(1S,2R,3S,4R)-2-<(R)-Mandeloxycarbonyl>bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid | 130362-18-4

• 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: (1S,2R,3S,4R)-2-<(R)-Mandeloxycarbonyl>bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid
• 英文别名: (1R,2S,3R,4S)-3-[(R)-carboxy(phenyl)methoxy]carbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS: 130362-18-4
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: XIUMXKCXAUISNO-MEBFFEOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100.9
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-2-<(R)-Mandeloxycarbonyl>bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid 、 sodium methylate 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到(1S,2S,3S,4R)-2-(Methoxycarbonyl)bicyclo<2.2.1>hept-5-ene-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：

  p-Methoxybenzyl (R)-(-)-mandelate 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 生成 (1S,2R,3S,4R)-2-<(R)-Mandeloxycarbonyl>bicyclo<2.2.1>hept-5-ene-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：——
• OHTANI, MITSUAKI;MATSUURA, TAKAHARU;WATANABE, FUMIHIKO;NARISADA, MASAYUKI, J. ORG. CHEM., 56,(1991) N, C. 2122-2127
  作者：OHTANI, MITSUAKI、MATSUURA, TAKAHARU、WATANABE, FUMIHIKO、NARISADA, MASAYUKI

  DOI：——

  日期：——