| 82190-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• CAS: 82190-19-0
• 化学式: C₆H₇O₃*Na
• 分子量: 150.11
• InChiKey: YVNIKLICDAPIAT-PGMHMLKASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.43
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.36
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  盐酸二甲胺 、 在 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以68%的产率得到(R)-3-Dimethylaminomethyl-5-methyl-dihydro-furan-2-one
  参考文献：
  名称：

  Allergenic .alpha.-methylene-.gamma.-butyrolactones. Stereospecific synthesis of (+)- and (-)-.gamma.-methyl-.alpha.-methylene-.gamma.-butyrolactones. A study of the specificity of (+) and (-) enantiomers in inducing allergic contact dermatitis

  摘要：

  The enantiomers of gamma-methyl-alpha-methylene-gamma-butyrolactone have been prepared stereospecifically from (R)- and (S)-glutamic acid. Three groups of guinea pigs have been sensitized (Feund complete adjuvant technique) to the (+) isomer, the (-) isomer, and the (+/-) mixture. The animals have been tested with each of the enantiomers and with a mixture of the compounds. Only the (-) enantiomer showed some specificity: guinea pigs sensitized to this enantiomer react weakly to the other compound; in turn, animals sensitized to the (+) enantiomer react similarly to both antipodes. Interestingly, reaction to the (+/-) mixture in each group of guinea pigs was the sum of skin responses to the individual enantiomer. These results should be contrasted with sensitization to (+)- and (-)-frullanolides, sesquiterpene lactones for which strong stereospecificity was observed.

  DOI：

  10.1021/jm00350a011
• 作为产物：
  描述：

  (4R)-pentane-1,4-diol 在 Celite 、 sodium hydride 、 silver carbonate 作用下， 以 乙醚 、 乙醇 、 氯仿 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Allergenic .alpha.-methylene-.gamma.-butyrolactones. Stereospecific synthesis of (+)- and (-)-.gamma.-methyl-.alpha.-methylene-.gamma.-butyrolactones. A study of the specificity of (+) and (-) enantiomers in inducing allergic contact dermatitis

  摘要：

  The enantiomers of gamma-methyl-alpha-methylene-gamma-butyrolactone have been prepared stereospecifically from (R)- and (S)-glutamic acid. Three groups of guinea pigs have been sensitized (Feund complete adjuvant technique) to the (+) isomer, the (-) isomer, and the (+/-) mixture. The animals have been tested with each of the enantiomers and with a mixture of the compounds. Only the (-) enantiomer showed some specificity: guinea pigs sensitized to this enantiomer react weakly to the other compound; in turn, animals sensitized to the (+) enantiomer react similarly to both antipodes. Interestingly, reaction to the (+/-) mixture in each group of guinea pigs was the sum of skin responses to the individual enantiomer. These results should be contrasted with sensitization to (+)- and (-)-frullanolides, sesquiterpene lactones for which strong stereospecificity was observed.

  DOI：

  10.1021/jm00350a011