(1S,2R,3R,6R)-6-amino-cyclohex-4-ene-2,3-isopropylidendioxy-1-ol | 959419-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R,6R)-6-amino-cyclohex-4-ene-2,3-isopropylidendioxy-1-ol
• 英文别名: (3aS,4S,5R,7aR)-5-amino-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 959419-40-0
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: UNGIXACDNAXZEY-OOJXKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,6R)-6-amino-cyclohex-4-ene-2,3-isopropylidendioxy-1-ol 在 Dowex-50 (H⁺ form) ammonium hydroxide 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、2.67 kPa 条件下， 以98%的产率得到(1S,2R,3R,6R)-6-amino-cyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Biological Evaluation of (−)‐Conduramine C‐4

  摘要：

  Previously unreported (-)-conduramine C-4 was synthesized in six steps from a bacterial bromobenzene metabolite in 23% overall yield. The chemoenzymatic route involved toluene dioxygenase dihydroxylation, beta-epoxidation, epoxide ring-opening, Staudinger reduction, radical debromination, and Amberlite- catalyzed hydrolysis. (-)-Conduramine C-4 and other related compounds synthesised were assayed for galactosidase-activity inhibition against (beta-D-galactoside galactohidrolase isolated from Aspergillus oryzae.

  DOI：

  10.1080/00397910701555725
• 作为产物：
  描述：

  (3aS,4S,5R,7aS)-5-Azido-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以31%的产率得到(1S,2R,3R,6R)-6-amino-cyclohex-4-ene-2,3-isopropylidendioxy-1-ol
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Biological Evaluation of (−)‐Conduramine C‐4

  摘要：

  Previously unreported (-)-conduramine C-4 was synthesized in six steps from a bacterial bromobenzene metabolite in 23% overall yield. The chemoenzymatic route involved toluene dioxygenase dihydroxylation, beta-epoxidation, epoxide ring-opening, Staudinger reduction, radical debromination, and Amberlite- catalyzed hydrolysis. (-)-Conduramine C-4 and other related compounds synthesised were assayed for galactosidase-activity inhibition against (beta-D-galactoside galactohidrolase isolated from Aspergillus oryzae.

  DOI：

  10.1080/00397910701555725

文献信息

• Chemoenzymatic Synthesis and Biological Evaluation of (−)‐Conduramine C‐4
  作者：Ana Bellomo、Cecilia Giacomini、Beatriz Brena、Gustavo Seoane、David Gonzalez

  DOI：10.1080/00397910701555725

  日期：2007.10.1

  Previously unreported (-)-conduramine C-4 was synthesized in six steps from a bacterial bromobenzene metabolite in 23% overall yield. The chemoenzymatic route involved toluene dioxygenase dihydroxylation, beta-epoxidation, epoxide ring-opening, Staudinger reduction, radical debromination, and Amberlite- catalyzed hydrolysis. (-)-Conduramine C-4 and other related compounds synthesised were assayed for galactosidase-activity inhibition against (beta-D-galactoside galactohidrolase isolated from Aspergillus oryzae.