4-hydroxy-3-[1'-(m-nitrophenyl)prop-2'-en-1'-yl]-5-spirocyclohexyl-[5H]furan-2-one | 676321-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-3-[1'-(m-nitrophenyl)prop-2'-en-1'-yl]-5-spirocyclohexyl-[5H]furan-2-one
• 英文别名: 4-Hydroxy-3-[1-(3-nitrophenyl)prop-2-enyl]-1-oxaspiro[4.5]dec-3-en-2-one
• CAS: 676321-22-5
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: ZJPSDVANDYPDNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 4-hydroxy-3-[1'-(m-nitrophenyl)prop-2'-en-1'-yl]-5-spirocyclohexyl-[5H]furan-2-one 在 diethylzinc 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 以35%的产率得到4-hydroxy-3-[cyclopropyl-(m-nitrophenyl)methyl]-5-spirocyclohexyl-[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
• 作为产物：
  描述：

  4-(m-nitrocinnamyloxy)-1-oxaspiro[4.5]dec-3-en-2-one 在 Yt(OTf)3 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以94%的产率得到4-hydroxy-3-[1'-(m-nitrophenyl)prop-2'-en-1'-yl]-5-spirocyclohexyl-[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

• Microwave-accelerated Claisen rearrangements of allyl tetronates and tetramates
  作者：Rainer Schobert、Gary J. Gordon、Gillian Mullen、Ralf Stehle

  DOI：10.1016/j.tetlet.2003.12.024

  日期：2004.2

  [3,3]-Sigmatropic rearrangements of allyl tetronates and allyl tetramates to give 3-allyltetronic or -tetramic acids, respectively, proceed within 20–60 min under microwave irradiation (300 W, 130–190 °C). Consecutive (homo)sigmatropic [1,5] H-shifts such as oxa-ene reactions are promoted less effectively, which allows the isolation of Claisen intermediates of sigmatropic domino sequences, in contrast

  [3,3]四烯丙基四烯酸酯和四烯丙基烯丙酸酯的[3,3]-正离子重排分别在微波辐射（300 W，130-190°C）下在20–60分钟内进行，生成3-烯丙基电子或-丁酸。连续的（同质）共生性[1,5] H-位移（例如氧杂-烯反应）被不太有效地促进，与常规加热相比，它可以分离出具有生性多米诺骨牌序列的克莱森中间体。