(S)-6-(1R,2R)-2-((hydroxymethyl)cyclopropyl)tetrahydropyran-2-one | 1035930-91-6

• 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)-6-(1R,2R)-2-((hydroxymethyl)cyclopropyl)tetrahydropyran-2-one
• CAS: 1035930-91-6
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: VONPPLFSOLDSCE-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-6-(1R,2R)-2-((hydroxymethyl)cyclopropyl)tetrahydropyran-2-one 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以76%的产率得到2-(tetrahydro-6-oxo-2H-pyran-2-yl)-<1α,2β(S)>-cyclopropanecarboxaldehyde
  参考文献：
  名称：

  Enantioselective Total Synthesis of Eicosanoid and Its Congener, Using Organocatalytic Cyclopropanation, and Catalytic Asymmetric Transfer Hydrogenation Reactions as Key Steps

  摘要：

  An enantioselective unified strategy for the syntheses of the oxylipin class of natural products was accomplished. Our strategy relies on three catalytic steps: (a) organocatalytic cyclopropanation, (b) the catalytic asymmetric transfer hydrogenation (CATHy) reaction, and (c) the Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo800631z
• 作为产物：
  描述：

  (S)-6-((1R,2R)-2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)tetrahydropyran-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以70%的产率得到(S)-6-(1R,2R)-2-((hydroxymethyl)cyclopropyl)tetrahydropyran-2-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of Eicosanoid and Its Congener, Using Organocatalytic Cyclopropanation, and Catalytic Asymmetric Transfer Hydrogenation Reactions as Key Steps

  摘要：

  An enantioselective unified strategy for the syntheses of the oxylipin class of natural products was accomplished. Our strategy relies on three catalytic steps: (a) organocatalytic cyclopropanation, (b) the catalytic asymmetric transfer hydrogenation (CATHy) reaction, and (c) the Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo800631z