isopropylidene glycerol 3-carboxy-2-naphthoate | 405140-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: isopropylidene glycerol 3-carboxy-2-naphthoate
• 英文别名: 3-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxycarbonyl]naphthalene-2-carboxylic acid
• CAS: 405140-48-9
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: MLENOSGNSKDFJA-UHFFFAOYSA-N

物化性质

• 沸点：
  489.9±35.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

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：

  (S)-(-)- α-甲基苄胺 、 isopropylidene glycerol 3-carboxy-2-naphthoate 以 乙醚 为溶剂， 生成 (S)-isopropylidene glycerol 3-carboxy-2-naphthoate (S)-1-phenylethylamine salt 、 (R)-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：

  2，3-萘二酐 、 丙酮缩甘油 以 吡啶 为溶剂， 反应 1.0h， 以100%的产率得到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

文献信息

• [EN] THIOPHENE DERIVATIVES, THEIR MANUFACTURE AND USE AS PHARMACEUTICAL AGENTS<br/>[FR] DERIVES DE THIOPHENE, LEUR FABRICATION ET LEUR UTILISATION COMME AGENTS PHARMACEUTIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005121134A1

  公开（公告）日：2005-12-22

  Objects of the present invention are the compounds of formula (I), their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.

  本发明的对象是公式（I）化合物，它们的药用盐、对映体形式、二对映异构体和拉克酸盐，上述化合物的制备，含有它们的药物以及其制造，以及上述化合物在控制或预防癌症等疾病中的应用。
• [EN] THIOPHENE HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS HDAC INHIBITORS<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE THIOPHENE ET LEUR UTILISATION COMME INHIBITEURS HDAC
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005121120A1

  公开（公告）日：2005-12-22

  Objects of the present invention are the compounds of formula (I) their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.

  本发明的对象是式（I）的化合物及其药学上可接受的盐、对映体形式、非对映异构体和消旋体，上述化合物的制备，含有它们的药物以及其制造，以及上述化合物在控制或预防癌症等疾病中的应用。
• Thiophene Derivatives, Their Manufacture and Use as Pharmaceutical Agents
  申请人：Fertig Georg

  公开号：US20070232602A1

  公开（公告）日：2007-10-04

  Objects of the present invention are the compounds of formula (I), their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.

  本发明的对象是公式（I）的化合物，它们的药学上可接受的盐，对映体形式，非对映异构体和混合物，上述化合物的制备，含有它们的药物以及它们的制造，以及上述化合物在控制或预防癌症等疾病中的使用。
• Thiophene Hydroxamic Acid Derivatives and Their Use as Hdac Inhibitors
  申请人：Fertig Georg

  公开号：US20080070976A1

  公开（公告）日：2008-03-20

  Objects of the present invention are the compounds of formula (I) their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.

  本发明的对象是公式(I)的化合物及其药学上可接受的盐、对映体、顺反异构体和混合物，上述化合物的制备，含有它们的药物以及其制造，以及上述化合物在控制或预防癌症等疾病中的应用。
• THIOPHENE HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS HDAC INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1758881A1

  公开（公告）日：2007-03-07