4,4-diethyl-3-hydroxydihydrofuran-2(3H)-one

• 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: 4,4-diethyl-3-hydroxydihydrofuran-2(3H)-one
• 英文别名: (S)-4,4-Diethyl-3-hydroxydihydrofuran-2(3H)-one；(3S)-4,4-diethyl-3-hydroxyoxolan-2-one
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: YSEVXTPQLOXXKJ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-3-Ethyl-2-hydroxy-3-methoxymethyl-pentanoic acid methylamide 在 三溴化硼 、 水 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到4,4-diethyl-3-hydroxydihydrofuran-2(3H)-one
  参考文献：
  名称：

  The synthesis of (S)-(+)-pantolactone and its analogues from an ephedrine-derived morpholinone

  摘要：

  An efficient general route for the enantioselective synthesis of (S)-(+)-pantolactone and its analogues has been developed from an ephedrine-derived chiral morpholin-3-one. Selective dialkylation of an ephedrine-derived chiral template without epimerization is the key step in this synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.022

文献信息

• Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands
  作者：Frederic Bourgeois、Jonathan A. Medlock、Werner Bonrath、Christof Sparr

  DOI：10.1021/acs.orglett.9b04033

  日期：2020.1.3

  A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting

  描述了基于顺序的醛醇加成和转移氢化的催化剂再利用策略，该策略允许获得对映异构体富集的α-羟基-γ-丁内酯。立体选择性的有机催化步骤的组合，然后是有效的催化醛还原，引起随后的内酯​​化，以从容易获得的起始原料中提供对映体富集的丁内酯。通过利用脯氨酸酰胺既充当有机催化剂又充当转移加氢配体的能力，催化剂的再利用允许开发一种操作简单，经济且有效的顺序催化方法。
• A General Method for the Enantioselective Synthesis of Pantolactone Derivatives
  作者：David A. Evans、Jimmy Wu、Craig E. Masse、David W. C. MacMillan

  DOI：10.1021/ol026489d

  日期：2002.10.1

  An efficient enantioselective synthesis of beta,beta-dialkyl-gamma-substituted pantolactones has been achieved utilizing the cationic [Sc((S,S)-R-pybox)](Cl)(2)(+), R = Ph (9), t-Bu (10), complex in a catalyzed aldol reaction as the key step. The pantolactone derivatives are isolated in high enantiomeric excesses. [reaction: see text]

  利用阳离子[Sc（（S，S）-R-pybox）]（Cl）（2）（+），R = Ph（9）实现了β，β-二烷基-γ-取代的泛内酯的有效对映选择性合成），t-Bu（10），在催化的羟醛反应中的配合物是关键步骤。泛内酯衍生物以高对映体过量分离。[反应：看文字]
• Polystyrene-Supported Triphenylsilyl Chloride for the Silylation-Based Kinetic Resolution of Secondary Alcohols
  作者：Ravish K. Akhani、Robert W. Clark、Liang Yuan、Li Wang、Chuanbing Tang、Sheryl L. Wiskur

  DOI：10.1002/cctc.201500173

  日期：2015.5.18

  A silyl chloride derivatized styrene polymer was employed in the silylation‐based kinetic resolution of secondary alcohols for chromatography‐free separation of alcohol enantiomers. Synthetically useful selectivity factors were obtained; furthermore, the polymer was recycled for use in a subsequent kinetic resolution, and it maintained its selectivity and integrity.

  甲硅烷基氯衍生的苯乙烯聚合物用于仲醇的甲硅烷基化动力学拆分中，无需色谱分离即可分离出醇对映体。获得了合成上有用的选择性因子。此外，将聚合物再循环以用于随后的动力学拆分，并且保持其选择性和完整性。
• Kinetic Resolution of Racemic 2-Hydroxy-γ-butyrolactones by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst
  作者：Kenya Nakata、Kouya Gotoh、Keisuke Ono、Kengo Futami、Isamu Shiina

  DOI：10.1021/ol303453j

  日期：2013.3.15

  Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in

  使用新戊酸酐和（R）-苯并四咪唑（（R）-BTM），手性酰基-转移催化剂。重要的是，该新颖方案的底物范围相当广泛（12个例子，s值；最大超过1000）。此外，我们通过理论计算成功地揭示了提供高对映选择性的反应机理，并阐述了2-羟基内酯在C-3位置的取代基效应。
• Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams
  作者：Robert W. Clark、T. Maxwell Deaton、Yan Zhang、Maggie I. Moore、Sheryl L. Wiskur

  DOI：10.1021/ol402982w

  日期：2013.12.20

  A silylation-based kinetic resolution has been developed for alpha-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.