(1R,2S,3R,4S)-2-<(R)-Mandeloxycarbonyl>-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid | 130362-19-5

• 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: (1R,2S,3R,4S)-2-<(R)-Mandeloxycarbonyl>-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid
• 英文别名: (1R,2S,3R,4S)-2-((R)-Mandeloxycarbonyl)-7-oxabicyclo[2.2.1]heptane-3-carboxylic Acid；(1S,2R,3S,4R)-3-[(R)-carboxy(phenyl)methoxy]carbonyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 130362-19-5
• 化学式: C₁₆H₁₆O₇
• 分子量: 320.299
• InChiKey: DITDKWNVICCXGD-OBPIAQAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-2-<(R)-Mandeloxycarbonyl>-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 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 、 norcantharidin 生成 (1R,2S,3R,4S)-2-<(R)-Mandeloxycarbonyl>-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

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.