(1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-N2,N2-dimethylcyclohexane-1,2-diamine | 1355991-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-N2,N2-dimethylcyclohexane-1,2-diamine
• 英文别名: (1R,2R)-1-N-[4,6-bis(trifluoromethyl)-1H-benzimidazol-2-yl]-2-N,2-N-dimethylcyclohexane-1,2-diamine
• CAS: 1355991-65-9
• 化学式: C₁₇H₂₀F₆N₄
• 分子量: 394.363
• InChiKey: UKBPCTCTNBSVQO-DGCLKSJQSA-N

物化性质

• 沸点：
  427.7±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)cyclohexane-1,2-diamine 在 甲酸 作用下， 以 水 为溶剂， 反应 16.0h， 以61%的产率得到(1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-N2,N2-dimethylcyclohexane-1,2-diamine
  参考文献：
  名称：

  Chiral 2-aminobenzimidazole bifunctional organocatalysts: effect of di-CF3 and TFA on catalytic mechanisms

  摘要：

  (S,S)-trans-Cyclohexanediamine-5,7-di-CF3-benzimidazole (3b) was developed as a new chiral bifunctional organocatalyst and successfully applied to Michael addition of diethyl malonate to nitroolefins (up to 99%, 98% ee) under neutral condition. Systematic investigation on the catalytic mechanism revealed that the role of the guanidine moiety and the dimethylamine moiety in catalysts might be reversed with respect to Bronsted/Lewis acidic or basic functionalities, depending on the reaction conditions (neutral or TFA co-catalyst). Generally, di-CF3 group substituted 2-aminobenzimidazole catalysts in neutral condition and non-substituted 2-aminobenzimidazole catalysts in co-catalyst (TFA) condition give high chemical yield and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.021
• 作为试剂：
  描述：

  β-硝基苯乙烯 、 丙二酸二乙酯 在 (1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-N2,N2-dimethylcyclohexane-1,2-diamine 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以87%的产率得到(R)-1,3-diethyl 2-(2-nitro-1-phenylethyl)malonate
  参考文献：
  名称：

  Chiral 2-aminobenzimidazole bifunctional organocatalysts: effect of di-CF3 and TFA on catalytic mechanisms

  摘要：

  (S,S)-trans-Cyclohexanediamine-5,7-di-CF3-benzimidazole (3b) was developed as a new chiral bifunctional organocatalyst and successfully applied to Michael addition of diethyl malonate to nitroolefins (up to 99%, 98% ee) under neutral condition. Systematic investigation on the catalytic mechanism revealed that the role of the guanidine moiety and the dimethylamine moiety in catalysts might be reversed with respect to Bronsted/Lewis acidic or basic functionalities, depending on the reaction conditions (neutral or TFA co-catalyst). Generally, di-CF3 group substituted 2-aminobenzimidazole catalysts in neutral condition and non-substituted 2-aminobenzimidazole catalysts in co-catalyst (TFA) condition give high chemical yield and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.021

文献信息

• Chiral 2-aminobenzimidazole bifunctional organocatalysts: effect of di-CF3 and TFA on catalytic mechanisms
  作者：Myungmo Lee、Lei Zhang、Yohan Park、Hyeung-geun Park

  DOI：10.1016/j.tet.2011.12.021

  日期：2012.2

  (S,S)-trans-Cyclohexanediamine-5,7-di-CF3-benzimidazole (3b) was developed as a new chiral bifunctional organocatalyst and successfully applied to Michael addition of diethyl malonate to nitroolefins (up to 99%, 98% ee) under neutral condition. Systematic investigation on the catalytic mechanism revealed that the role of the guanidine moiety and the dimethylamine moiety in catalysts might be reversed with respect to Bronsted/Lewis acidic or basic functionalities, depending on the reaction conditions (neutral or TFA co-catalyst). Generally, di-CF3 group substituted 2-aminobenzimidazole catalysts in neutral condition and non-substituted 2-aminobenzimidazole catalysts in co-catalyst (TFA) condition give high chemical yield and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.