(4R,5R)-5-Bromomethyl-4-methyl-dihydro-furan-2-one | 84911-46-6

• 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: (4R,5R)-5-Bromomethyl-4-methyl-dihydro-furan-2-one
• 英文别名: (4R,5R)-5-(bromomethyl)-4-methyloxolan-2-one
• CAS: 84911-46-6
• 化学式: C₆H₉BrO₂
• 分子量: 193.04
• InChiKey: YREXBMZUQTXMQU-UHNVWZDZSA-N

物化性质

• 沸点：
  289.6±13.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-Bromomethyl-4-methyl-dihydro-furan-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成
  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
• 作为产物：
  描述：

  (2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one 在 copper(l) iodide 、 四溴化碳 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.17h， 生成 (4R,5R)-5-Bromomethyl-4-methyl-dihydro-furan-2-one
  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

• Study on the Bromolactonisation of Alkenoic Acids with (Diacetoxyiodo)Benzene
  作者：Yan He、Zhenping Yang、Jie Yan

  DOI：10.3184/030823410x12682297999384

  日期：2010.3

  A study on the bromolactonisation of alkenoic acids is reported. When various pent-4-enoic acids reacted with (diacetoxyiodo)benzene (DIB) and lithium bromide in CH3OH at room temperature, most of the five-membered bromolactones were obtained in good to excellent yields in short times. Some had two diastereoisomers. When but-3-enoic acid and trans-hex-3-enoic acid were treated under the same conditions

  报道了关于烯酸的溴内酯化的研究。当各种戊 4-烯酸与（二乙酰氧基碘）苯 (DIB) 和溴化锂在 CH3OH 中在室温下反应时，大多数五元溴内酯在短时间内以良好到极好的收率获得。有些具有两种非对映异构体。当丁-3-烯酸和反式-己-3-烯酸在相同条件下处理时，后处理后仅发现不饱和内酯。然而，当 6-5-烯酸处于相同条件时，目标六元溴内酯未能成功分离。