cis-5-n-Butyl-3-phenyl-4,5-dihydro-2(3H)-furanone

• 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-n-Butyl-3-phenyl-4,5-dihydro-2(3H)-furanone
• 英文别名: 5-butyl-3-phenyltetrahydrofuran-2-one；(3S,5S)-5-butyl-3-phenyloxolan-2-one
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: AWLIUJQQWCNNSY-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  丁基环氧乙烷 、 苯乙酸 在 lithium diethylamide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 cis-5-n-Butyl-3-phenyl-4,5-dihydro-2(3H)-furanone 、 trans-5-n-Butyl-3-phenyl-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  酸烯二醇酯与环氧化物的有效加成

  摘要：

  我们报告了新的条件，以促进将羧酸的二价阴离子添加到环氧化物中，作为使用铝烯醇化物的替代方法。这些条件需要使用亚化学计量 (10%) 量的胺来生成二价阴离子并预先用 LiCl 活化环氧化物。其他路易斯酸已被证明效果较差。产率良好，但仅获得了低的非对映选择性，尽管进行了优化尝试，但仍未得到控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300795

文献信息

• 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.
• Efficient Addition of Acid Enediolates to Epoxides
  作者：Salvador Gil、Mercedes Torres、Natalia Ortúzar、Richard Wincewicz、Margarita Parra

  DOI：10.1002/ejoc.200300795

  日期：2004.5

  We report new conditions to facilitate the addition of dianions of carboxylic acids to epoxides as an alternative method to the use of aluminum enolates. These conditions require the use of a sub-stoichiometric (10%) amount of amine for dianion generation and the previous activation of the epoxide with LiCl. Other Lewis acids have been shown to be less effective. Yields are good but only low diastereoselectivity

  我们报告了新的条件，以促进将羧酸的二价阴离子添加到环氧化物中，作为使用铝烯醇化物的替代方法。这些条件需要使用亚化学计量 (10%) 量的胺来生成二价阴离子并预先用 LiCl 活化环氧化物。其他路易斯酸已被证明效果较差。产率良好，但仅获得了低的非对映选择性，尽管进行了优化尝试，但仍未得到控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)