(6R)-6,7-dihydro-5H-imidazo[1,5-a]azepine-6-ol | 935553-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (6R)-6,7-dihydro-5H-imidazo[1,5-a]azepine-6-ol
• 英文别名: (6R)-6,7-dihydro-5H-imidazo[1,5-a]azepin-6-ol
• CAS: 935553-98-3
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: ZCYYBSQABHAUSW-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6R)-6,7-dihydro-5H-imidazo[1,5-a]azepine-6-ol 在 potassium osmate(VI) 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (6R,8R,9S)-6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepin-6,8,9-triol 、 (6R,8S,9R)-6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepin-6,8,9-triol
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiomeric imidazolopiperidinoses and imidazoloazepanoses using Wittig/dihydroxylation reactions

  摘要：

  A new route for the synthesis of imidazolosugars-6-deoxyimidazolopiperidinoses 1 and 2 and 7-deoxyimidazoloazepanoses 3 and 4 in two enantiomerical forms-is reported. The new synthetic approach is based on two key reactions: (i) stereocontrolled Wittig Z-olefination of an imidazolecarbaldehyde with phosphoranes containing one chiral centre, obtained from (S)- and (R)-1,2,4-butantriol; (ii) diastereoselective cis-dihydroxylation of previously obtained olefins. All synthesised imidazolosugars were evaluated as potential inhibitors of glycosidases. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.016
• 作为产物：
  描述：

  (R)-(Z)-1-[1'-(triphenylmethyl)-1'H-imidazol-4'-yl]-4,5-O-isopropylidene-pent-1-en-4,5-diol 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 丙酮 为溶剂， 反应 30.0h， 生成 (6R)-6,7-dihydro-5H-imidazo[1,5-a]azepine-6-ol
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiomeric imidazolopiperidinoses and imidazoloazepanoses using Wittig/dihydroxylation reactions

  摘要：

  A new route for the synthesis of imidazolosugars-6-deoxyimidazolopiperidinoses 1 and 2 and 7-deoxyimidazoloazepanoses 3 and 4 in two enantiomerical forms-is reported. The new synthetic approach is based on two key reactions: (i) stereocontrolled Wittig Z-olefination of an imidazolecarbaldehyde with phosphoranes containing one chiral centre, obtained from (S)- and (R)-1,2,4-butantriol; (ii) diastereoselective cis-dihydroxylation of previously obtained olefins. All synthesised imidazolosugars were evaluated as potential inhibitors of glycosidases. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.016