,5(4'R*,5'R*)]-7-tert-butoxy-5-(4',5'-dihydro-4',5'-diphenyl-1H-imidazol-2'-yl)-5-phenylheptan-1-ol
  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：

  ethyl 2-phenylacetimidate hydrochloride 在 仲丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 21.42h， 生成 [2(1'RS),4R*,5R*]-2-(3'-tert-butoxy-1'-phenylpropyl)-4,5-dihydro-4,5-diphenyl-1H-imidazole
  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.