(1R,2R,3R,4S)-2-(Methoxycarbonyl)-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid | 130464-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R,3R,4S)-2-(Methoxycarbonyl)-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid
• 英文别名: (1R,2R,3R,4S)-2-(Methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-3-carboxylic Acid；(1S,2R,3R,4R)-3-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 130464-50-5
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: RTYHOZSKZMLUKB-VZFHVOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  norcantharidin 以 甲醇 为溶剂， 生成 (1R,2R,3R,4S)-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

文献信息

• OHTANI, MITSUAKI;MATSUURA, TAKAHARU;WATANABE, FUMIHIKO;NARISADA, MASAYUKI, J. ORG. CHEM., 56,(1991) N3, C. 4120-4123
  作者：OHTANI, MITSUAKI、MATSUURA, TAKAHARU、WATANABE, FUMIHIKO、NARISADA, MASAYUKI

  DOI：——

  日期：——
• 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.