4,4-diethyl-4,5-dihydro-3-hydroxy-2(3H)-furanone | 222609-29-2

• 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: 4,4-diethyl-4,5-dihydro-3-hydroxy-2(3H)-furanone
• 英文别名: 3,3-diethyl-2-hydroxy-γ-butyrolactone；4,4-diethyl-3-hydroxydihydrofuran-2(3H)-one；4,4-Diethyl-3-hydroxyoxolan-2-one
• CAS: 222609-29-2
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: YSEVXTPQLOXXKJ-UHFFFAOYSA-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

• 作为反应物：
  描述：

  4,4-diethyl-4,5-dihydro-3-hydroxy-2(3H)-furanone 在 Pt/Al₂O₃ 重铬酸吡啶 、 氢气 、 辛可尼丁 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 10.0~25.0 ℃ 、6.0 MPa 条件下， 反应 28.0h， 生成 (R)-1-cyclohexyl-3-hydroxy-4,4-diethylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Enantioselective hydrogenation of pyrrolidine-2,3,5-triones over the Pt–cinchonidine system

  摘要：

  1- and I-Substituted pyrrolidine-2,3,5-triones 5, 6 and 9 have been synthesized and hydrogenated to 3-hydroxy derivatives 10-12 with 17-91% ee using a 5 wt% Pt/Al2O3 catalyst in the presence of small amounts of cinchonidine. The influence of substituents on the enantioselectivity is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00499-6
• 作为产物：
  描述：

  4,4-二乙基-4,5-二氢呋喃-2,3-二酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以64%的产率得到4,4-diethyl-4,5-dihydro-3-hydroxy-2(3H)-furanone
  参考文献：
  名称：

  Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams

  摘要：

  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.

  DOI：

  10.1021/ol402982w

文献信息

• 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.
• Enantioselective hydrogenation of pyrrolidine-2,3,5-triones over the Pt–cinchonidine system
  作者：A Szabo、N Künzle、T Mallat、A Baiker

  DOI：10.1016/s0957-4166(98)00499-6

  日期：1999.1

  1- and I-Substituted pyrrolidine-2,3,5-triones 5, 6 and 9 have been synthesized and hydrogenated to 3-hydroxy derivatives 10-12 with 17-91% ee using a 5 wt% Pt/Al2O3 catalyst in the presence of small amounts of cinchonidine. The influence of substituents on the enantioselectivity is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.