cis-5-allyl-4,5-dihydro-4-methyl-2(3H)-furanone | 112423-36-6

• 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: cis-5-allyl-4,5-dihydro-4-methyl-2(3H)-furanone
• 英文别名: (4S,5S)-4-methyl-5-prop-2-enyloxolan-2-one
• CAS: 112423-36-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: HLUUBEFBTHTQRB-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  3-formyl-butyric acid methyl ester 、 烯丙基溴化镁 以 乙醚 为溶剂， 反应 2.0h， 生成 trans-4-methyl-5-(2-propenyl)tetrahydro-2-furanone 、 cis-5-allyl-4,5-dihydro-4-methyl-2(3H)-furanone
  参考文献：
  名称：

  Ester groups as effective ligands in chelate-controlled additions of cuprates and Grignard reagents to chiral .beta.-formyl esters to form .gamma.-lactones.

  摘要：

  Addition of cuprates to chiral methyl beta-formyl carboxylates 1a-1d provided gamma-lactones 2-7 in excellent trans-selectivity. The high diastereofacial selectivity was only obtained employing diethyl ether as solvent while tetrahydrofuran gave inferior results. Similar solvent effects were observed in the additions of various Grignard reagents to 1a, which afforded gamma-lactones 2,3,12, and 13 in moderate trans-selectivity. The best solvent for these reactions was dichloromethane. The 1,3-induction of cuprate additions was studied by using aldehydes 8a-8c. The results obtained were interpreted in terms of chelate-controlled additions with formation of seven-membered ring chelates which involve both carbonyl functions of aldehyde 1 or 8. The function of ester groups as effective ligands of lithium or MgX cations may also be of importance for other stereoselective reactions employing organometallic reagents.

  DOI：

  10.1021/jo00075a022

文献信息

• Kunz, Thomas; Janowitz, Agnes; Reissig, Hans-Ulrich, Chemische Berichte, 1989, vol. 122, p. 2165 - 2176
  作者：Kunz, Thomas、Janowitz, Agnes、Reissig, Hans-Ulrich

  DOI：——

  日期：——
• Kunz, Thomas; Reissig, Hans-Ulrich, Angewandte Chemie, 1988, vol. 100, # 2, p. 297 - 298
  作者：Kunz, Thomas、Reissig, Hans-Ulrich

  DOI：——

  日期：——
• Kunz, Thomas; Reissig, Hans-Ulrich, Liebigs Annalen der Chemie, 1989, p. 891 - 894
  作者：Kunz, Thomas、Reissig, Hans-Ulrich

  DOI：——

  日期：——
• Ester groups as effective ligands in chelate-controlled additions of cuprates and Grignard reagents to chiral .beta.-formyl esters to form .gamma.-lactones.
  作者：Hans Ulrich Reissig、Hubert Angert、Thomas Kunz、Agnes Janowitz、Gabriele Handke、Emanuel Bruce-Adjei

  DOI：10.1021/jo00075a022

  日期：1993.11

  Addition of cuprates to chiral methyl beta-formyl carboxylates 1a-1d provided gamma-lactones 2-7 in excellent trans-selectivity. The high diastereofacial selectivity was only obtained employing diethyl ether as solvent while tetrahydrofuran gave inferior results. Similar solvent effects were observed in the additions of various Grignard reagents to 1a, which afforded gamma-lactones 2,3,12, and 13 in moderate trans-selectivity. The best solvent for these reactions was dichloromethane. The 1,3-induction of cuprate additions was studied by using aldehydes 8a-8c. The results obtained were interpreted in terms of chelate-controlled additions with formation of seven-membered ring chelates which involve both carbonyl functions of aldehyde 1 or 8. The function of ester groups as effective ligands of lithium or MgX cations may also be of importance for other stereoselective reactions employing organometallic reagents.