(S)-5-methyl-4-benzyloxy-[5H]furan-2-one | 1071501-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-5-methyl-4-benzyloxy-[5H]furan-2-one
• 英文别名: (2S)-2-methyl-3-phenylmethoxy-2H-furan-5-one
• CAS: 1071501-60-4
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: JCSBFABPKABOBN-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-methyl-4-benzyloxy-[5H]furan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到(S)-γ-methyltetronic acid
  参考文献：
  名称：

  Tipranavir analogous 3-sulfonylanilidotetronic acids: new synthesis and structure-dependent anti-HIV activity

  摘要：

  Sulfonamide-containing tetronic acids 1, structural analogues of the HIV-1 protease inhibitor tipranavir, were synthesised in five steps including a microwave-assisted Claisen rearrangement of cinnamyl tetronates and a modified Charette cyclopropanation of the so-formed 3-allyltetronic acids. Compounds 1 with two non-H residues (R-1, R-2) at C-5 of the tetronate core exhibited structure-dependent antiviral activity in two HIV strains. Derivatives 1c (R-1=R-2=Me, R-3=Cl) and 1d (R-1,R-2=(CH2)(5,) R-3=Me) were most active (IC50<10 mu M) in the sensitive strain HIVNL4-3. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.094
• 作为产物：
  描述：

  (三苯基膦烯)乙烯酮 、 苄基2-羟基丙酸酯 在 苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以62%的产率得到(S)-5-methyl-4-benzyloxy-[5H]furan-2-one
  参考文献：
  名称：

  Tipranavir analogous 3-sulfonylanilidotetronic acids: new synthesis and structure-dependent anti-HIV activity

  摘要：

  Sulfonamide-containing tetronic acids 1, structural analogues of the HIV-1 protease inhibitor tipranavir, were synthesised in five steps including a microwave-assisted Claisen rearrangement of cinnamyl tetronates and a modified Charette cyclopropanation of the so-formed 3-allyltetronic acids. Compounds 1 with two non-H residues (R-1, R-2) at C-5 of the tetronate core exhibited structure-dependent antiviral activity in two HIV strains. Derivatives 1c (R-1=R-2=Me, R-3=Cl) and 1d (R-1,R-2=(CH2)(5,) R-3=Me) were most active (IC50<10 mu M) in the sensitive strain HIVNL4-3. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.094

文献信息

• Tipranavir analogous 3-sulfonylanilidotetronic acids: new synthesis and structure-dependent anti-HIV activity
  作者：Rainer Schobert、Ralf Stehle、Hauke Walter

  DOI：10.1016/j.tet.2008.07.094

  日期：2008.9

  Sulfonamide-containing tetronic acids 1, structural analogues of the HIV-1 protease inhibitor tipranavir, were synthesised in five steps including a microwave-assisted Claisen rearrangement of cinnamyl tetronates and a modified Charette cyclopropanation of the so-formed 3-allyltetronic acids. Compounds 1 with two non-H residues (R-1, R-2) at C-5 of the tetronate core exhibited structure-dependent antiviral activity in two HIV strains. Derivatives 1c (R-1=R-2=Me, R-3=Cl) and 1d (R-1,R-2=(CH2)(5,) R-3=Me) were most active (IC50<10 mu M) in the sensitive strain HIVNL4-3. (C) 2008 Elsevier Ltd. All rights reserved.