Acetic acid (3aR,4S,5R,6aS)-4-benzyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester | 42586-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (3aR,4S,5R,6aS)-4-benzyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• CAS: 42586-89-0
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: WEJBYJRVJLARFP-LVQVYYBASA-N

物化性质

• 沸点：
  450.4±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,4S,5R,6aS)-4-benzyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 11.0h， 以72%的产率得到(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one
  参考文献：
  名称：

  Prins reaction of 2-oxabicyclo[3.3.0]oct-6-en-3-one and related derivatives

  摘要：

  Reaction of formaldehyde with the title olefinic lactone in acetic acid affords diacetate of 1,3-diol (2a) as the main product in 50 - 60% yield via regioselective trans-addition. Less favourable results were obtained with related bicyclic derivatives.

  DOI：

  10.1016/s0040-4020(01)88339-3
• 作为产物：
  描述：

  Acetic acid (3aR,4S,5S,6S,6aR)-4-benzyloxymethyl-6-iodo-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 在 三正丁基氢锡 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以89%的产率得到Acetic acid (3aR,4S,5R,6aS)-4-benzyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
  参考文献：
  名称：

  Prins reaction of 2-oxabicyclo[3.3.0]oct-6-en-3-one and related derivatives

  摘要：

  Reaction of formaldehyde with the title olefinic lactone in acetic acid affords diacetate of 1,3-diol (2a) as the main product in 50 - 60% yield via regioselective trans-addition. Less favourable results were obtained with related bicyclic derivatives.

  DOI：

  10.1016/s0040-4020(01)88339-3