(4R,1'S)-dihydro-4-(1'-hydroxyethyl)-2(3H)-furanone | 851526-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,1'S)-dihydro-4-(1'-hydroxyethyl)-2(3H)-furanone
• 英文别名: (4R)-4-[(1S)-1-hydroxyethyl]oxolan-2-one
• CAS: 851526-25-5
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: SDQNMZALKPBELF-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (4R,1'S)-dihydro-4-(1'-hydroxyethyl)-2(3H)-furanone 在 4-二甲氨基吡啶 作用下， 以 1,4-二氧六环 为溶剂， 生成 (4R,1'S)-dihydro-4-(1-acetoxyethyl)-2(3H)-furanone
  参考文献：
  名称：

  A study of the enantiopreference of lipase PS (Pseudomonas cepacia) towards diastereomeric dihydro-5-alkyl-4-hydroxymethyl-2(3H)-furanones

  摘要：

  Lipase PS acetylation of diastereomeric dihydro-4-hydroxymethyl-2(3H)-furanones bearing a methyl or a pentyl group at C-5 have been studied. Higher enantioselectivities were found for the cis-isomers with respect to the trans-isomers. They were also higher for the systems bearing the longer alkyl chain. Lipase PS-catalyzed hydrolyses of racemic acetates were found to follow the same trend, although the efficiency of the enzyme was lower than in the acetylation reactions. These results were supported by molecular modelling studies that correctly predicted the maximum stereo selectivity for the cis-isomer of 5-pentyl substituted lactones both in acetylation and in hydrolysis reactions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.036
• 作为产物：
  描述：

  (-)-(2S,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 3.08h， 生成 (4R,1'S)-dihydro-4-(1'-hydroxyethyl)-2(3H)-furanone
  参考文献：
  名称：

  A study of the enantiopreference of lipase PS (Pseudomonas cepacia) towards diastereomeric dihydro-5-alkyl-4-hydroxymethyl-2(3H)-furanones

  摘要：

  Lipase PS acetylation of diastereomeric dihydro-4-hydroxymethyl-2(3H)-furanones bearing a methyl or a pentyl group at C-5 have been studied. Higher enantioselectivities were found for the cis-isomers with respect to the trans-isomers. They were also higher for the systems bearing the longer alkyl chain. Lipase PS-catalyzed hydrolyses of racemic acetates were found to follow the same trend, although the efficiency of the enzyme was lower than in the acetylation reactions. These results were supported by molecular modelling studies that correctly predicted the maximum stereo selectivity for the cis-isomer of 5-pentyl substituted lactones both in acetylation and in hydrolysis reactions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.036

文献信息

• A study of the enantiopreference of lipase PS (Pseudomonas cepacia) towards diastereomeric dihydro-5-alkyl-4-hydroxymethyl-2(3H)-furanones
  作者：Federico Berti、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2005.01.036

  日期：2005.3

  Lipase PS acetylation of diastereomeric dihydro-4-hydroxymethyl-2(3H)-furanones bearing a methyl or a pentyl group at C-5 have been studied. Higher enantioselectivities were found for the cis-isomers with respect to the trans-isomers. They were also higher for the systems bearing the longer alkyl chain. Lipase PS-catalyzed hydrolyses of racemic acetates were found to follow the same trend, although the efficiency of the enzyme was lower than in the acetylation reactions. These results were supported by molecular modelling studies that correctly predicted the maximum stereo selectivity for the cis-isomer of 5-pentyl substituted lactones both in acetylation and in hydrolysis reactions. (C) 2005 Elsevier Ltd. All rights reserved.