(S)-4-hydroxy-2-oxa-spiro[4.5]decan-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[4.5]decan-3-one
• 英文别名: 4S-4-hydroxy-2-oxa-spiro[4,5]decan-3-one；4-hydroxy-2-oxaspiro[4.5]decan-3-one；(4S)-4-hydroxy-2-oxaspiro[4.5]decan-3-one
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: OOGYDVXOZPLMGG-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  苯甲酰氯 、 (S)-4-hydroxy-2-oxa-spiro[4.5]decan-3-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  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
• 作为产物：
  描述：

  2R,3S,6R-3,4-dimethyl-2-phenyl-1,14,16-trioxa-4-aza-dispiro[5.0.5.4]hexadecane-5-one 在 三乙基硅烷 、 氨 、 sodium 、 三溴化硼 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S)-4-hydroxy-2-oxa-spiro[4.5]decan-3-one
  参考文献：
  名称：

  Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)01979-7

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]
• 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.
• 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 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.