(1R,3S)-3-Methyl-1-phenyl-3H-benzo[4,5]imidazo[1,2-c]oxazole | 192316-24-8

• 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,3S)-3-Methyl-1-phenyl-3H-benzo[4,5]imidazo[1,2-c]oxazole
• 英文别名: (1R,3S)-3-methyl-1-phenyl-1,3-dihydro-[1,3]oxazolo[3,4-a]benzimidazole
• CAS: 192316-24-8
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: ZDWOGMUBLBPDCD-MEDUHNTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3S)-3-Methyl-1-phenyl-3H-benzo[4,5]imidazo[1,2-c]oxazole 在 盐酸 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 为溶剂， 反应 52.0h， 生成 (2R)-2-(1H-benzimidazo-2-yl)-1-hexan-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of 2-(α-hydroxyalkyl)benzimidazoles

  摘要：

  Lithiated oxazolo[3,4-a]benzimidazole 4 reacted with various alkyl halides to give oxazolo[3,4-a]benzimidazoles 5a-d in good yields as single diastereoisomers. (R)-Benzimidazol-2-y1 carbinols 6a-d were obtained upon hydrolysis under acidic conditions of 1H,3H-oxazolo[3,4-a]benzimidazole derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00202-x
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 (alphas)-(9ci)-alpha-甲基-1H-苯并咪唑-2-甲醇 在 对甲苯磺酸 作用下， 反应 24.0h， 以50%的产率得到(1R,3S)-3-Methyl-1-phenyl-3H-benzo[4,5]imidazo[1,2-c]oxazole
  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

文献信息

• Asymmetric induction using chiral 1,2,4-triazole and benzimidazole derivatives
  作者：Alan R. Katritzky、Diana C. Aslan、Peter Leeming、Peter J. Steel

  DOI：10.1016/s0957-4166(97)00155-9

  日期：1997.5

  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.
• Stereoselective synthesis of 2-(α-hydroxyalkyl)benzimidazoles
  作者：Alan R. Katritzky、Diana C. Aslan、Daniela C. Oniciu

  DOI：10.1016/s0957-4166(98)00202-x

  日期：1998.7

  Lithiated oxazolo[3,4-a]benzimidazole 4 reacted with various alkyl halides to give oxazolo[3,4-a]benzimidazoles 5a-d in good yields as single diastereoisomers. (R)-Benzimidazol-2-y1 carbinols 6a-d were obtained upon hydrolysis under acidic conditions of 1H,3H-oxazolo[3,4-a]benzimidazole derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.