(S)-N-(pyrrolidin-2-ylmethyl)-1H-benzo[d]imidazol-2-amine | 1338826-13-3

• 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: (S)-N-(pyrrolidin-2-ylmethyl)-1H-benzo[d]imidazol-2-amine
• 英文别名: N-[[(2S)-pyrrolidin-2-yl]methyl]-1H-benzimidazol-2-amine
• CAS: 1338826-13-3
• 化学式: C₁₂H₁₆N₄
• 分子量: 216.286
• InChiKey: NIUPTHBYISMKOP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯苯并咪唑 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 20.0~200.0 ℃ 、101.33 kPa 条件下， 反应 64.0h， 生成 (S)-N-(pyrrolidin-2-ylmethyl)-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Novel pyrrolidine-aminobenzimidazole bifunctional organocatalysts for asymmetric nitro-Michael reactions in brine

  摘要：

  A new family of bifunctional organocatalysts with conformationally rigid H-bond donors was successfully synthesized and applied to the aqueous phase Michael reactions of cyclohexanone with nitroolefins. The corresponding products were obtained with high enantioselectivities (up to 99% ee) and diastereoselectivies (up to 99/1 dr) in the presence of a slight excess of Michael donors in brine at room temperature. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.002
• 作为试剂：
  描述：

  1-(4-氟苯基)-2-硝基乙烯 、 环己酮 在 (S)-N-(pyrrolidin-2-ylmethyl)-1H-benzo[d]imidazol-2-amine 、 大茴香酸 作用下， 反应 8.25h， 以85%的产率得到(2S)-2-[(1R)-1-(4-氟苯基)-2-硝基乙基]环己烷-1-酮
  参考文献：
  名称：

  Novel pyrrolidine-aminobenzimidazole bifunctional organocatalysts for asymmetric nitro-Michael reactions in brine

  摘要：

  A new family of bifunctional organocatalysts with conformationally rigid H-bond donors was successfully synthesized and applied to the aqueous phase Michael reactions of cyclohexanone with nitroolefins. The corresponding products were obtained with high enantioselectivities (up to 99% ee) and diastereoselectivies (up to 99/1 dr) in the presence of a slight excess of Michael donors in brine at room temperature. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.002

文献信息

• Novel pyrrolidine-aminobenzimidazole bifunctional organocatalysts for asymmetric nitro-Michael reactions in brine
  作者：Jian Lin、Hua Tian、Yi-Jun Jiang、Wen-Bo Huang、Liang-Yu Zheng、Suo-Qin Zhang

  DOI：10.1016/j.tetasy.2011.08.002

  日期：2011.7

  A new family of bifunctional organocatalysts with conformationally rigid H-bond donors was successfully synthesized and applied to the aqueous phase Michael reactions of cyclohexanone with nitroolefins. The corresponding products were obtained with high enantioselectivities (up to 99% ee) and diastereoselectivies (up to 99/1 dr) in the presence of a slight excess of Michael donors in brine at room temperature. (C) 2011 Elsevier Ltd. All rights reserved.