[4R*,5R*]-4,5-dihydro-4,5-diphenyl-2-ethyl-1H-imidazole | 145144-56-5

• 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: [4R*,5R*]-4,5-dihydro-4,5-diphenyl-2-ethyl-1H-imidazole
• 英文别名: (4R,5R)-2-ethyl-4,5-diphenyl-4,5-dihydro-1H-imidazole
• CAS: 145144-56-5
• 化学式: C₁₇H₁₈N₂
• 分子量: 250.343
• InChiKey: JOLCRXPCFKIZSK-IAGOWNOFSA-N

物化性质

• 沸点：
  423.9±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [4R*,5R*]-4,5-dihydro-4,5-diphenyl-2-ethyl-1H-imidazole 在 正丁基锂 、 B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane 作用下， 反应 0.08h， 生成
  参考文献：
  名称：

  9-BBN triflate mediated stereoselective alkylation of 2-alkyl imidazolines with tetrahydrofurans

  摘要：

  Nucleophilic attack of deprotonated imidazolines 3 or 4 on tetrahydrofuran derivatives in the presence of 9-BBN triflate can afford the corresponding alkylated products 7 with moderate to good stereoselectivities.

  DOI：

  10.1016/s0040-4039(00)79135-0
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到[4R*,5R*]-4,5-dihydro-4,5-diphenyl-2-ethyl-1H-imidazole
  参考文献：
  名称：

  Intramolecular bromo-amination of 1,4-cyclohexadieneaminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (−)-γ-lycorane

  摘要：

  环己烯-2,5-二烯基-1-甲醛与光学纯1,2-二芳基-1,2-二胺的反应，再经过分子内溴氨化，产生了一锅法在环己烷体系中对两种烯烃的辨别，这一过程用于(−)-γ-利克贺因的不对称合成。

  DOI：

  10.1039/b512161b

文献信息

• Intramolecular bromo-amination of 1,4-cyclohexadieneaminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (−)-γ-lycorane
  作者：Hiromichi Fujioka、Kenichi Murai、Yusuke Ohba、Hideki Hirose、Yasuyuki Kita

  DOI：10.1039/b512161b

  日期：——

  The reaction of cyclohexa-2,5-dienyl-1-methylaldehyde and optically pure 1,2-diaryl-1,2-diamine followed by intramolecular bromo-amination produced a one-pot discrimination of two olefins in the cyclohexane system, which was used for the asymmetric synthesis of (−)-γ-lycorane.

  环己烯-2,5-二烯基-1-甲醛与光学纯1,2-二芳基-1,2-二胺的反应，再经过分子内溴氨化，产生了一锅法在环己烷体系中对两种烯烃的辨别，这一过程用于(−)-γ-利克贺因的不对称合成。
• A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes
  作者：Hiromichi Fujioka、Kenichi Murai、Yusuke Ohba、Atsushi Hiramatsu、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2005.02.025

  日期：2005.3

  The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0 degrees C to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and many functional groups such as halogens, nitrites, and esters can exist. (c) 2005 Elsevier Ltd. All rights reserved.
• One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates
  作者：Hiromichi Fujioka、Kenichi Murai、Ozora Kubo、Yusuke Ohba、Yasuyuki Kita

  DOI：10.1016/j.tet.2006.11.007

  日期：2007.1

  Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective. (c) 2006 Published by Elsevier Ltd.
• 9-BBN triflate mediated stereoselective alkylation of 2-alkyl imidazolines with tetrahydrofurans
  作者：Peter I. Dalko、Yves Langlois

  DOI：10.1016/s0040-4039(00)79135-0

  日期：1992.9

  Nucleophilic attack of deprotonated imidazolines 3 or 4 on tetrahydrofuran derivatives in the presence of 9-BBN triflate can afford the corresponding alkylated products 7 with moderate to good stereoselectivities.