1,2-Propanediol, 3-(o-tolyloxy)-, diacetate | 63991-86-6

• 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-Propanediol, 3-(o-tolyloxy)-, diacetate
• 英文别名: Acetic acid (S)-1-acetoxymethyl-2-o-tolyloxy-ethyl ester
• CAS: 63991-86-6；138710-06-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: CVMSKRHCTWCITE-ZDUSSCGKSA-N

物化性质

• 沸点：
  377.2±32.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 甲酚甘油醚 在 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 60.0h， 生成 1-acetoxy-3-(2-methylphenoxy)propan-2-ol 、 1,2-Propanediol, 3-(o-tolyloxy)-, diacetate 、 Acetic acid (S)-1-acetoxymethyl-2-o-tolyloxy-ethyl ester
  参考文献：
  名称：

  Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents

  摘要：

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.

  DOI：

  10.1021/jo00081a018

文献信息

• Kinetic resolution of rac-3-(2-methylphenoxy)propane-1,2-diol (mephenesin) by sequential lipase-catalyzed transesterification
  作者：Fritz Theil、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/s0957-4166(00)86153-4

  日期：1991.1

  The kinetic resolution of rac-3-(2-methylphenoxy)propane-1,2-diol (rac-1, Mephenesin) by sequential lipase-catalyzed transesterification with vinyl acetate in tetrahydrofuran/triethylamine in the presence of lipase Amano PS is described.