(+/-)-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalene-1-acetic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalene-1-acetic acid
• 英文别名: 2-(7-oxo-2,3,4,4a,5,6-hexahydro-1H-naphthalen-1-yl)acetic acid
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: DZHQCSSDJOZTQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (7-Oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl)-acetic acid ethyl ester 生成 (+/-)-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalene-1-acetic acid
  参考文献：
  名称：

  (±)-7-Oxo-1,2,3,4,4a,5,6,7-octahydronaphthalene-1-acetic acid: catemeric hydrogen bonding and diastereomeric disorder in a bicyclic unsaturated ∊-keto acid

  摘要：

  The 68.5: 31.5 mixture of diastereoisomers obtained in the synthesis of the title compound, C12H16O3, yielded sharply melting crystals containing the same ratio of epimers, in a disordered crystallographic arrangement. The disorder resides almost entirely in the carboxymethyl side chain, but places the two sets of carboxyl O atoms at nearly identical paired spatial positions. Neither component displays significant carboxyl disorder, and the molecules aggregate as hydrogen-bonded carboxyl-to-ketone catemers [O...O = 2.673 (4) Angstrom and O-H...O = 158 degrees] having glide-related components, with centrosymmetrically related pairs of chains following axes perpendicular to b. Close intermolecular C - H...O contacts exist for both the ketone and the carboxyl group. The energetics of the epimers and of their crystallization mode are discussed.

  DOI：

  10.1107/s0108270104003075