3-O-[(1R)-2-methoxy-2-oxo-1-phenylethyl] 2-O-methyl (1S,2R,3S,4R)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate | 130362-20-8

• 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: 3-O-[(1R)-2-methoxy-2-oxo-1-phenylethyl] 2-O-methyl (1S,2R,3S,4R)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate
• CAS: 130362-20-8
• 化学式: C₁₈H₂₀O₇
• 分子量: 348.353
• InChiKey: QGVOHURAUFOLIM-XPABHHOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-[(1R)-2-methoxy-2-oxo-1-phenylethyl] 2-O-methyl (1S,2R,3S,4R)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (1S,2R,3S,4R)-2-(Methoxycarbonyl)-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid
  参考文献：
  名称：

  Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid

  摘要：

  An effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptane-2,3-dicarboxylic acid was developed by enantioselective fission of sigma-symmetrical cyclic anhydrides with chiral mandelic acid derivatives, followed by deprotection of the mandelate moiety, crystallization, and further modification. These half-esters are very attractive chiral building blocks for numerous natural products, and this new method makes possible their synthesis via common intermediates with high optical purity.

  DOI：

  10.1021/jo00013a009
• 作为产物：
  描述：

  扁桃酸苯酯 在 对甲苯磺酸 作用下， 生成 3-O-[(1R)-2-methoxy-2-oxo-1-phenylethyl] 2-O-methyl (1S,2R,3S,4R)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate
  参考文献：
  名称：

  Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid

  摘要：

  An effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptane-2,3-dicarboxylic acid was developed by enantioselective fission of sigma-symmetrical cyclic anhydrides with chiral mandelic acid derivatives, followed by deprotection of the mandelate moiety, crystallization, and further modification. These half-esters are very attractive chiral building blocks for numerous natural products, and this new method makes possible their synthesis via common intermediates with high optical purity.

  DOI：

  10.1021/jo00013a009

文献信息

• Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid
  作者：Mitsuaki Ohtani、Takaharu Matsuura、Fumihiko Watanabe、Masayuki Narisada

  DOI：10.1021/jo00013a009

  日期：1991.6

  An effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptane-2,3-dicarboxylic acid was developed by enantioselective fission of sigma-symmetrical cyclic anhydrides with chiral mandelic acid derivatives, followed by deprotection of the mandelate moiety, crystallization, and further modification. These half-esters are very attractive chiral building blocks for numerous natural products, and this new method makes possible their synthesis via common intermediates with high optical purity.