(R)-Hydroxymethylmexiletine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-Hydroxymethylmexiletine
• 英文别名: (-)-(R)-[2-(2-aminopropoxy)-3-methylphenyl]methanol；[2-[(2R)-2-aminopropoxy]-3-methylphenyl]methanol
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: XMJYSMLLWRQQAE-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

(R)-(-)-Mexiletine, 2-羟基-羟甲基是已知的人类代谢物。

(R)-(-)-Mexiletine, 2-hydroxy-hydroxymethyl is a known human metabolite of (R)-(-)-Mexiletine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  (-)-(R)-2-{2-[2-(hydroxymethyl)-6-methylphenoxy]-1-methylethyl}-1H-isoindole-1,3(2H)-dione 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以97%的产率得到(R)-Hydroxymethylmexiletine
  参考文献：
  名称：

  Synthesis of (R)-, (S)-, and (RS)-hydroxymethylmexiletine, one of the major metabolites of mexiletine

  摘要：

  Hydroxymethylmexiletine (HMM), one of the main metabolites of mexiletine, has been synthesized in both racemic and optically active forms following two alternative routes. The ee values for both HMM enantiomers were 98%, as assessed by H-1 NMR analysis in the presence of (-)-(R)-(2-naphthyloxy) phenylacetic acid as a chiral solvating agent and electrophoretic analysis using beta-cyclodextrine sulfated sodium salt as a chiral auxiliary. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.002

文献信息

• Synthesis of (R)-, (S)-, and (RS)-hydroxymethylmexiletine, one of the major metabolites of mexiletine
  作者：Maria Maddalena Cavalluzzi、Alessia Catalano、Claudio Bruno、Angelo Lovece、Alessia Carocci、Filomena Corbo、Carlo Franchini、Giovanni Lentini、Vincenzo Tortorella

  DOI：10.1016/j.tetasy.2007.10.002

  日期：2007.10

  Hydroxymethylmexiletine (HMM), one of the main metabolites of mexiletine, has been synthesized in both racemic and optically active forms following two alternative routes. The ee values for both HMM enantiomers were 98%, as assessed by H-1 NMR analysis in the presence of (-)-(R)-(2-naphthyloxy) phenylacetic acid as a chiral solvating agent and electrophoretic analysis using beta-cyclodextrine sulfated sodium salt as a chiral auxiliary. (c) 2007 Elsevier Ltd. All rights reserved.