(3S,4R)-4-ethyl-3-hydroxy-4-methyldihydrofuran-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: (3S,4R)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one
• 英文别名: 4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one；(3S,4R)-4-ethyl-3-hydroxy-4-methyloxolan-2-one
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: UDNSVMRLHHBYOK-IYSWYEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (2,1')Z,5S,6R-4,5-dimethyl-2-(1-methylpropylidene)-6-phenylmorpholin-3-one 在 三乙基硅烷 、 硫酸 、 氨 、 水 、 sodium 、 三溴化硼 、 四氯化钛 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 36.09h， 生成 (3S,4R)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective synthesis of pantolactone analogues from an ephedrine-derived morpholine-dione

  摘要：

  An efficient enantioselective synthesis of beta,beta-dialkyl alpha-hydroxy gamma-butyrolactones, analogues of pantolactone, has been developed employing a stereoselective Prins reaction of chiral alkylidene morpholinones, as the key step. Enantioselective synthesis of a naturally occurring pantolactone homologue and a spiro analogue of pantolactone was achieved with this protocol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00408-3

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。
• Synthesis of (±)-pantolactone and (±)-dihydro-4-ethyl-3-hydroxy-4-methyl-2(3<i>H</i>)-furanone
  作者：Takamasa Kinoshita、Madoka Hirano、Hiroyuki Miyake

  DOI：10.1002/jhet.5570280315

  日期：1991.4

  The title compounds were synthesized from 3-furoic acid via the Birch reduction.

  通过Birch还原法由3-糠酸合成标题化合物。
• Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones
  作者：Sunil V Pansare、Annyt Bhattacharyya

  DOI：10.1016/s0040-4039(01)01979-7

  日期：2001.12

  An ephedrine-derived morpholine dione is employed in the synthesis of chiral alkylidene morpholinones that are efficiently converted to beta -substituted alpha-gamma -dihydroxy butyramides, precursors of the corresponding butyrolactones. Enantioselective synthesis of a spiro analog of pantolactone as well as a naturally occurring pantolactone homolog is achieved with this protocol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of pantolactone analogues from an ephedrine-derived morpholine-dione
  作者：Sunil V Pansare、Annyt Bhattacharyya

  DOI：10.1016/s0040-4020(03)00408-3

  日期：2003.4

  An efficient enantioselective synthesis of beta,beta-dialkyl alpha-hydroxy gamma-butyrolactones, analogues of pantolactone, has been developed employing a stereoselective Prins reaction of chiral alkylidene morpholinones, as the key step. Enantioselective synthesis of a naturally occurring pantolactone homologue and a spiro analogue of pantolactone was achieved with this protocol. (C) 2003 Elsevier Science Ltd. All rights reserved.

表征谱图