(R)-2-溴异戊酸二环己胺盐 | 578742-53-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-2-溴异戊酸二环己胺盐
• 英文名称: (R)-2-bromoisovaleric acid dicyclohexylamine salt
• 英文别名: (r)-2-Bromoisovaleric acid dicyclohexylamine salt；(2R)-2-bromo-3-methylbutanoic acid;N-cyclohexylcyclohexanamine
• CAS: 578742-53-7
• 化学式: C₅H₉BrO₂*C₁₂H₂₃N
• 分子量: 362.351
• InChiKey: AKQIKHVFFCVIKB-FZSMXKCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-(+)-2-溴-3-甲基丁酸 、 二环己胺 在 氮气 、 甲苯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以to obtain 4.84 g of a (R)-2-bromoisovaleric acid dicyclohexylamine salt (optical purity 99.4% ee, crystallization yield 81%, apparent purity 94.5%, impurity content 2-hydroxy isovaleric acid: 0.04%, bromine content: 3.02%)的产率得到(R)-2-溴异戊酸二环己胺盐
  参考文献：
  名称：

  Process for production of optically active 2-halogeno-carboxylic acids

  摘要：

  本发明提供了一种有效制备对制药等方面有用的光学活性2-卤代羧酸及其与胺类的盐的方法。具体而言，通过在水中存在亲水性有机溶剂和亚硝酸的情况下卤代光学活性氨基酸，保留其构型并通过去除副产物2-羟基溴代羧酸抑制其对映异构化；将所得的光学活性2-卤代羧酸转化为其与碱的盐，并去除有机相，然后再将光学活性2-卤代羧酸转移至有机溶剂相，去除水相，从而通过去除卤素组分获得光学活性2-卤代羧酸。此外，通过结晶方法可以获得与胺的高质量光学活性2-卤代羧酸盐，其中胺在半小时或更长时间内连续或分批加入，结晶溶剂由亲水性有机溶剂和亲油性有机溶剂组成。

  公开号：

  US20050176999A1

文献信息

• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 2-HALOGENO- CARBOXYLIC ACIDS
  申请人：KANEKA CORPORATION

  公开号：EP1481960A1

  公开（公告）日：2004-12-01

  The invention provides processes for producing efficiently optically active 2-halogenocarboxylic acids useful in the preparation of drugs or the like and salts thereof with amines. Specifically, an optically active 2-halogenocarboxylic acid is produced by halogenating an optically active amino acid in water in the presence of a hydrophobic organic solvent and nitrous acid with the configuration retained and with the racemization inhibited through the removal of 2-hydroxy- bromocarboxylic acid formed as a by-product; the obtained optically active 2-halogenocarboxylic acid is transferred to an aqueous phase by converting it into a salt thereof with a base, followed by the removal of the organic phase; and the optically active 2-halogenocarboxylic acid is transferred again to an organic solvent phase, followed by the removal of the aqueous phase, whereby an optically active 2-halogenocarboxylic acid is obtained through the removal of a halogen component. Further, a high-quality salt of an optically active 2-halogenocarboxylic acid with an amine can be obtained by a crystallization method wherein the amine is added over the period of 1/2 hour or longer either continuously or in portions and/or wherein the crystallization solvent consists of a hydrophobic organic solvent and a hydrophilic organic solvent.

  本发明提供了生产高效光学活性 2-卤代羧酸的工艺，这种 2-卤代羧酸可用于制备药物 或类似药物及其与胺的盐。具体地说，在疏水性有机溶剂和亚硝酸的存在下，通过在水中卤化光学活性氨基酸来生产光学活性 2-卤代羧酸，并保留其构型，通过去除副产物 2-羟基溴羧酸来抑制其外消旋化；将得到的具有光学活性的 2-卤代羧酸用碱转化为盐，转移到水相中，然后去除有机相；将具有光学活性的 2-卤代羧酸再次转移到有机溶剂相中，然后去除水相，这样就通过去除卤素成分得到了具有光学活性的 2-卤代羧酸。此外，光学活性 2-卤代羧酸与胺的高质量盐可通过结晶方法获得，其中胺的添加时间为 1/2 小时或更长，可连续添加或部分添加，以及/或结晶溶剂由疏水性有机溶剂和亲水性有机溶剂组成。
• US7473803B2
  申请人：——

  公开号：US7473803B2

  公开（公告）日：2009-01-06
• Process for production of optically active 2-halogeno-carboxylic acids
  申请人：Yamashita Koki

  公开号：US20050176999A1

  公开（公告）日：2005-08-11

  The invention provides processes for producing efficiently optically active 2-halogenocarboxylic acids useful in the preparation of drugs or the like and salts thereof with amines. Specifically an optically active 2-halogenocarboxylic acid is produced by halogenating an optically active amino acid in water in the presence of a hydrophobic organic solvent and nitrous acid with the configuration retained and with the racemization inhibited through the removal of 2-hydroxy-bromocarboxylic acid formed as a by-product; the obtained optically active 2-halogenocarboxylic acid is transferred to an aqueous phase by converting it into a salt thereof with a base, followed by the removal of the organic phase; and the optically active 2-halogenocarboxylic acid is transferred again to an organic solvent phase, followed by the removal of the aqueous phase, whereby an optically active 2-halogenocarboxylic acid is obtained through the removal of a halogen component. Further, a high-quality salt of an optically active 2-halogenocarboxylic acid with an amine can be obtained by a crystallization method wherein the amine is added over the period of ½ hour or longer either continuously or in portions and/or wherein the crystallization solvent consists of a hydrophobic organic solvent and a hydrophilic organic solvent.

  本发明提供了一种有效制备对制药等方面有用的光学活性2-卤代羧酸及其与胺类的盐的方法。具体而言，通过在水中存在亲水性有机溶剂和亚硝酸的情况下卤代光学活性氨基酸，保留其构型并通过去除副产物2-羟基溴代羧酸抑制其对映异构化；将所得的光学活性2-卤代羧酸转化为其与碱的盐，并去除有机相，然后再将光学活性2-卤代羧酸转移至有机溶剂相，去除水相，从而通过去除卤素组分获得光学活性2-卤代羧酸。此外，通过结晶方法可以获得与胺的高质量光学活性2-卤代羧酸盐，其中胺在半小时或更长时间内连续或分批加入，结晶溶剂由亲水性有机溶剂和亲油性有机溶剂组成。