(S)-isopropylidene glycerol 2-carboxybenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-isopropylidene glycerol 2-carboxybenzoate
• 英文别名: (S)-2-(((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)carbonyl)benzoic acid；2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxycarbonyl]benzoic acid
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: PCLHPOXWGFYRRM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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 2-carboxybenzoate 以 甲醇 为溶剂， 以82%的产率得到(S)-isopropylidene glycerol 2-carboxybenzoate (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-{[(2,2-二甲基-1,3-二氧杂烷-4-基)甲氧基]羰基}苯甲酸 生成 (S)-isopropylidene glycerol 2-carboxybenzoate
  参考文献：
  名称：

  Isopropylidene glycerol hydrogen phthalate: a new resolving agent. Application to the resolution of 1-arylethylamines

  摘要：

  Hydrogen phthalates of (R)- and (S)-isopropylidene glycerol, obtainable from racemic isopropylidene glycerol by reaction with phthalic anhydride and successive resolution with (S)- and (R)-1-phenylethylamine or, alternatively, from (R)-and (S)-isopropylidene glycerol, were regarded as potential new resolving agents. A range of important 1-arylethylamines was selected to test their resolving capability In particular, trial resolutions were carried out using equivalent amounts of racemic amine and hydrogen phthalate of (R)isopropylidene glycerol. The salts of the S isomers selectively crystallized from methanol or 2-propanol allowing to recover the (S)-1-arylethylamines in high chemical and optical yields. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00117-6

文献信息

• [EN] SALTS OF LORCASERIN WITH OPTICALLY ACTIVE ACIDS<br/>[FR] SELS DE LORCASÉRINE DOTÉS D'ACIDES OPTIQUEMENT ACTIFS
  申请人：ARENA PHARM INC

  公开号：WO2012030938A1

  公开（公告）日：2012-03-08

  Salts of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine with optically active acids, and pharmaceutical compositions comprising them that are useful for, inter alia, weight management.

  含有光学活性酸的8-氯-1-甲基-2,3,4,5-四氢-1H-3-苯并哌啶盐，以及包括它们的药物组合物，可用于诸如体重管理等用途。
• 一种拆分剂氢邻苯二甲酸异亚丙基甘油酯的 合成方法
  申请人：上海予利生物科技股份有限公司

  公开号：CN105315255B

  公开（公告）日：2017-12-26

  本发明涉及一种拆分剂氢邻苯二甲酸异亚丙基甘油酯的合成方法，该方法以(S)‑(‑)‑4‑氯甲基‑2，2‑二甲基‑1，3‑二氧戊环或(R)‑(+)‑4‑氯甲基‑2，2‑二甲基‑1，3‑二氧戊环为原料，与邻苯二甲酸氢钾反应，得到S/R‑氢邻苯二甲酸异亚丙基甘油酯。与现有技术相比，本发明直接采用商业化的手性原料，一步法直接合成拆分剂氢邻苯二甲酸异亚丙基甘油酯，原料来源容易，价格便宜。
• SALTS OF LORCASERIN WITH OPTICALLY ACTIVE ACIDS
  申请人：Blackburn Anthony C.

  公开号：US20130310369A1

  公开（公告）日：2013-11-21

  Salts of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine with optically active acids, and pharmaceutical compositions comprising them that are useful for, inter alia, weight management.

  8-氯-1-甲基-2,3,4,5-四氢-1H-3-苯并嗪的盐，与手性酸混合制成的药物组合物，可用于体重管理等用途。
• US9248133B2
  申请人：——

  公开号：US9248133B2

  公开（公告）日：2016-02-02
• 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.