3-methylene-4(R),5(S)-dimethyldihydro-2-furanone | 110171-21-6

• 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: 3-methylene-4(R),5(S)-dimethyldihydro-2-furanone
• 英文别名: (4R,5S)-4,5-dimethyl-3-methylideneoxolan-2-one
• CAS: 110171-21-6
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: GWSGIIGWNQXFIJ-XINAWCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 碘甲烷 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 3-methylene-4(R),5(S)-dimethyldihydro-2-furanone
  参考文献：
  名称：

  Stereospecificity in allergic contact dermatitis to simple substituted methylene lactones derivatives

  摘要：

  The enantiomers of beta,gamma-dimethyl- and beta-methyl-alpha-methylene-gamma-butyrolactones have been synthesized stereospecifically from glutamic acid and beta-hydroxy isobutyric acid, respectively. Guinea pigs have been sensitized (Freund complete adjuvant technique) and tested to them. Both enantiomers of beta-methyl lactone as well as (+)-beta,gamma-dimethyl lactone induced enantiospecific allergic contact dermatitis (ACD); in turn, (-)-beta,gamma-dimethyl lactone showed no specificity. An interpretation is proposed.

  DOI：

  10.1021/jm00394a003

文献信息

• MATTES, HENRI;HAMADA, KAORU;BENEZRA, CLAUDE, J. MED. CHEM., 30,(1987) N 11, 1948-1951
  作者：MATTES, HENRI、HAMADA, KAORU、BENEZRA, CLAUDE

  DOI：——

  日期：——
• Stereospecificity in allergic contact dermatitis to simple substituted methylene lactones derivatives
  作者：Henri Mattes、Kaoru Hamada、Claude Benezra

  DOI：10.1021/jm00394a003

  日期：1987.11

  The enantiomers of beta,gamma-dimethyl- and beta-methyl-alpha-methylene-gamma-butyrolactones have been synthesized stereospecifically from glutamic acid and beta-hydroxy isobutyric acid, respectively. Guinea pigs have been sensitized (Freund complete adjuvant technique) and tested to them. Both enantiomers of beta-methyl lactone as well as (+)-beta,gamma-dimethyl lactone induced enantiospecific allergic contact dermatitis (ACD); in turn, (-)-beta,gamma-dimethyl lactone showed no specificity. An interpretation is proposed.