(2S)-3-(3-methoxyphenoxy)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: (2S)-3-(3-methoxyphenoxy)propane-1,2-diol
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: PVXJBKOQPCPILX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(M-甲氧基苯氧基)-1,2-丙烷二醇 在 ion-exchange resin Wofatit SBW (OH(-)-form) 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 100.0h， 生成 (2S)-3-(3-methoxyphenoxy)propane-1,2-diol
  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

• Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers.³¹P NMR analysis of the enantiomeric composition of oxiranes
  作者：A. A. Bredikhin、E. I. Strunskaya、V. G. Novikova、N. M. Azancheev、D. R. Sharafutdinova、Z. A. Bredikhina

  DOI：10.1023/b:rucb.0000024851.29744.21

  日期：2004.1

  The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2-dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously

  研究了在手性 Co(salen) 催化剂存在下，许多外消旋芳基缩水甘油醚的对映选择性部分水解。分离的(R)-芳基缩水甘油醚的对映体组成通过31P NMR使用光学活性取代的2-氯-1,3,2-二氧杂环戊烷进行分析。提出了基于同时获得的 (S)-3-芳氧基丙烷-1,2-二醇合成 β-肾上腺素阻滞剂 (S)-toliprolol 和 (S)-moprolol。
• Reetz, Manfred T.; Bocola, Marco; Wang, Li-Wen, Journal of the American Chemical Society, 2009, vol. 131, p. 7334 - 7343
  作者：Reetz, Manfred T.、Bocola, Marco、Wang, Li-Wen、Sanchis, Joaquin、Cronin, Annette、et al.

  DOI：——

  日期：——
• Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00081a018

  日期：1994.1

  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.