1-(2-furyl)-4-methyl-1-penten-3-one | 4196-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-(2-furyl)-4-methyl-1-penten-3-one
• 英文别名: 1-furan-2-yl-4-methyl-pent-1-en-3-one；1t-[2]furyl-4-methyl-pent-1-en-3-one；1t-[2]Furyl-4-methyl-pent-1-en-3-on；(E)-1-(furan-2-yl)-4-methylpent-1-en-3-one
• CAS: 4196-97-8
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: VYMFKEHZNHXQIN-AATRIKPKSA-N

物化性质

• 沸点：
  101-102 °C(Press: 5 Torr)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-furyl)-4-methyl-1-penten-3-one 在 Wilkinson's catalyst 氢气 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、220.64 kPa 条件下， 反应 28.33h， 生成 5-(2-Furan-2-yl-ethyl)-5-hydroxy-6-methyl-3-oxo-heptanoic acid methyl ester
  参考文献：
  名称：

  4-Hydroxy-5,6-dihydropyrones as Inhibitors of HIV Protease:  The Effect of Heterocyclic Substituents at C-6 on Antiviral Potency and Pharmacokinetic Parameters

  摘要：

  Due largely to the emergence of multi-drug-resistant HIV strains, the development of new HIV protease inhibitors remains a high priority for the pharmaceutical industry. Toward this end, we previously identified a 4-hydroxy-5,6-dihydropyrone lead compound (CI-1029, 1) which possesses excellent activity against the protease enzyme, good antiviral efficacy in cellular assays, and promising bioavailability in several animal species. The search for a suitable backup candidate centered on the replacement of the aniline moiety at C-6 with an appropriately substituted heterocyle. In general, this series of heterocyclic inhibitors displayed good activity (in both enzymatic and cellular tests) and-low cellular toxicity; furthermore, several analogues exhibited improved pharmacokinetic parameters in animal models. The compound with the best combination of high potency, low toxicity, and favorable bioavailabilty was (S)-3-(2-tertbutyl-4-hydroxymethy1- 5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (13-(S)). This thiophene derivative also exhibited excellent antiviral efficacy against mutant HIV protease and resistant HIV strains. For these reasons, compound 13-(S) was chosen for further preclinical evaluation.

  DOI：

  10.1021/jm0003844
• 作为产物：
  描述：

  糠醛 、 3-甲基-2-丁酮 生成 1-(2-furyl)-4-methyl-1-penten-3-one
  参考文献：
  名称：

  关于呋喃化合物的开环反应。四、糠醛与甲基丙基酮、甲基异丙基酮和频那可林碱的缩合产物

  摘要：

  甲基丙基酮与糠醛在酮的α-甲基和α-亚甲基上通过碱缩合，得到较大比例的1-(2-呋喃基)-1-己烯-3-酮(I)和3-乙基-4-(2-furyl)-3-buten-2-one (II) 的比例要小得多。前者的糠基酮（I）在乙醇盐酸中开环生成γ，ζ-二氧癸酸（III），后者（II）被次氯酸钠氧化生成α-乙基-2-呋喃丙烯酸（IV） . 糠基甲基异丙基酮 (V) 和糠基甲基叔丁酮 (VI) 在盐酸醇中开环得到 γ, ζ-二氧代-η-甲基壬酸 (VII) 和 γ, ζ-二氧代-η, η-二甲基壬酸酸（VIII）。

  DOI：

  10.1246/bcsj.27.143

文献信息

• A general convenient synthesis of conjugated dieneynes
  作者：Iwona Maciągiewicz、Piotr Dybowski、Aleksandra Skowrońska

  DOI：10.1016/s0022-328x(01)01275-x

  日期：2002.2

  A convenient synthesis of dieneynes 1 is described. Our strategy involves reaction of readily available thiophosphates with sodium acetylides, in which new single and double carbon–carbon bonds are formed.

  描述了二烯酮1的方便合成。我们的策略涉及容易获得的硫代磷酸酯与乙炔酸钠的反应，在其中形成新的单碳和双碳-碳键。
• On the Ring-opening Reactions of the Furan Compounds. IV. The Condensation Products of Furfural with Methyl Propyl Ketone, Methyl Isopropyl Ketone and Pinacolin by Alkali
  作者：Hiroshi Midorikawa

  DOI：10.1246/bcsj.27.143

  日期：1954.3

  Methyl propyl ketone condensed with furfural by alkali both at the α-methyl and α-methylene groups of the ketone, giving 1-(2-furyl)-1-hexen-3-one (I) in a larger proportion and 3-ethyl-4-(2-furyl)-3-buten-2-one (II) in a much smaller proportion. The former furfurylidene ketone (I) gave γ, ζ-dioxocapric acid (III) on the ring-opening in alcoholic hydrochloric acid, and the latter (II) was oxidized

  甲基丙基酮与糠醛在酮的α-甲基和α-亚甲基上通过碱缩合，得到较大比例的1-(2-呋喃基)-1-己烯-3-酮(I)和3-乙基-4-(2-furyl)-3-buten-2-one (II) 的比例要小得多。前者的糠基酮（I）在乙醇盐酸中开环生成γ，ζ-二氧癸酸（III），后者（II）被次氯酸钠氧化生成α-乙基-2-呋喃丙烯酸（IV） . 糠基甲基异丙基酮 (V) 和糠基甲基叔丁酮 (VI) 在盐酸醇中开环得到 γ, ζ-二氧代-η-甲基壬酸 (VII) 和 γ, ζ-二氧代-η, η-二甲基壬酸酸（VIII）。
• Furfural derivatives as a vehicle
  申请人：RHODIA OPERATIONS

  公开号：US20160000066A1

  公开（公告）日：2016-01-07

  The present invention concerns the use of a furfural derivative of formula (I) in which R represents (i) a —CH═CR′ 1 —COR 1 group, a group a group a group or a —CHO and R′ represents a hydrogen atom or a (C 1 -C 4 )alkyl group, as a chemical vehicle, as a solvent, co-solvent, coalescing agent, crystallization inhibitor, plasticising agent, degreasing agent, etchant, cleaning agent or agent for increasing biological activity, and more particularly as a solvent. It also concerns phytosanitary formulations or resin-solubilising formulations comprising at least one such furfural derivative of formula (I).

  本发明涉及将式(I)中R代表(i) -CH═CR′1-COR1基团，一个基团，一个基团，或-CHO，R′代表氢原子或(C1-C4)烷基基团的糠醛衍生物用作化学载体、溶剂、共溶剂、凝聚剂、结晶抑制剂、增塑剂、脱脂剂、蚀刻剂、清洁剂或增加生物活性的剂，更特别地作为溶剂。还涉及包含至少一种上述式(I)的糠醛衍生物的植物保健配方或树脂溶解配方。
• HIV protease inhibitors
  申请人：Warner-Lambert Company

  公开号：US06528510B1

  公开（公告）日：2003-03-04

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.

  本发明涉及具有改进药理特性的新型带有连环杂环的二氢吡喃，能有效抑制HIV天冬氨酸蛋白酶，阻断HIV的感染性。这些二氢吡喃在开发治疗病毒感染和疾病，包括艾滋病的疗法方面是有用的。本发明还涉及合成这些二氢吡喃的方法，以及在制备最终化合物中有用的中间体。
• Cyclodimerization of<i>α</i>,<i>β</i>-Unsaturated Ketones Catalyzed by Lanthanoid Tri-2-propoxides
  作者：Tamon Okano、Katsutoshi Ohno、Jitsuo Kiji

  DOI：10.1246/cl.1996.1041

  日期：1996.12

  α,β-Unsaturated ketones are cyclodimerized by the catalysis of lanthanoid tri-2-propoxides into substituted cyclohexanones in good yields. The catalytic activity of the lanthanoids is fairly superior to those of the sodium or aluminum propoxides.

  在镧系三-2-丙氧基化合物的催化作用下，α、β-不饱和酮可以环二聚化成取代的环己酮，而且产量很高。类苋菜酮的催化活性比丙氧基化钠或铝的催化活性要强得多。