(1R,2S,3S,4S)-3-Carbamoyl-2-carboxybicyclo<2.2.1>heptane | 132674-10-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,3S,4S)-3-Carbamoyl-2-carboxybicyclo<2.2.1>heptane
• 英文别名: (1R,2S,3S,4S)-3-carbamoylbicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 132674-10-3
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: PJARUKXCFRFPOP-VZFHVOOUSA-N

物化性质

• 沸点：
  451.3±24.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S)-3-Carbamoyl-2-carboxybicyclo<2.2.1>heptane 、 苯磺酰氯 在 sodium hydroxide 、 sodium hypochlorite 作用下， 生成 (1S,2S,3S,4R)-3-Carboxy-2-((phenylsulfonyl)amino)bicyclo<2.2.1>heptane
  参考文献：
  名称：

  Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist

  摘要：

  An efficient and extremely practical enantioselective fission of pro-chiral bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride was applied to the asymmetric synthesis of the potent and orally active thromboxane A2 (TXA2) receptor antagonist, S-1452. The lithium salt of (R)-(-)-benzylmandelate was employed as a chiral ligand, giving a crystalline key intermediate 3 of which the chemical purity was 100.0% after crystallization. Epimerization and the methanolysis process of 3 afforded the half ester 4, which was transformed into S-1452.

  DOI：

  10.1021/jo00006a030
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 盐酸 、 氢氧化钾 、 ammonium hydroxide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.2h， 生成 (1R,2S,3S,4S)-3-Carbamoyl-2-carboxybicyclo<2.2.1>heptane
  参考文献：
  名称：

  Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist

  摘要：

  An efficient and extremely practical enantioselective fission of pro-chiral bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride was applied to the asymmetric synthesis of the potent and orally active thromboxane A2 (TXA2) receptor antagonist, S-1452. The lithium salt of (R)-(-)-benzylmandelate was employed as a chiral ligand, giving a crystalline key intermediate 3 of which the chemical purity was 100.0% after crystallization. Epimerization and the methanolysis process of 3 afforded the half ester 4, which was transformed into S-1452.

  DOI：

  10.1021/jo00006a030

文献信息

• Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist
  作者：Mitsuaki Ohtani、Takaharu Matsuura、Fumihiko Watanabe、Masayuki Narisada

  DOI：10.1021/jo00006a030

  日期：1991.3

  An efficient and extremely practical enantioselective fission of pro-chiral bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride was applied to the asymmetric synthesis of the potent and orally active thromboxane A2 (TXA2) receptor antagonist, S-1452. The lithium salt of (R)-(-)-benzylmandelate was employed as a chiral ligand, giving a crystalline key intermediate 3 of which the chemical purity was 100.0% after crystallization. Epimerization and the methanolysis process of 3 afforded the half ester 4, which was transformed into S-1452.