(S)-isopropylidene glycerol 3-carboxy-2-naphthoate | 405140-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-isopropylidene glycerol 3-carboxy-2-naphthoate
• 英文别名: 3-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxycarbonyl]naphthalene-2-carboxylic acid
• CAS: 405140-50-3
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: MLENOSGNSKDFJA-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-苯乙胺 、 (S)-isopropylidene glycerol 3-carboxy-2-naphthoate 以 甲醇 为溶剂， 反应 0.08h， 以90%的产率得到(S)-isopropylidene glycerol 3-carboxy-2-naphthoate (S)-1-phenylethylamine salt
  参考文献：
  名称：

  Reciprocal resolutions between 1-phenylethylamine and carboxyesters of isopropylidene glycerol: improvement of the method by replacing mono-phthalate with 3-carboxy-2-naphthoate

  摘要：

  A novel resolving agent, isopropylidene glycerol 3-carboxy-2-naphthoate 2, was designed on the basis of the consideration that replacement of phenyl group with a naphthyl group would improve the resolving ability of isopropylidene glycerol hydrogen phthalate 1 while also conferring more suitable physicochemical properties for such a specific use. Indeed, 1-phenylethylamine 4 was resolved by 2 more efficiently than by I (respective resolution efficiencies, (S) 0.88 and 0.81), while 1 and 2 were resolved by 4 with S ranging between 0.54 and 0.59. Furthermore, 2 is a solid, whereas 1 is a viscous oil, and its recovery at the end of the resolution procedure is easier than that of 1. In order to understand the chiral discrimination mechanism of the two reciprocal resolutions, the binary melting point phase diagrams of the four diastereomeric systems (S)-2.(S)-4/(S)-2.(R)-4, (S)-2.(S)-4/(R)-2.(S)-4, (S)-1.(S)-4/(S)-1.(R)-4 and (S)-1.(S)-4/(R)-1.(S)-4 were determined. The first two systems form ideal conglomerates, characterised by identical diagrams, in which the eutectic corresponds to a 0.10 molar ratio of (S)-2-(S)-4. The same behaviour was shown by the other two systems, whose eutectics, however, correspond to a 0.18 molar ratio of (S)-1.(S)-4. On the basis of the present results, which indicate an excellent resolution ability of 2 for 4, the application of this new acid to the resolution of other 1-arylalkylamines seems to have very good prospects, worthy of investigation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00439-6
• 作为产物：
  描述：

  (S)-isopropylidene glycerol 3-carboxy-2-naphthoate (S)-1-phenylethylamine salt 在 硫酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-isopropylidene glycerol 3-carboxy-2-naphthoate
  参考文献：
  名称：

  Reciprocal resolutions between 1-phenylethylamine and carboxyesters of isopropylidene glycerol: improvement of the method by replacing mono-phthalate with 3-carboxy-2-naphthoate

  摘要：

  A novel resolving agent, isopropylidene glycerol 3-carboxy-2-naphthoate 2, was designed on the basis of the consideration that replacement of phenyl group with a naphthyl group would improve the resolving ability of isopropylidene glycerol hydrogen phthalate 1 while also conferring more suitable physicochemical properties for such a specific use. Indeed, 1-phenylethylamine 4 was resolved by 2 more efficiently than by I (respective resolution efficiencies, (S) 0.88 and 0.81), while 1 and 2 were resolved by 4 with S ranging between 0.54 and 0.59. Furthermore, 2 is a solid, whereas 1 is a viscous oil, and its recovery at the end of the resolution procedure is easier than that of 1. In order to understand the chiral discrimination mechanism of the two reciprocal resolutions, the binary melting point phase diagrams of the four diastereomeric systems (S)-2.(S)-4/(S)-2.(R)-4, (S)-2.(S)-4/(R)-2.(S)-4, (S)-1.(S)-4/(S)-1.(R)-4 and (S)-1.(S)-4/(R)-1.(S)-4 were determined. The first two systems form ideal conglomerates, characterised by identical diagrams, in which the eutectic corresponds to a 0.10 molar ratio of (S)-2-(S)-4. The same behaviour was shown by the other two systems, whose eutectics, however, correspond to a 0.18 molar ratio of (S)-1.(S)-4. On the basis of the present results, which indicate an excellent resolution ability of 2 for 4, the application of this new acid to the resolution of other 1-arylalkylamines seems to have very good prospects, worthy of investigation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00439-6
• 作为试剂：
  描述：

  非那明 在 (S)-isopropylidene glycerol 3-carboxy-2-naphthoate 、 硫酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 右旋苯丙胺 、 左苯丙胺
  参考文献：
  名称：

  Highly efficient resolutions with isopropylidene glycerol 3-carboxy-2-naphthoate

  摘要：

  A number of chiral 1-arylethylamines and 1-alkylethylamines were resolved with the 3-carboxy-2-naphthoate of isopropylidene glycerol 2, previously reported to be an even more efficient resolving agent for 1-phenylethylamine than the corresponding hemiphthalate 1. The results obtained for the 1-arylethylamines confirm such a trend revealing impressive resolution ability, in particular, for 1-(4-bromophenyl)-, 1-(4-nitrophenyl)- and 1-(2-naphthyl)ethylamine, whose enantiomers were almost quantitatively separated with (S)-2 by a single precipitation of the less soluble (S,S) diastereomeric salt. Additionally, the success of the resolutions of 1-alkylethylamines (1-phenyl-2-propylamine, 1-cyclohexylethylamine and 2-butylamine), which could not be resolved with 1, indicates that the novel carboxy ester 2 has a wider range of application than 1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00608-0

文献信息

• Reciprocal resolutions between 1-phenylethylamine and carboxyesters of isopropylidene glycerol: improvement of the method by replacing mono-phthalate with 3-carboxy-2-naphthoate
  作者：Marco Pallavicini、Ermanno Valoti、Luigi Villa、Oreste Piccolo

  DOI：10.1016/s0957-4166(01)00439-6

  日期：2001.9

  A novel resolving agent, isopropylidene glycerol 3-carboxy-2-naphthoate 2, was designed on the basis of the consideration that replacement of phenyl group with a naphthyl group would improve the resolving ability of isopropylidene glycerol hydrogen phthalate 1 while also conferring more suitable physicochemical properties for such a specific use. Indeed, 1-phenylethylamine 4 was resolved by 2 more efficiently than by I (respective resolution efficiencies, (S) 0.88 and 0.81), while 1 and 2 were resolved by 4 with S ranging between 0.54 and 0.59. Furthermore, 2 is a solid, whereas 1 is a viscous oil, and its recovery at the end of the resolution procedure is easier than that of 1. In order to understand the chiral discrimination mechanism of the two reciprocal resolutions, the binary melting point phase diagrams of the four diastereomeric systems (S)-2.(S)-4/(S)-2.(R)-4, (S)-2.(S)-4/(R)-2.(S)-4, (S)-1.(S)-4/(S)-1.(R)-4 and (S)-1.(S)-4/(R)-1.(S)-4 were determined. The first two systems form ideal conglomerates, characterised by identical diagrams, in which the eutectic corresponds to a 0.10 molar ratio of (S)-2-(S)-4. The same behaviour was shown by the other two systems, whose eutectics, however, correspond to a 0.18 molar ratio of (S)-1.(S)-4. On the basis of the present results, which indicate an excellent resolution ability of 2 for 4, the application of this new acid to the resolution of other 1-arylalkylamines seems to have very good prospects, worthy of investigation. (C) 2001 Elsevier Science Ltd. All rights reserved.