(1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)cyclohexane-1,2-diamine | 1355991-91-1

• 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)cyclohexane-1,2-diamine
• CAS: 1355991-91-1
• 化学式: C₁₅H₁₆F₆N₄
• 分子量: 366.309
• InChiKey: BSFQOWQGUNMIRC-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.73
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-(2-nitro-3,5-bis(trifluoromethyl)phenyl)acetamide 在 palladium 10% on activated carbon 、 水 、 氢气 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.83h， 生成 (1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)cyclohexane-1,2-diamine 、 (1R,2R)-N1,N2-bis(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)cyclohexane-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