(2S)-3-tolyloxy-1,2-propanediol acetonide | 52094-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-3-tolyloxy-1,2-propanediol acetonide
• 英文别名: (2S)-3-o-Tolyloxy-1,2-propandiol-acetonid；(4S)-2,2-dimethyl-4-[(2-methylphenoxy)methyl]-1,3-dioxolane
• CAS: 52094-01-6
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: VWYJFDMNXJTNQS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-3-tolyloxy-1,2-propanediol acetonide 在 盐酸 作用下， 生成 (R)-(+)-3-(2-methylphenoxy)propane-1,2-diol
  参考文献：
  名称：

  3-芳氧基丙烷-1，2-二醇及其衍生物的绝对构型：美信素异构体

  摘要：

  由2 R-和2 S -3-甲苯磺酰氧基丙烷-1,2-二醇丙酮化物与邻甲酚（NaOH）反应制得美芬素（3-邻甲苯基丙烷-1,2-二醇）的旋光异构体根据Cupra A解决方案中的cd光谱确定。

  DOI：

  10.1039/c39730000896
• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 、 邻甲酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2S)-3-tolyloxy-1,2-propanediol acetonide
  参考文献：
  名称：

  Cardiovascular hybrid drugs: new benzazepinone derivatives as bradycardic agents endowed with selective β 1 -Non-competitive antagonism

  摘要：

  The synthesis and pharmacological profile of some hybrid compounds bearing both the benzazepinone moiety present in Zatebradine and typical P-blocker aryloxypropanolamine groups are described. The new compounds proved to be endowed with negative chronotropic and inotropic activity and are weak vasorelaxant agents. The cardiodepressant action is probably due to selective beta(1)-noncompetitive reversible antagonism. Both enantiomers of the most active compound 5c were synthesized and they showed a different cardiovascular profile, that is (+)-(R)-enantiomer displays affinity for cardiac beta(1)-adrenoceptors, while (-)-(S)-enantiomer shows specificity for vessel smooth muscle. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00621-1

文献信息

• Absolute configuration of glycerol derivatives. 3. Synthesis and Cupra A circular dichroism spectra of some chiral 3-aryloxy-1,2-propanediols and 3-aryloxy-1-amino-2-propanols
  作者：Wendel L. Nelson、John E. Wennerstrom、S. Raman Sankar

  DOI：10.1021/jo00426a016

  日期：1977.3
• Cardiovascular hybrid drugs: new benzazepinone derivatives as bradycardic agents endowed with selective β 1 -Non-competitive antagonism
  作者：Alessandra Bisi、Angela Rampa、Roberta Budriesi、Silvia Gobbi、Federica Belluti、Pierfranco Ioan、Ermanno Valoti、Alberto Chiarini、Piero Valenti

  DOI：10.1016/s0968-0896(02)00621-1

  日期：2003.4

  The synthesis and pharmacological profile of some hybrid compounds bearing both the benzazepinone moiety present in Zatebradine and typical P-blocker aryloxypropanolamine groups are described. The new compounds proved to be endowed with negative chronotropic and inotropic activity and are weak vasorelaxant agents. The cardiodepressant action is probably due to selective beta(1)-noncompetitive reversible antagonism. Both enantiomers of the most active compound 5c were synthesized and they showed a different cardiovascular profile, that is (+)-(R)-enantiomer displays affinity for cardiac beta(1)-adrenoceptors, while (-)-(S)-enantiomer shows specificity for vessel smooth muscle. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Absolute configuration of 3-aryloxypropane-1,2-diols and derivatives: mephenesin isomers
  作者：Wendel L. Nelson、Carl E. Wood

  DOI：10.1039/c39730000896

  日期：——

  The optical isomers of mephenesin (3-o-tolylpropane-1,2-diol) were prepared from 2R- and 2S-3-tosyloxypropane-1,2-diol acetonide by reaction with o-cresol(NaOH) and the configurations confirmed on the basis of c.d. spectra in Cupra A Solution.

  由2 R-和2 S -3-甲苯磺酰氧基丙烷-1,2-二醇丙酮化物与邻甲酚（NaOH）反应制得美芬素（3-邻甲苯基丙烷-1,2-二醇）的旋光异构体根据Cupra A解决方案中的cd光谱确定。