(5R)-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one | 1193320-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5R)-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one
• 英文别名: (2R)-2-(3-methylbut-2-enyl)-3-pyrrolidin-1-yl-2H-furan-5-one
• CAS: 1193320-08-9
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: YAUFEWHNFYSFLK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one 在 氨 、 lithium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (5R)-5-(3-methylbut-2-enyl)-2,5-dihydrofuran-2-ol
  参考文献：
  名称：

  Asymmetric [2,3]-Wittig rearrangement of the dienolates of chiral secondary alcohol-substituted β-pyrrolidinyl-γ-allyloxyl-α,β-unsaturated esters: total synthesis of (+)-eldanolide

  摘要：

  The asymmetric [2,3]-Wittig rearrangement of the dienolates of various chiral beta-pyrrolidinyl-gamma-allyloxyl-alpha,beta-unsaturated esters was investigated using different chiral secondary alcohol Substitutions. When (1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2,2,1]heptane-1-carboxylic acid diisopropylamide was used as chiral auxiliary, it provided the best enantioselectivity in the rearrangement. When various gamma-allyloxy substitutions underwent temperature and additive studies, 1,1-dimethylpropenoxy substitution was found to give the best enantioselectivity. The methodology was applied to the total synthesis of eldanolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.028
• 作为产物：
  描述：

  4-(1,1-dimethyl-allyloxy)-3-pyrrolidin-1-ylbut-2-enoic acid (1R,2S)-1-diisopropylcarbamoyl-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 lithium bromide 、 lithium diisopropyl amide 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到(5R)-(3-methyl-but-2-enyl)-4-pyrrolidin-1-yl-5H-furan-2-one
  参考文献：
  名称：

  Asymmetric [2,3]-Wittig rearrangement of the dienolates of chiral secondary alcohol-substituted β-pyrrolidinyl-γ-allyloxyl-α,β-unsaturated esters: total synthesis of (+)-eldanolide

  摘要：

  The asymmetric [2,3]-Wittig rearrangement of the dienolates of various chiral beta-pyrrolidinyl-gamma-allyloxyl-alpha,beta-unsaturated esters was investigated using different chiral secondary alcohol Substitutions. When (1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2,2,1]heptane-1-carboxylic acid diisopropylamide was used as chiral auxiliary, it provided the best enantioselectivity in the rearrangement. When various gamma-allyloxy substitutions underwent temperature and additive studies, 1,1-dimethylpropenoxy substitution was found to give the best enantioselectivity. The methodology was applied to the total synthesis of eldanolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.028