(2S,4S)-(-)-cis-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid | 88218-42-2

• 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: (2S,4S)-(-)-cis-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid
• 英文别名: (2S,4S)-4-Carboxy-2-methylbutan-4-olide；(2S,4S)-4-methyl-5-oxooxolane-2-carboxylic acid
• CAS: 88218-42-2
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: VVRZSEJAVZUPSO-IMJSIDKUSA-N

物化性质

• 沸点：
  372.7±35.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

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：

  (2S,4S)-(-)-cis-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid 在 Pd-BaSO₄ 氯化亚砜 、 四甲基硫脲 、 氢气 作用下， 以 甲苯 为溶剂， 生成 (2S,4S)-4-Methyl-5-oxo-tetrahydro-furan-2-carbaldehyde
  参考文献：
  名称：

  Nishida, Yoshihiro; Ohrui, Hiroshi; Meguro, Hiroshi, Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2123 - 2126

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl 2-hydroxy-4-methylpentanedioate 在 sodium hydroxide 、 phosphate buffer 、 Porcine pancreatic lipase type II 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (2S,4S)-(-)-cis-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

• Nishida, Yoshihiro; Ohrui, Hiroshi; Meguro, Hiroshi, Agricultural and Biological Chemistry, 1984, vol. 48, # 5, p. 1211 - 1216
  作者：Nishida, Yoshihiro、Ohrui, Hiroshi、Meguro, Hiroshi

  DOI：——

  日期：——
• 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.
• Nishida, Yoshihiro; Ohrui, Hiroshi; Meguro, Hiroshi, Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2123 - 2126
  作者：Nishida, Yoshihiro、Ohrui, Hiroshi、Meguro, Hiroshi

  DOI：——

  日期：——

表征谱图