(R)-ethopropazine hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (R)-ethopropazine hydrochloride
• 英文别名: (-)-ethopropazine hydrochloride；(2R)-N,N-diethyl-1-phenothiazin-10-ylpropan-2-amine;hydrochloride
• 化学式: C₁₉H₂₄N₂S*ClH
• 分子量: 348.94
• InChiKey: VXPCQISYVPFYRK-XFULWGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  31.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-ethopropazine (R,R)-O,O'-dibenzoyl-tartrate 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (R)-ethopropazine hydrochloride
  参考文献：
  名称：

  Separation, Conformation in Solution and Absolute Configuration of Ethopropazine Enantiomers

  摘要：

  Enantiomers of ethopropazine x HCl (10-(2-diethylaminopropyl)phenothiazine hydrochloride) were prepared by fractional crystallization of diastereomeric dibenzoyltartaric acid salts, and their optical purity (enantiomeric excess, ee) determined by HPLC on Chiralcel OJ column. With a solvent mixture n-hexane/t-butanol/triethylamine (100:3:0.5) as eluent a very good enantioseparation (alpha = 1.68) for racemic ethopropazine was obtained. Enantiomeric purity for (-)-enantiomer was 99.1% and for (+)-enantiomer 97.9%. Combined data from NMR and CD spectra of both enantiomers, along with previously reported X-ray structure analyses of racemic ethopropazine, revealed skewed conformation of tricyclic system in solution, and (S)-configuration on the stereogenic center for (-)-enantiomer, and (R)-configuration for (+)-enantiomer.

  DOI：

  10.1080/10242430212188

文献信息

• [EN] CONTROLLED RELEASE COMPOSITIONS AND METHODS FOR USING SAME<br/>[FR] COMPOSITIONS A LIBERATION PROGRESSIVE ET SON PROCEDE D'UTILISATION
  申请人：——

  公开号：WO2003105811A3

  公开（公告）日：2004-07-29
• Separation, Conformation in Solution and Absolute Configuration of Ethopropazine Enantiomers
  作者：Goran Šinko、Predrag Novak、Dinko Žiher、Vladimir Vinković、Vitomir Šunjić、Vera Simeon-Rudolf

  DOI：10.1080/10242430212188

  日期：2002.3

  Enantiomers of ethopropazine x HCl (10-(2-diethylaminopropyl)phenothiazine hydrochloride) were prepared by fractional crystallization of diastereomeric dibenzoyltartaric acid salts, and their optical purity (enantiomeric excess, ee) determined by HPLC on Chiralcel OJ column. With a solvent mixture n-hexane/t-butanol/triethylamine (100:3:0.5) as eluent a very good enantioseparation (alpha = 1.68) for racemic ethopropazine was obtained. Enantiomeric purity for (-)-enantiomer was 99.1% and for (+)-enantiomer 97.9%. Combined data from NMR and CD spectra of both enantiomers, along with previously reported X-ray structure analyses of racemic ethopropazine, revealed skewed conformation of tricyclic system in solution, and (S)-configuration on the stereogenic center for (-)-enantiomer, and (R)-configuration for (+)-enantiomer.