(S)-5-Butyl-5-methyl-5H-furan-2-one | 137449-38-8

• 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: (S)-5-Butyl-5-methyl-5H-furan-2-one
• 英文别名: (5S)-5-butyl-5-methylfuran-2-one
• CAS: 137449-38-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: RVDMNKURLGETLW-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2S,5S,6R,7S)-5-Butyl-5-methyl-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 以 甲苯 为溶剂， 生成 (S)-5-Butyl-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  Stereoselective construction of quaternary carbon centers. Synthesis of optically active γ,γ-disubstituted γ-butyrolactones.

  摘要：

  An unusually strong solvent effect has been observed on the diastereoselectivity of nucleophilic additions of bromoalkylmagnesium compounds to the lactols 2 and 3, allowing the formation of pure diastereoisomers of 1,4-diols. Homochiral gamma,gamma-disubstituted gamma-butyrolactones could then be obtained after oxidation of these diols followed by a retro Diels-Alder reaction as illustrated by the synthesis of S-(+)-4,5-dimethyl-4-hexanolide.

  DOI：

  10.1016/s0957-4166(00)80463-2

文献信息

• Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers
  作者：Katsufumi Suzuki、Kohei Inomata

  DOI：10.1016/s0040-4039(02)02711-9

  日期：2003.1

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.