(5S)-5-[(4-methoxyphenyl)methyl]oxolan-2-one | 1227746-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5S)-5-[(4-methoxyphenyl)methyl]oxolan-2-one
• CAS: 1227746-64-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: RSMLDVUFWAZZMF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-ethyl 4-hydroxy-5-(4-methoxyphenyl)pentanoate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (5S)-5-[(4-methoxyphenyl)methyl]oxolan-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of syn/anti-1,3-Amino Alcohols via Proline-Catalyzed Sequential α-Aminoxylation/α-Amination and Horner−Wadsworth−Emmons Olefination of Aldehydes

  摘要：

  A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential alpha-aminoxylation/alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5-phenylpentan-2-ol, is also accomplished.

  DOI：

  10.1021/ol100856u

文献信息

• Repurposing Visible‐Light‐Excited Ene‐Reductases for Diastereo‐ and Enantioselective Lactones Synthesis
  作者：Jinhai Yu、Qiaoyu Zhang、Beibei Zhao、Tianhang Wang、Yu Zheng、Binju Wang、Yan Zhang、Xiaoqiang Huang

  DOI：10.1002/anie.202402673

  日期：2024.7

  A dual bio-/photocatalytic system has been developed for achieving previously elusive diastereo- and enantioselective radical lactonizations. By integrating directed evolution and photoinduced single-electron oxidation, we repurposed engineered ene-reductases to steer non-natural radical C−O formations giving a diverse array of enantioenhanced 5- and 6-membered lactones with vicinal stereocenters,

  已经开发出双重生物/光催化系统，用于实现以前难以实现的非对映选择性和对映选择性自由基内酯化。通过整合定向进化和光诱导单电子氧化，我们重新利用了工程烯还原酶来引导非天然自由基C−O形成，从而提供了多种具有邻位立构中心的对映增强型5元和6元内酯，其中部分带有季铵基团立体中心。