(S)-5-propyl-5-phenyl-dihydrofuran-2-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)-5-propyl-5-phenyl-dihydrofuran-2-one
• 英文别名: (5S)-5-phenyl-5-propyloxolan-2-one
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: LPLMJUDRRZXURD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丁酮 、 丙烯酰氯 在 Wang-resin supported (1R,2S)-ephedrine 、 三乙胺 、 samarium diiodide 作用下， 以 乙醚 、 四氢呋喃 、 叔丁醇 为溶剂， 生成 (S)-5-propyl-5-phenyl-dihydrofuran-2-one 、 (R)-5-propyl-5-phenyl-dihydrofuran-2-one
  参考文献：
  名称：

  Application of an ephedrine chiral linker in a solid-phase, ‘asymmetric catch-release’ approach to γ-butyrolactones

  摘要：

  一种以Sm(II)为媒介的非对称分子间酮基-烯烃加成反应，采用通过“麻黄碱手性连接”与树脂相连的α,β-不饱和酯，已被应用于直接的“非对称捕获-释放”方法，以合成γ-丁内酯。

  DOI：

  10.1039/b302471g

文献信息

• SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES
  申请人：Kansas State University Research Foundation

  公开号：US20200306737A1

  公开（公告）日：2020-10-01

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

  手性聚乙烯吡咯烷酮（CSPVP），CSPVP与金属纳米团簇催化剂等核心物种形成的络合物，以及利用这种络合物进行对映选择氧化反应的方法被揭示。CSPVP络合物可用于不对称二醇氧化、烯烃对映选择氧化以及碳-碳键形成反应等。CSPVP还可以与蛋白质、DNA和RNA等生物分子形成络合物，并用作siRNA或dsRNA传递的纳米载体。
• CHIRAL-SUBSTITUTED POLY-N-VINYLPYRROLIDINONES AND COMPLEXES WITH BIMETALLIC NANOCLUSTERS AND USES THEREOF IN ASYMMETRIC OXIDATION REACTIONS
  申请人：Kansas State University Research Foundation

  公开号：US20220204447A1

  公开（公告）日：2022-06-30

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a bimetallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The catalytic complexes have exhibited the ability to achieve reaction products have a very high degree of optical purifies. These reaction products can be used as reagents in the synthesis of complex organic molecules, such as bioactive products, and C—H bond oxidation of complex molecules including various drugs and natural products.

  本发明公开了手性聚乙烯吡咯烷酮（CSPVP）及其与核心物种（例如双金属纳米簇催化剂）的配合物，以及利用这些配合物进行对映选择性氧化反应。这些催化配合物已经表现出实现反应产物具有非常高的光学纯度的能力。这些反应产物可用作复杂有机分子（如生物活性产物）的合成试剂，并用于包括各种药物和天然产物在内的复杂分子的C-H键氧化。
• Synthesis and application of chiral substituted polyvinylpyrrolidinones
  申请人：Kansas State University Research Foundation

  公开号：US10906033B2

  公开（公告）日：2021-02-02

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

  本发明公开了手性聚乙烯基吡咯烷酮（CSPVP）、CSPVP 与核心物质（如金属纳米簇催化剂）的络合物以及利用此类络合物进行的对映选择性氧化反应。例如，CSPVP 复合物可用于二元醇的不对称氧化、烯烃的对映选择性氧化和碳-碳键形成反应。CSPVP 还可与蛋白质、DNA 和 RNA 等生物大分子络合，用作 siRNA 或 dsRNA 输送的纳米载体。
• [EN] CHIRAL-SUBSTITUTED POLY-N-VINYLPYRROLIDINONES AND COMPLEXES WITH BIMETALLIC NANOCLUSTERS AND USES THEREOF IN ASYMMETRIC OXIDATION REACTIONS<br/>[FR] POLY-N-VINYLEPYRROLIDINONES SUBSTITUÉES CHIRALES ET COMPLEXES COMPORTANT DES NANOAGRÉGATS BIMÉTALLIQUES ET LEURS UTILISATIONS DANS DES RÉACTIONS D'OXYDATION ASYMÉTRIQUES
  申请人：UNIV KANSAS STATE

  公开号：WO2020163295A1

  公开（公告）日：2020-08-13

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a bimetallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The catalytic complexes have exhibited the ability to achieve reaction products have a very high degree of optical purities. These reaction products can be used as reagents in the synthesis of complex organic molecules, such as bioactive products, and C-H bond oxidation of complex molecules including various drugs and natural products.
• Application of an ephedrine chiral linker in a solid-phase, ‘asymmetric catch-release’ approach to γ-butyrolactones
  作者：Nessan J. Kerrigan、Panee C. Hutchison、Tom D. Heightman、David J. Procter

  DOI：10.1039/b302471g

  日期：——

  A Sm(II)-mediated, asymmetric, intermolecular ketyl-olefin addition employing α,β-unsaturated esters linked to resin through an ephedrine ‘chiral link’ has been applied in a direct ‘asymmetric catch-release’ approach to γ-butyrolactones.

  一种以Sm(II)为媒介的非对称分子间酮基-烯烃加成反应，采用通过“麻黄碱手性连接”与树脂相连的α,β-不饱和酯，已被应用于直接的“非对称捕获-释放”方法，以合成γ-丁内酯。