(4S,5S)-4-Ethenyl-5-methyl-2(3H)-furanone | 97387-89-8

• 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: (4S,5S)-4-Ethenyl-5-methyl-2(3H)-furanone
• CAS: 97387-89-8
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: YFRZAYUAZJHSGE-NTSWFWBYSA-N

物化性质

• 沸点：
  213.5±29.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 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：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-<(3S,4S)-3-Ethenyl-4-<(tert-butyldimethylsilyl)oxy>pentanoyl>pyrrolidine 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以91.6%的产率得到(4S,5S)-4-Ethenyl-5-methyl-2(3H)-furanone
  参考文献：
  名称：

  1,2-Asymmetric Induction in the Zwitterionic Claisen Rearrangement of Allylamines

  摘要：

  A zwitterionic Claisen rearrangement has been developed for optically active N-allylpyrrolidines using a two-phase system. The inherent-1,2 asymmetric induction was investigated for the generation of a new C-C bond adjacent to a chiral C-O function. The reaction with acetyl chloride led to a small diastereomeric excess, whereas the rearrangement with propionyl chloride proceeded with a high simple and a high induced diastereoselection. The resulting gamma,delta-unsaturated amides were cyclized to the corresponding optically active gamma-butyrolactones, which are useful intermediates in natural product synthesis.

  DOI：

  10.1021/jo00117a032

文献信息

• Enantioselective synthesis of (−)-elenolic acid and (−)-ajmalicine
  作者：Susumi Hatakeyama、Keiichi Saijo、Seiichi Takano

  DOI：10.1016/s0040-4039(00)61950-0

  日期：1985.1

  A secoiridoid monoterpene (−)-elenolic acid and a representative heteroyohimbine alkaloid (−)-ajmalicine have been synthesized enantio- and stereoselectively using L-ethyl lactate as a chiral starting material.

  使用乳酸L-乙酯作为手性原料，对映体和立体选择性地合成了类二十碳四烯单萜（-）-烯丙酸和代表性的异育亨宾生物碱（-）-ajmalicine。