5-(Hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-one | 177089-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(Hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-one
• CAS: 177089-30-4
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: BWULFBGZLLWXPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 5-(Hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-one 在 Candida antarctica lipase 作用下， 以 异丙醚 为溶剂， 反应 20.0h， 生成 (5S)-5-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-one 、 (5R)-5-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-one 、 [(4S)-2,2,4-trimethyl-5-oxo-1,3-dioxolan-4-yl]methyl acetate 、 [(4R)-2,2,4-trimethyl-5-oxo-1,3-dioxolan-4-yl]methyl acetate
  参考文献：
  名称：

  Synthesis and Lipase-Catalyzed Resolution of 5-(Hydroxymethyl)-1,3-dioxolan-4-ones:  Masked Glycerol Analogs as Potential Building Blocks for Pharmaceuticals

  摘要：

  (Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were alpha-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential beta-blocking activity.

  DOI：

  10.1021/jo952021v
• 作为产物：
  描述：

  2,2,5-trimethyl-1,3-dioxolan-4-one 在 palladium on activated charcoal 正丁基锂 、 氢气 、 二异丙胺 作用下， 以 乙醇 为溶剂， 反应 48.25h， 生成 5-(Hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Synthesis and Lipase-Catalyzed Resolution of 5-(Hydroxymethyl)-1,3-dioxolan-4-ones:  Masked Glycerol Analogs as Potential Building Blocks for Pharmaceuticals

  摘要：

  (Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were alpha-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential beta-blocking activity.

  DOI：

  10.1021/jo952021v