(4R,5S)-4,5-dihydro-5-(hydroxymethyl)-4-vinyl-2(3H)furanon | 66601-85-2

• 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,5S)-4,5-dihydro-5-(hydroxymethyl)-4-vinyl-2(3H)furanon
• 英文别名: (2S,3R)-2-hydroxymethyl-3-vinyl-γ-butyrolactone；(4R,5S)-4-ethenyl-5-(hydroxymethyl)oxolan-2-one
• CAS: 66601-85-2
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: MIINWKKZEJVIBD-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (4R,5S)-4,5-dihydro-5-(hydroxymethyl)-4-vinyl-2(3H)furanon 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4R,5S)-5-<<(tert-Butyldimethylsilyl)oxy>methyl>-4-ethenyl-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
• 作为产物：
  描述：

  (S)-(+)-3-(2,2-二甲基-1,3-二噁戊环-4-基)-反-2-丙烯酸甲酯 在 diisobutylaluminum hydride 、 硫酸 、 丙酸 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (4R,5S)-4,5-dihydro-5-(hydroxymethyl)-4-vinyl-2(3H)furanon
  参考文献：
  名称：

  Suzuki, Toshio; Sato, Etsuko; Kamada, Shinko, Journal of the Chemical Society. Perkin transactions I, 1986, p. 387 - 392

  摘要：

  DOI：

文献信息

• Brueckner, Reinhard, Chemische Berichte, 1989, vol. 122, p. 703 - 710
  作者：Brueckner, Reinhard

  DOI：——

  日期：——
• Kametani, Tetsuji; Suzuki, Toshio; Nishimura, Masahiro, Heterocycles, 1982, vol. 19, # 2, p. 205 - 208
  作者：Kametani, Tetsuji、Suzuki, Toshio、Nishimura, Masahiro、Sato, Etsuko、Unno, Katsuo

  DOI：——

  日期：——
• BRUCKNER, REINHARD, CHEM. BER., 122,(1989) N, C. 713-710
  作者：BRUCKNER, REINHARD

  DOI：——

  日期：——
• 1,2-Asymmetric Induction in the Zwitterionic Claisen Rearrangement of Allylamines
  作者：Udo Nubbemeyer

  DOI：10.1021/jo00117a032

  日期：1995.6

  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.
• Suzuki, Toshio; Sato, Etsuko; Kamada, Shinko, Journal of the Chemical Society. Perkin transactions I, 1986, p. 387 - 392
  作者：Suzuki, Toshio、Sato, Etsuko、Kamada, Shinko、Tada, Hitoshi、Unno, Katsuo、Kametani, Tetsuii

  DOI：——

  日期：——