5-isopropoxyfuran-2(5H)-one | 98272-45-8

• 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: 5-isopropoxyfuran-2(5H)-one
• 英文别名: 2-propan-2-yloxy-2H-furan-5-one
• CAS: 98272-45-8
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: JXWQEQNPOGXZNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  5-isopropoxyfuran-2(5H)-one 在 硫酸 作用下， 生成 4-(diethoxymethyl)-5,5-dimethyltetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones

  摘要：

  In this work we report a versatile synthesis of fourteen gamma-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 mu mol L-1). In general, alpha,beta-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76% of inhibition in 1000 mu mol L-1. The results indicate that regardless of saturation, the presence of the gamma-lactone moiety is important for the bioactivity, but their presence has no implications with potency.

  DOI：

  10.1590/s0103-50532012001200016
• 作为产物：
  描述：

  5-羟基呋喃-2(5H)-酮 、 异丙醇 反应 72.0h， 以68%的产率得到5-isopropoxyfuran-2(5H)-one
  参考文献：
  名称：

  5-烷氧基-2（5H）-呋喃酮的催化动力学拆分

  摘要：

  使用手性氨基醇催化芳基硫醇的1,4-加成反应，研究了外消旋5-烷氧基-2（5H）-呋喃酮的动力学拆分。使用各种丁烯内酯表明，γ-烷氧基取代基似乎对于达到高对映选择性是必不可少的，而芳基硫醇中的供电子取代基也增加了选择性。金鸡纳生物碱是用于动力学拆分的优选催化剂，奎宁和奎尼丁导致最有效和选择性的硫醇添加。观察到显着的稀释效果和对反应物添加方式的强烈依赖性。优化研究提出了动力学解析的5-甲氧基-2（5H）-呋喃酮2导致（R）-2或（S）-2对映体过量超过90％。给出了奎宁（奎尼丁）催化动力学拆分的机理。

  DOI：

  10.1016/s0040-4020(01)85016-x

文献信息

• Singlet oxygen photooxygenation of furans
  作者：Klaus Gollnick、Axel Griesbeck

  DOI：10.1016/s0040-4020(01)96576-7

  日期：1985.1

  the corresponding ozonides as the primary products of (4+2)-cycloadditions of singlet oxygen to these furans. However, reactions of the alcohols with the ozonides are too fast to allow the ozonides to be isolated. Instead, the same products are obtained as are isolated from reactions carried out by dissolving the ozonides in the alcohols. Depending on the structure of the ozonide, three pathways are

  呋喃（四苯基卟吩的-光敏氧合19），2-甲基呋喃（26），2-乙基呋喃（39），糠醇（24），2-乙酰基呋喃（40），2- methoxyfuran（42），2,5-二甲基呋喃（30），非极性非质子溶剂中的糠醛（25）和5-甲基糠醛（41）由于将单线态氧（4 + 2）-环加成到这些呋喃中而产生相应的单体不饱和仲臭氧化合物。除源自25的臭氧化物外，分离并表征了臭氧化物（1 H-和13 C- NMR。光谱等）。在非极性非质子溶剂中，臭氧化物衍生自19，26和39经历热重排为相应的顺式-diepoxides和epoxylactones。臭氧化物31，衍生自30，但是，二聚化，仅在高于约60℃是一个顺式-diepoxide从任一形成31或其二聚体。醇（MeOH，EtOH，i-PrOH）中呋喃的玫瑰孟加拉光敏加氧也​​产生相应的臭氧化物，这些化合物是单重态氧向这些呋喃的（4 + 2）-环加成的主要产
• Toxicity and Sublethal Effects of Phthalides Analogs to<i>Rhyzopertha dominica</i>
  作者：Elizeu S. Farias、Tamíris A. Araújo、Gabriela C. Resende、Júlia N. D. Campos、Mirian F. Pimentel、Elson S. Alvarenga、Marcelo C. Picanço

  DOI：10.1002/cbdv.201800557

  日期：2019.3

  efficacious phthalides 15 and 17. Compound 15 presented the lowest LD50 (1.97 μg g−1), being four times more toxic than Bifenthrin® (LD50=9.11 μg g−1). Both compounds presented an LT50 value equal to 24 h. When applied at a sublethal dose, both phthalides (especially compound 15), reduced the emergence of the first progeny of R. dominica. These findings highlight the potential of phthalides 15 and 17

  邻苯二甲酸酯及其前体已证明具有多种生物活性。合成了 18 种苯酞，并在储粮害虫 Rhyzopertha dominica 上进行了测试。在筛选生物测定中，化合物 rac-(2R,2aS,4R,4aS,6aR,6bS,7R)-7-bromohexahydro-2,4-methano-1,6-dioxacyclopenta[cd]pentalen-5(2H)-one (15) 和 rac-(3R,3aR,4R,7S,7aS)-3-(propan-2-yloxy)hexahydro-4,7-methano-2-benzofuran-1(3H)-one (17) 显示死亡率类似于商业杀虫剂联苯菊酯® (≥90 %)。对于最有效的邻苯二酚 15 和 17，确定了杀死 50% 多米尼克红藻种群所需的时间 (LT50) 和剂量 (LD50)。化合物 15 的 LD50 最低 (1.97 μg g-1)，是其四倍毒性高于联苯菊酯
• Chiral induction in photochemical reactions - 15.
  作者：Norbert Hoffmann、Helmut Buschmann、Gerhard Raabe、Hans-Dieter Scharf

  DOI：10.1016/s0040-4020(01)89419-9

  日期：1994.1

  The mechanism of the diastereoselection in the photosensitized [2 + 2]-cycloaddition reaction of ethylene to 5-alkoxy-2(5H)-furanones is investigated. The dependence of product ratio on the reaction temperature as well as on structural features of the enone system is measured. The structure dependent activation parameter differences (Delta Delta H-#, Delta Delta S-#) obtained by this method (modified Eyring plot) are used as a tool to characterize the stereoelectronic factors, which are responsible for the diastereoselection. In detail these factors involve: pyramidalization of the beta-carbon, homoanomeric effect, and the steric requirements of the alkoxy substituent in the relaxed ((3) pi pi*)-excited furanones.
• Isolation and stereochemical assignment of phthalides resulting from the Diels–Alder reaction between 5-isopropoxyfuran-2(5H)-one and cyclopentadiene
  作者：G.C. Resende、E.S. Alvarenga、P.H. Willoughby

  DOI：10.1016/j.molstruc.2015.08.028

  日期：2015.12
• DE875650
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