(1R,2R,4S)-2-(1H-benzimidazol-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol | 192316-17-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4S)-2-(1H-benzimidazol-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 192316-17-9
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: HUCRLJRJBVDMCX-JECHBYEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S)-2-(1H-benzimidazol-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 、 二溴甲烷 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以50%的产率得到spiro[1(R),3,3-trimethyl[2.2.1]heptyl-2(S),5'-1H,3H-oxazolo[3,4-a]benzimidazole]
  参考文献：
  名称：

  Asymmetric induction using chiral 1,2,4-triazole and benzimidazole derivatives

  摘要：

  Lithiated N-substituted 1,2,4-triazoles 3 and 8 and benzimidazole 11 reacted with (1R)-fenchone to give derivatives 5c, 9 and 12 in good yields as single diastereoisomers. (S)-Lactic acid 16 reacted with o-phenylenediamine 15 to give optically pure (S)-2-(I-hydroxyethyl)benzimidazole 17 (85%). Ring closures converted the fenchone derivative 12 into novel tricyclic fused benzimidazoles 13 and 14, and converted oxazolidine derivative 17 into compound 18 in yields of 50-70% as single diastereoisomers. Lithiated derivative 18 was alkylated to give compound 19 as a single diastereoisomer in high yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00155-9
• 作为产物：
  描述：

  苯并咪唑 在 正丁基锂 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (1R,2R,4S)-2-(1H-benzimidazol-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Asymmetric induction using chiral 1,2,4-triazole and benzimidazole derivatives

  摘要：

  Lithiated N-substituted 1,2,4-triazoles 3 and 8 and benzimidazole 11 reacted with (1R)-fenchone to give derivatives 5c, 9 and 12 in good yields as single diastereoisomers. (S)-Lactic acid 16 reacted with o-phenylenediamine 15 to give optically pure (S)-2-(I-hydroxyethyl)benzimidazole 17 (85%). Ring closures converted the fenchone derivative 12 into novel tricyclic fused benzimidazoles 13 and 14, and converted oxazolidine derivative 17 into compound 18 in yields of 50-70% as single diastereoisomers. Lithiated derivative 18 was alkylated to give compound 19 as a single diastereoisomer in high yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00155-9