1-(2,6-Dimethylphenoxy)-2-methansulfonyloxy-propan | 68164-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2,6-Dimethylphenoxy)-2-methansulfonyloxy-propan
• 英文别名: 1-(2,6-Dimethylphenoxy)propan-2-yl methanesulfonate
• CAS: 68164-74-9
• 化学式: C₁₂H₁₈O₄S
• 分子量: 258.339
• InChiKey: NWINJJIRFPNRDA-UHFFFAOYSA-N

物化性质

• 沸点：
  402.8±33.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,6-Dimethylphenoxy)-2-methansulfonyloxy-propan 在 镍 sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 美西律
  参考文献：
  名称：

  Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine)

  摘要：

  Mexiletine [1-(2,6-dimethylphenoxy)-2-aminopropane], an orally effective antiarrhythmic agent, exhibits enantioselective pharmacokinetics and pharmacodynamics during mexiletine therapy. The purpose of this paper is to emphasize the advantage of tetrahydropyranyl-protected mandelic acid (THPMA) in the resolution of mexiletine enantiomers. Both enantiomers of mexiletine were obtained in 99% enantiomeric excess. Judging by the differential shielding effects in the H-1 and C-13 NMR analyses, we have observed the opposite predominant conformation for the mexiletine mandelates in comparison with the O-methylmandelates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00311-0
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 1-(2,6-Dimethylphenoxy)-2-methansulfonyloxy-propan
  参考文献：
  名称：

  Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine)

  摘要：

  Mexiletine [1-(2,6-dimethylphenoxy)-2-aminopropane], an orally effective antiarrhythmic agent, exhibits enantioselective pharmacokinetics and pharmacodynamics during mexiletine therapy. The purpose of this paper is to emphasize the advantage of tetrahydropyranyl-protected mandelic acid (THPMA) in the resolution of mexiletine enantiomers. Both enantiomers of mexiletine were obtained in 99% enantiomeric excess. Judging by the differential shielding effects in the H-1 and C-13 NMR analyses, we have observed the opposite predominant conformation for the mexiletine mandelates in comparison with the O-methylmandelates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00311-0

文献信息

• HESEK, D.;TEGZA, M.;RYBAR, A.;MARTVON, A.;KOSALKO, R.
  作者：HESEK, D.、TEGZA, M.、RYBAR, A.、MARTVON, A.、KOSALKO, R.

  DOI：——

  日期：——
• Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine)
  作者：Riina Aav、Omar Parve、Tõnis Pehk、Alf Claesson、Ivar Martin

  DOI：10.1016/s0957-4166(99)00311-0

  日期：1999.7

  Mexiletine [1-(2,6-dimethylphenoxy)-2-aminopropane], an orally effective antiarrhythmic agent, exhibits enantioselective pharmacokinetics and pharmacodynamics during mexiletine therapy. The purpose of this paper is to emphasize the advantage of tetrahydropyranyl-protected mandelic acid (THPMA) in the resolution of mexiletine enantiomers. Both enantiomers of mexiletine were obtained in 99% enantiomeric excess. Judging by the differential shielding effects in the H-1 and C-13 NMR analyses, we have observed the opposite predominant conformation for the mexiletine mandelates in comparison with the O-methylmandelates. (C) 1999 Elsevier Science Ltd. All rights reserved.