[(1S,2R,6S)-4-bromo-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl] 2-chloroacetate | 1190605-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1S,2R,6S)-4-bromo-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl] 2-chloroacetate
• CAS: 1190605-38-9
• 化学式: C₈H₆BrClO₄
• 分子量: 281.49
• InChiKey: ZRTNECKEHPWOQF-BTZDVCGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2R,6S)-4-bromo-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl] 2-chloroacetate 在 甲醇 、 zinc(II) acetate dihydrate 作用下， 反应 1.0h， 以88%的产率得到(-)-bromoxone
  参考文献：
  名称：

  Chemoenzymatic Access to Versatile Epoxyquinol Synthons

  摘要：

  The enantiomerically pure and readily available metabolites 10-12 have been converted over four simple steps into the epoxyquinol derivatives 22-24, respectively. Compounds 23 and 24 or their immediate precursors have been exploited in efficient total syntheses of (-)-bromoxone (ent-1), (-)-epiepoformin (ent-2), (-)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).

  DOI：

  10.1021/ol9016657
• 作为产物：
  描述：

  (1S,2R,5S,6R)-4-bromo-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-yl 2-chloroacetate 在 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到[(1S,2R,6S)-4-bromo-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl] 2-chloroacetate
  参考文献：
  名称：

  Chemoenzymatic Access to Versatile Epoxyquinol Synthons

  摘要：

  The enantiomerically pure and readily available metabolites 10-12 have been converted over four simple steps into the epoxyquinol derivatives 22-24, respectively. Compounds 23 and 24 or their immediate precursors have been exploited in efficient total syntheses of (-)-bromoxone (ent-1), (-)-epiepoformin (ent-2), (-)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).

  DOI：

  10.1021/ol9016657

文献信息

• Chemoenzymatic Access to Versatile Epoxyquinol Synthons
  作者：David M. Pinkerton、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/ol9016657

  日期：2009.10.1

  The enantiomerically pure and readily available metabolites 10-12 have been converted over four simple steps into the epoxyquinol derivatives 22-24, respectively. Compounds 23 and 24 or their immediate precursors have been exploited in efficient total syntheses of (-)-bromoxone (ent-1), (-)-epiepoformin (ent-2), (-)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).