3,6-dihexyl-4-hydroxy-2H-pyran-2-one | 233255-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3,6-dihexyl-4-hydroxy-2H-pyran-2-one
• 英文别名: 3,6-Dihexyl-4-hydroxypyran-2-one
• CAS: 233255-60-2
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: ZXPFDGSMLJREOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  3,6-dihexyl-4-hydroxy-2H-pyran-2-one 在 ruthenium catalyst with atropoisomeric (S)-ligand tetrafluoroboric acid 、 氢气 作用下， 以 水 、 异丙醇 为溶剂， 60.0 ℃ 、6.0 MPa 条件下， 反应 20.0h， 以96%的产率得到(-)-3,6-dihexyl-5,6-dihydro-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Asymmetric Hydrogenation of Substituted 2-Pyrones

  摘要：

  Various substituted 2-pyrones have been hydrogenated with high enantioselectivity (up to 97% ee) to the corresponding 5,6-dihydropyrones using cationic ruthenium catalysts containing the (6,6'-dimethoxybiphenyl-2,2'diyl)bis[3,5-di(tert-butyl)phenylphosphine] ligand. When substituents at position 3 are absent, 5,6-dihydropyrones are further hydrogenated to the fully saturated delta-lactones. In the case of 4,6-dimethyl-2H-pyran-2-one, the diastereoselectivity of the second hydrogenation step was determined by the chirality of the applied catalyst, while for the 4,5,6-trimethyl-2H-pyran-2-one a double asymmetric induction effect was observed. Other cyclic substrates with endo- or exocyclic double bonds were hydrogenated, although with substantially lower enantioselectivity with respect to the 2-pyrones.

  DOI：

  10.1021/jo982215l
• 作为产物：
  描述：

  庚酸甲酯 在 正丁基锂 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 3,6-dihexyl-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Asymmetric Hydrogenation of Substituted 2-Pyrones

  摘要：

  Various substituted 2-pyrones have been hydrogenated with high enantioselectivity (up to 97% ee) to the corresponding 5,6-dihydropyrones using cationic ruthenium catalysts containing the (6,6'-dimethoxybiphenyl-2,2'diyl)bis[3,5-di(tert-butyl)phenylphosphine] ligand. When substituents at position 3 are absent, 5,6-dihydropyrones are further hydrogenated to the fully saturated delta-lactones. In the case of 4,6-dimethyl-2H-pyran-2-one, the diastereoselectivity of the second hydrogenation step was determined by the chirality of the applied catalyst, while for the 4,5,6-trimethyl-2H-pyran-2-one a double asymmetric induction effect was observed. Other cyclic substrates with endo- or exocyclic double bonds were hydrogenated, although with substantially lower enantioselectivity with respect to the 2-pyrones.

  DOI：

  10.1021/jo982215l

文献信息

• Asymmetric Hydrogenation of Substituted 2-Pyrones
  作者：Matthias J. Fehr、Giambattista Consiglio、Michelangelo Scalone、Rudolf Schmid

  DOI：10.1021/jo982215l

  日期：1999.8.1

  Various substituted 2-pyrones have been hydrogenated with high enantioselectivity (up to 97% ee) to the corresponding 5,6-dihydropyrones using cationic ruthenium catalysts containing the (6,6'-dimethoxybiphenyl-2,2'diyl)bis[3,5-di(tert-butyl)phenylphosphine] ligand. When substituents at position 3 are absent, 5,6-dihydropyrones are further hydrogenated to the fully saturated delta-lactones. In the case of 4,6-dimethyl-2H-pyran-2-one, the diastereoselectivity of the second hydrogenation step was determined by the chirality of the applied catalyst, while for the 4,5,6-trimethyl-2H-pyran-2-one a double asymmetric induction effect was observed. Other cyclic substrates with endo- or exocyclic double bonds were hydrogenated, although with substantially lower enantioselectivity with respect to the 2-pyrones.