(2R,4S)-(-)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid | 284494-68-4

• 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: (2R,4S)-(-)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid
• 英文别名: (2R,4S)-4-methyl-5-oxooxolane-2-carboxylic acid
• CAS: 284494-68-4
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: VVRZSEJAVZUPSO-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2R,4S)-(-)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid 生成 methyl (2R,4S)-(-)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylate
  参考文献：
  名称：

  Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters

  摘要：

  Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned gamma-lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00057-4
• 作为产物：
  描述：

  diethyl 2-hydroxy-4-methylpentanedioate 在 sodium hydroxide 、 phosphate buffer 、 对甲苯磺酸 、 α-chymotrypsin 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (2R,4S)-(-)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters

  摘要：

  Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned gamma-lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00057-4

文献信息

• Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters
  作者：Sara Drioli、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(00)00057-4

  日期：2000.4

  Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned gamma-lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd. All rights reserved.