Acetic acid (S)-2-bromo-1-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester | 151426-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Acetic acid (S)-2-bromo-1-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester
• CAS: 151426-63-0
• 化学式: C₁₃H₁₉BrO₆
• 分子量: 351.194
• InChiKey: GQVXAQSLSNOTOB-BZNQNGANSA-N

物化性质

• 沸点：
  441.5±45.0 °C(predicted)
• 密度：
  1.487±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-2-bromo-1-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以31%的产率得到Acetic acid (3aR,4aR,5R,7aR,7bR)-7a-hydroxy-2,2,7-trimethyl-hexahydro-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-yl ester
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8
• 作为产物：
  描述：

  乙酸酐 、 1,2-O-Isopropylidene-3-C-vinyl-α-D-allofuranose 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 生成 Acetic acid (S)-2-bromo-1-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 、 Acetic acid (3aR,5R,6R,6aR)-5-((S)-1-acetoxy-2-bromo-ethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8