5-hydroxy-5-methyl-3-(2-phenylethyl)-2(5H)-furanone | 186449-48-9

• 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: 5-hydroxy-5-methyl-3-(2-phenylethyl)-2(5H)-furanone
• 英文别名: 5-Hydroxy-5-methyl-3-(2-phenylethyl)furan-2-one
• CAS: 186449-48-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: IZUBNAQBZCEQDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  5-hydroxy-5-methyl-3-(2-phenylethyl)-2(5H)-furanone 在 盐酸 作用下， 反应 3.0h， 以52%的产率得到(+/-)-4-benzyl-3-hydroxy-5-(2-phenylethyl)-2(5H)-furanone
  参考文献：
  名称：

  Dehydration of 2-(2-Arylethyl)-2-hydroxy-4-oxopentanoic Acids and their hydrazones to form heterocycles

  摘要：

  Dehydration of 2-(2-arylethyl)-2-hydroxy-4-oxopentanoic acids 1 with hydrochloric acid/acetic acid, affords 3-(2-arylethyl)-5-hydroxy-5-methyl-2(5H)-furanones 4. Compounds of type 1 and 4 represent suitable precursors for the formation of pyridazin-3-ones 7 as they smoothly react with hydrazine. A new series of s-triazolo[4,3-b]pyridazin-3-ones 12 and tetrazolo[1,5-b]pyridazines 15 are obtained from the 3-chloropyridazines 11 upon treatment with semicarbazide and sodium azide, respectively. Reaction of 11 with phenyl- acetyl-hydrazine provides 3-benzyl-6-phenyl-8-(2-phenyl-ethyl)-s-triazolo [4,3-b]pyridazine 13 via dehydrative cyclization of the intermediate 14 which was clarified to exhibit tautomeric equilibria between enol-hydrazine form A and keto-hydrazine form B by means of H-1 and C-13 NMR spectroscopy. Attempts to synthesize 3-alloxy-pyridazines 18 by reacting 11 with sodium alloxide afford N-allyl compounds 17.

  DOI：

  10.1002/prac.19973390104
• 作为产物：
  描述：

  2-Hydroxy-2-phenethyl-4-oxo-pentansaeure 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以39.4%的产率得到5-hydroxy-5-methyl-3-(2-phenylethyl)-2(5H)-furanone
  参考文献：
  名称：

  Dehydration of 2-(2-Arylethyl)-2-hydroxy-4-oxopentanoic Acids and their hydrazones to form heterocycles

  摘要：

  Dehydration of 2-(2-arylethyl)-2-hydroxy-4-oxopentanoic acids 1 with hydrochloric acid/acetic acid, affords 3-(2-arylethyl)-5-hydroxy-5-methyl-2(5H)-furanones 4. Compounds of type 1 and 4 represent suitable precursors for the formation of pyridazin-3-ones 7 as they smoothly react with hydrazine. A new series of s-triazolo[4,3-b]pyridazin-3-ones 12 and tetrazolo[1,5-b]pyridazines 15 are obtained from the 3-chloropyridazines 11 upon treatment with semicarbazide and sodium azide, respectively. Reaction of 11 with phenyl- acetyl-hydrazine provides 3-benzyl-6-phenyl-8-(2-phenyl-ethyl)-s-triazolo [4,3-b]pyridazine 13 via dehydrative cyclization of the intermediate 14 which was clarified to exhibit tautomeric equilibria between enol-hydrazine form A and keto-hydrazine form B by means of H-1 and C-13 NMR spectroscopy. Attempts to synthesize 3-alloxy-pyridazines 18 by reacting 11 with sodium alloxide afford N-allyl compounds 17.

  DOI：

  10.1002/prac.19973390104