(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid furan-2-ylmethyl ester | 185334-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid furan-2-ylmethyl ester
• 英文别名: furan-2-ylmethyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 185334-27-4
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: KFRXHYCCGMIQPB-LSDHHAIUSA-N

物化性质

• 沸点：
  384.5±27.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid furan-2-ylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 98.5h， 生成 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,6S,7R)-3,5-dioxo-4,10-dioxa-tricyclo[5.2.1.02,6]dec-1-ylmethyl ester
  参考文献：
  名称：

  Synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]hept-2-enes precursors in the preparation of taxol analogues

  摘要：

  (S)-Camphanate of furfuryl alcohol undergoes Diels-Alder addition in molten maleic anhydride giving one major crystalline adduct (+)-2 ((1S,1S',2R,3S,4R)-1-[(camphanoyloxy)methyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride), the absolute configuration of which was established through chemical correlation. Adduct (+)-2 was converted into an enantiomerically pure intermediate as in Yadav's approach to the synthesis of taxol analogues. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00418-1
• 作为产物：
  描述：

  糠醇 、 (1S)-(-)-莰烷酰氯 在 吡啶 作用下， 以80%的产率得到(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid furan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]hept-2-enes precursors in the preparation of taxol analogues

  摘要：

  (S)-Camphanate of furfuryl alcohol undergoes Diels-Alder addition in molten maleic anhydride giving one major crystalline adduct (+)-2 ((1S,1S',2R,3S,4R)-1-[(camphanoyloxy)methyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride), the absolute configuration of which was established through chemical correlation. Adduct (+)-2 was converted into an enantiomerically pure intermediate as in Yadav's approach to the synthesis of taxol analogues. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00418-1

文献信息

• Synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]hept-2-enes precursors in the preparation of taxol analogues
  作者：Viviane Theurillat-Moritz、Pierre Vogel

  DOI：10.1016/0957-4166(96)00418-1

  日期：1996.11

  (S)-Camphanate of furfuryl alcohol undergoes Diels-Alder addition in molten maleic anhydride giving one major crystalline adduct (+)-2 ((1S,1S',2R,3S,4R)-1-[(camphanoyloxy)methyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride), the absolute configuration of which was established through chemical correlation. Adduct (+)-2 was converted into an enantiomerically pure intermediate as in Yadav's approach to the synthesis of taxol analogues. Copyright (C) 1996 Elsevier Science Ltd