3-(2,4-dimethyl-phenoxy)-propane-1,2-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2,4-dimethyl-phenoxy)-propane-1,2-diol
• 英文别名: 3-(2,4-Dimethyl-phenoxy)-propan-1,2-diol；3-(2,4-Xylyloxy)-1,2-propanediol；3-(2,4-dimethylphenoxy)propane-1,2-diol
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: IOPOAHOTRMUGNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 3-(2,4-dimethyl-phenoxy)-propane-1,2-diol 以 四氢呋喃 为溶剂， 反应 264.0h， 以39%的产率得到(S)-1,2-diacetoxy-3-(2,4-dimethylphenoxy)propane
  参考文献：
  名称：

  Lipase-catalysed resolution of 3-(aryloxy)-1,2-propanediol derivatives — Towards an improved active site model of Pseudomonas cepacia lipase (amano PS)

  摘要：

  A variety of 3-(aryloxy)-1,2-propanediol derivatives with different substituents on the aromatic ring or at the primary hydroxy group were used as substrates in a kinetic resolution by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia (Amano PS). Derivatives with substituents in the para-position of the aromatic ring were accepted as substrates and resolved with high enantioselectivity. The corresponding derivatives with substituents in the ortho-position were much worse substrates for lipase PS or even non-substrates if the substituent was sufficiently space-filling as found for the tert-butyl, phenyl, benzyl or benzoyl residue. Otherwise, if the primary hydroxy group was substituted by unbranched long-chain acyl residues very good substrates were resulting. In contrast, derivatives with sterically crowded residues at the primary hydroxy group such as the pivaloyl, tert-butyldimethylsilyl, methanesulfonyl, para-toluenesulfonyl or trityl groups were nonsubstrates for lipase PS.

  DOI：

  10.1016/0957-4166(95)00166-m
• 作为产物：
  描述：

  3-氯-1,2-丙二醇 、 2,4-二甲基苯酚 在 sodium hydroxide 作用下， 生成 3-(2,4-dimethyl-phenoxy)-propane-1,2-diol
  参考文献：
  名称：

  Muscle-paralyzing Compounds Related to Mephenesin

  摘要：

  DOI：

  10.1021/ja01128a019

文献信息

• Muscle-paralyzing Compounds Related to Mephenesin
  作者：B. J. Ludwig、W. A. West、W. E. Currie

  DOI：10.1021/ja01128a019

  日期：1952.4
• Lipase-catalysed resolution of 3-(aryloxy)-1,2-propanediol derivatives — Towards an improved active site model of Pseudomonas cepacia lipase (amano PS)
  作者：Fritz Theil、Karin Lemke、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/0957-4166(95)00166-m

  日期：1995.6

  A variety of 3-(aryloxy)-1,2-propanediol derivatives with different substituents on the aromatic ring or at the primary hydroxy group were used as substrates in a kinetic resolution by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia (Amano PS). Derivatives with substituents in the para-position of the aromatic ring were accepted as substrates and resolved with high enantioselectivity. The corresponding derivatives with substituents in the ortho-position were much worse substrates for lipase PS or even non-substrates if the substituent was sufficiently space-filling as found for the tert-butyl, phenyl, benzyl or benzoyl residue. Otherwise, if the primary hydroxy group was substituted by unbranched long-chain acyl residues very good substrates were resulting. In contrast, derivatives with sterically crowded residues at the primary hydroxy group such as the pivaloyl, tert-butyldimethylsilyl, methanesulfonyl, para-toluenesulfonyl or trityl groups were nonsubstrates for lipase PS.