5-benzyloxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran-2-one | 863910-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-benzyloxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran-2-one
• 英文别名: Methyl 2-(3-methyl-2-oxo-5-phenylmethoxy-1-benzofuran-3-yl)acetate
• CAS: 863910-99-0
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: TXGSVVMOCFMNSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以65%的产率得到2-(5'-benzyloxyphenyl-2'-hydroxy)-2-methyl-1,4-butanediol
  参考文献：
  名称：

  Syntheses of Tetrahydrofurobenzofurans and Dihydromethanobenzodioxepines from 5-Hydroxy-3-methyl-3H-benzofuran-2-one. Rearrangement and Ring Expansion under Reductive Conditions on Treatment with Hydrides

  摘要：

  5-Hydroxy-3-methyl-3H-benzofuran-2-one, 5, easily obtained from pyruvic acid and 1,4-cyclohexanedione, was used as a starting material to prepare ()-5-hydroxy-3a-methyl-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran, 10, and ()-7-hydroxy-5-methyl-4,5-dihydro-2,5-methano-1,3-benzodioxepine, 14. Reduced reactivity relative to 5-hydroxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran2-one, 6, was preliminarily studied. Meanwhile, a plausible mechanism with regard to the formation of 10 and 14, which included cyclization, rearrangement, and ring expansion of hemiacetal, 15, is proposed. Specific carbamates of phenols, 10 and 14, have shown impressive inhibitory activities against human acetyleholinesterase (AChE) and butyrylcholinesterase (BChE) ex vivo.

  DOI：

  10.1021/jo0503052
• 作为产物：
  描述：

  5-羟基-3-甲基-3H-1-苯并呋喃-2-酮 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 66.0h， 生成 5-benzyloxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran-2-one
  参考文献：
  名称：

  Syntheses of Tetrahydrofurobenzofurans and Dihydromethanobenzodioxepines from 5-Hydroxy-3-methyl-3H-benzofuran-2-one. Rearrangement and Ring Expansion under Reductive Conditions on Treatment with Hydrides

  摘要：

  5-Hydroxy-3-methyl-3H-benzofuran-2-one, 5, easily obtained from pyruvic acid and 1,4-cyclohexanedione, was used as a starting material to prepare ()-5-hydroxy-3a-methyl-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran, 10, and ()-7-hydroxy-5-methyl-4,5-dihydro-2,5-methano-1,3-benzodioxepine, 14. Reduced reactivity relative to 5-hydroxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran2-one, 6, was preliminarily studied. Meanwhile, a plausible mechanism with regard to the formation of 10 and 14, which included cyclization, rearrangement, and ring expansion of hemiacetal, 15, is proposed. Specific carbamates of phenols, 10 and 14, have shown impressive inhibitory activities against human acetyleholinesterase (AChE) and butyrylcholinesterase (BChE) ex vivo.

  DOI：

  10.1021/jo0503052

文献信息

• Syntheses of Tetrahydrofurobenzofurans and Dihydromethanobenzodioxepines from 5-Hydroxy-3-methyl-3<i>H</i>-benzofuran-2-one. Rearrangement and Ring Expansion under Reductive Conditions on Treatment with Hydrides
  作者：Weiming Luo、Qian-sheng Yu、Harold W. Holloway、Damon Parrish、Nigel H. Greig、Arnold Brossi

  DOI：10.1021/jo0503052

  日期：2005.8.1

  5-Hydroxy-3-methyl-3H-benzofuran-2-one, 5, easily obtained from pyruvic acid and 1,4-cyclohexanedione, was used as a starting material to prepare ()-5-hydroxy-3a-methyl-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran, 10, and ()-7-hydroxy-5-methyl-4,5-dihydro-2,5-methano-1,3-benzodioxepine, 14. Reduced reactivity relative to 5-hydroxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran2-one, 6, was preliminarily studied. Meanwhile, a plausible mechanism with regard to the formation of 10 and 14, which included cyclization, rearrangement, and ring expansion of hemiacetal, 15, is proposed. Specific carbamates of phenols, 10 and 14, have shown impressive inhibitory activities against human acetyleholinesterase (AChE) and butyrylcholinesterase (BChE) ex vivo.