(S)-4-hydroxy-2-oxa-spiro[4.4]nonan-3-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: (S)-4-hydroxy-2-oxa-spiro[4.4]nonan-3-one
• 英文别名: 4-hydroxy-2-oxaspiro[4.4]nonan-3-one；(S)-4-Hydroxy-2-oxaspiro[4.4]nonan-3-one；(4S)-4-hydroxy-2-oxaspiro[4.4]nonan-3-one
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: WKCZDDXNJWASQB-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  2-Allyl-2-((2S,5S,6R)-4,5-dimethyl-3-oxo-6-phenyl-morpholin-2-yl)-pent-4-enoic acid ethyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 氨 、 氢气 、 sodium 、 三溴化硼 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.05h， 生成 (S)-4-hydroxy-2-oxa-spiro[4.4]nonan-3-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]
• 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.
• The synthesis of (S)-(+)-pantolactone and its analogues from an ephedrine-derived morpholinone
  作者：Bidhan A. Shinkre、Abdul Rakeeb A.S. Deshmukh

  DOI：10.1016/j.tetasy.2004.02.022

  日期：2004.4

  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.