methyl 8a-methyl-1-oxo-Δ^6,7-octalin-7-carboxylate | 142811-23-2

• 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: methyl 8a-methyl-1-oxo-Δ^6,7-octalin-7-carboxylate
• 英文别名: methyl (4aR,8aS)-8a-methyl-8-oxo-1,4,4a,5,6,7-hexahydronaphthalene-2-carboxylate
• CAS: 142811-23-2
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: IFSRRWXAQXPIMB-MFKMUULPSA-N

物化性质

• 沸点：
  319.9±35.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 8a-methyl-1-oxo-Δ^6,7-octalin-7-carboxylate 在 Rh/Al₂O₃ 吡啶 、 盐酸羟胺 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 methyl 8a-methyl-1-(hydroxyimino)octalin-7-carboxylate
  参考文献：
  名称：

  Design and synthesis of intramolecular ion-pairing cis-bicyclo[4.4.0]decane (cis-decalin) amino acids: conformation-based probes of electrostatic interactions in water

  摘要：

  The design strategy and synthesis of cis-bicyclo[4.4.0]decane (cis-decalin) derivatives as conformation-based probes of electrostatic interactions in H2O are described. The molecules were designed so that formation of an intramolecular electrostatic interaction occurs in only one of two low-energy conformers; hence, the conformational equilibrium of a given molecule is under control of the electrostatic interaction, which can be determined accurately with NMR studies. The structural definition inherent to the molecules will enable the thermodynamics and kinetics of solvent reorganization, which controls formation of electrostatic interactions in H2O, to be probed directly. The first probe, a cis-decalin amino acid designed to evaluate an intramolecular ion pair, has been synthesized. The total synthesis was efficient and illustrated many of the strategies and potential pitfalls associated with the preparation of conformationally flexible ring systems. In particular, the inherent facial selectivity afforded by the shape of the cis-decalin, a critical component of the synthetic design, was reversed in one step in which hydrogen was added from the sterically encumbered concave face of the molecule. A cis-decalin amino acid of a different stereoelectronic array was also prepared. These molecules are the first examples to emerge from the application of a general design and synthetic strategy that will enable probes for all of the important biological electrostatic interactions to be constructed. The study of these molecules will provide significant insight into the synergistic role of molecular structure and solvent at controlling electrostatic interactions in H2O, an important basis of biological structure and function.

  DOI：

  10.1021/jo00042a015
• 作为产物：
  描述：

  methyl 1,1-<(2,2-dimethylpropane-1,3-diyl)dioxy>-6-oxo-8a-methyl-Δ^4a,5-octalin-7-carboxylate 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 138.5h， 生成 methyl 8a-methyl-1-oxo-Δ^6,7-octalin-7-carboxylate
  参考文献：
  名称：

  Design and synthesis of intramolecular ion-pairing cis-bicyclo[4.4.0]decane (cis-decalin) amino acids: conformation-based probes of electrostatic interactions in water

  摘要：

  The design strategy and synthesis of cis-bicyclo[4.4.0]decane (cis-decalin) derivatives as conformation-based probes of electrostatic interactions in H2O are described. The molecules were designed so that formation of an intramolecular electrostatic interaction occurs in only one of two low-energy conformers; hence, the conformational equilibrium of a given molecule is under control of the electrostatic interaction, which can be determined accurately with NMR studies. The structural definition inherent to the molecules will enable the thermodynamics and kinetics of solvent reorganization, which controls formation of electrostatic interactions in H2O, to be probed directly. The first probe, a cis-decalin amino acid designed to evaluate an intramolecular ion pair, has been synthesized. The total synthesis was efficient and illustrated many of the strategies and potential pitfalls associated with the preparation of conformationally flexible ring systems. In particular, the inherent facial selectivity afforded by the shape of the cis-decalin, a critical component of the synthetic design, was reversed in one step in which hydrogen was added from the sterically encumbered concave face of the molecule. A cis-decalin amino acid of a different stereoelectronic array was also prepared. These molecules are the first examples to emerge from the application of a general design and synthetic strategy that will enable probes for all of the important biological electrostatic interactions to be constructed. The study of these molecules will provide significant insight into the synergistic role of molecular structure and solvent at controlling electrostatic interactions in H2O, an important basis of biological structure and function.

  DOI：

  10.1021/jo00042a015

文献信息

• Design and synthesis of intramolecular ion-pairing cis-bicyclo[4.4.0]decane (cis-decalin) amino acids: conformation-based probes of electrostatic interactions in water
  作者：Craig Beeson、Thomas A. Dix

  DOI：10.1021/jo00042a015

  日期：1992.7

  The design strategy and synthesis of cis-bicyclo[4.4.0]decane (cis-decalin) derivatives as conformation-based probes of electrostatic interactions in H2O are described. The molecules were designed so that formation of an intramolecular electrostatic interaction occurs in only one of two low-energy conformers; hence, the conformational equilibrium of a given molecule is under control of the electrostatic interaction, which can be determined accurately with NMR studies. The structural definition inherent to the molecules will enable the thermodynamics and kinetics of solvent reorganization, which controls formation of electrostatic interactions in H2O, to be probed directly. The first probe, a cis-decalin amino acid designed to evaluate an intramolecular ion pair, has been synthesized. The total synthesis was efficient and illustrated many of the strategies and potential pitfalls associated with the preparation of conformationally flexible ring systems. In particular, the inherent facial selectivity afforded by the shape of the cis-decalin, a critical component of the synthetic design, was reversed in one step in which hydrogen was added from the sterically encumbered concave face of the molecule. A cis-decalin amino acid of a different stereoelectronic array was also prepared. These molecules are the first examples to emerge from the application of a general design and synthetic strategy that will enable probes for all of the important biological electrostatic interactions to be constructed. The study of these molecules will provide significant insight into the synergistic role of molecular structure and solvent at controlling electrostatic interactions in H2O, an important basis of biological structure and function.