cis-(RS,SR)-γ-hydroxy-β-methyl-γ-<2-(methylthio)phenyl>butanoic acid lactone | 133101-61-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: cis-(RS,SR)-γ-hydroxy-β-methyl-γ-<2-(methylthio)phenyl>butanoic acid lactone
• 英文别名: (4S,5R)-4-methyl-5-(2-methylsulfanylphenyl)oxolan-2-one
• CAS: 133101-61-8；133127-84-1
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: VHBSMKBURMJAGF-QPUJVOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲硫基苯甲醛 在 4-二甲氨基吡啶 、 sodium hydroxide 、 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide methyl toluene-p-sulphonate 、 Celite 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 pyridinium chlorochromate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 cis-(RS,SR)-γ-hydroxy-β-methyl-γ-<2-(methylthio)phenyl>butanoic acid lactone
  参考文献：
  名称：

  Stereoselective reduction of .gamma.-oxobutanoic acids using DIBAL-H and zinc chloride

  摘要：

  A variety of gamma-aromatic gamma-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-gamma-aryl-gamma-hydroxy-beta-methylbutanoic acids. Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity. Also we have shown that some gamma-aryl-gamma-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.

  DOI：

  10.1021/jo00009a030

文献信息

• Stereoselective reduction of .gamma.-oxobutanoic acids using DIBAL-H and zinc chloride
  作者：R. Frenette、M. Monette、M. A. Bernstein、R. N. Young、T. R. Verhoeven

  DOI：10.1021/jo00009a030

  日期：1991.4

  A variety of gamma-aromatic gamma-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-gamma-aryl-gamma-hydroxy-beta-methylbutanoic acids. Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity. Also we have shown that some gamma-aryl-gamma-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.