2-acetyl-3,4,4-trimethyl-2-buten-4-olide | 13156-10-0

• 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: 2-acetyl-3,4,4-trimethyl-2-buten-4-olide
• 英文别名: 3-acetyl-4,5,5-trimethylfuran-2(5H)-one；2(5H)-Furanone, 3-acetyl-4,5,5-trimethyl-；3-acetyl-4,5,5-trimethylfuran-2-one
• CAS: 13156-10-0
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: FKCLNCHKLVJVFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-3,4,4-trimethyl-2-buten-4-olide 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以60.7%的产率得到2-Acetyl-3-methyl-4,4-dimethyl-2-buten-4-olide oxime
  参考文献：
  名称：

  Recyclization and photorearrangements of 2-acetyl-4,4-dialkyl-2-buten-4-olide oximes

  摘要：

  DOI：

  10.1007/bf00479901
• 作为产物：
  描述：

  D,L-2,3-di<4,5,5-trimethyl-2(2H)-oxo-3-furyl>-2,3-butanediol 在 lead(IV) acetate 作用下， 生成 2-acetyl-3,4,4-trimethyl-2-buten-4-olide
  参考文献：
  名称：

  Avetisyan, A. A.; Margaryan, A. Kh.; Gukasyan, O. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 516 - 519

  摘要：

  DOI：

文献信息

• Unsaturated lactones. LXXIII. Synthesis and antiviral activity of some substituted 2-buten-4-olides
  作者：A. A. Avetisyan、A. N. Dzhandzhapanyan、R. G. Nazaryan、V. I. Votyakov、S. V. Khlyustov、G. V. Vladyko、V. Ya. Klimovich、L. V. Korobchenko、M. N. Shashikhina、S. V. Zhavrid

  DOI：10.1007/bf00759749

  日期：1982.6

  spectrum of biological activity. Methods have been developed [12-16] for the preparation of substituted 2-buten-4-olides with a variety of function&l substituents. In order to obtain new compounds containing the 2-buten-4-olide ring and to examine their antiviral activity, we have carried out some chemical reactions of 2-acyl derivatives of 2-buten-4-olides (I-III), in whichthe lactone ring is conserved, as

  已知 [i-ii] 含有内酯环的化合物（合成的和天然来源的）具有相当广泛的生物活性。已开发出制备具有多种功能和1 取代基的取代的 2-丁烯-4-内酯的方法 [12-16]。为了获得含有 2-buten-4-olides 环的新化合物并检验它们的抗病毒活性，我们对 2-buten-4-olides (I-III) 的 2-acyl 衍生物进行了一些化学反应，在其中内酯环是保守的，如下：
• Efficient synthesis of new butenolides by subsequent reactions: application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones
  作者：Nawel Cheikh、Nathalie Bar、Nourredine Choukchou-Braham、Bachir Mostefa-Kara、Jean-François Lohier、Jana Sopkova、Didier Villemin

  DOI：10.1016/j.tet.2010.12.062

  日期：2011.2

  We have developed the synthesis of twenty four new iminolactones, bis-iminolactones and bis-lactones by subsequent esterification–condensation or addition–condensation reactions according to two strategies from α-hydroxyketones. The X-ray diffraction data of a bis-iminolactone is described and present an interesting helical column packing.

  根据α-羟基酮的两种策略，我们通过随后的酯化-缩合或加成-缩合反应，开发了二十四种新的亚氨基内酯，双亚氨基内酯和双内酯。描述了双亚氨基内酯的X射线衍射数据，并给出了令人感兴趣的螺旋柱填料。
• Discovery of 5-(5,5-Dimethylbutenolide-3-ethylidene)-2-amino-imidazolinone Derivatives as Fungicidal Agents
  作者：Bo Tang、Mingyan Yang、Yu Zhao、Lingqing Kong、Weiwei Wang、Mingan Wang

  DOI：10.3390/molecules200813740

  日期：——

  The novel fungicidal agents 5-(5,5-dimethylbutenolide-3-ethylidene)-2-amino-imidazolinone derivatives, were designed and synthesized in moderate to excellent yields in four steps by αa-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS and 1H-NMR. The preliminary bioassay showed that some of these compounds, such as 4a, 4e and 5g exhibit 94.9%, 92.8% and 81.4% inhibition rates against Sclerotinia scleotiorum at the concentration of 50 µg/mL, respectively. The EC50 values of compounds 4e and 4i were 4.14 and 3.27 µM against Alternaria Solani, and 5g had EC50 value of 3.23 µM against S. scleotiorum. Compounds 4d and 4g displayed 98.0% and 97.8% control of spore germination against Botrytis cinerea at the concentration of 100 µg/mL, respectively.

  设计合成了新型杀菌剂5-(5，5-二甲基丁烯内酯-3-亚乙基)-2-氨基-咪唑啉酮衍生物，以αa-羟基酮和双烯酮为原料，通过四步反应以中等至优异的产率合成，并通过HR-ESI-MS和1H-NMR进行表征。初步生物测定结果表明：一些化合物（例如4a、4e和5g）对核盘菌的抑制率分别为94.9%、92.8%和81.4%，浓度为50 µg/mL；化合物4e和4i对早疫病菌的EC50值分别为4.14和3.27 μM；化合物5g对核盘菌的EC50值为3.23 μM；化合物4d和4g对灰霉病菌孢子萌发的控制率分别为98.0%和97.8%，浓度均为100 µg/mL。
• Cyclocondensation of 3-acetylfuran-2(5H)-ones with benzylidenemalononitrile. Synthesis of 3-(5-amino-4,6-dicyanobiphenyl-3-yl)furan-2(5H)-ones
  作者：R. M. Hakobyan、S. S. Hayotsyan、G. S. Melikyan

  DOI：10.1134/s1070428015120313

  日期：2015.12

  In particular, furan-2(5H)-one derivatives containing nonidentical aromatic substituents in positions 3 and 4 of the furan ring exhibit various biological activities [1]. An example is the anti-inflammatory drug Rofecoxib [4-(4-methanesulfonylphenyl)-3-phenylfuran-2(5H)-one]. Eutypoid A isolated from the marine mangrove fungus Eutypa sp. (# 424) [2] and gymnoascolides [3] isolated from the Australian

  3,4-二取代的furan-2(5H)-one 片段存在于许多天然生物活性化合物中。特别是在呋喃环的 3 位和 4 位含有不同芳族取代基的 furan-2(5H)-one 衍生物表现出各种生物活性 [1]。一个例子是抗炎药罗非昔布[4-(4-甲磺酰基苯基)-3-苯基呋喃-2(5H)-one]。Eutypoid A 从海洋红树林真菌 Eutypa sp. 中分离出来。(# 424) [2] 和从澳大利亚土壤子囊菌 Gimnoascus reessii 和 Malbranchea filamentosa IFM41300 中分离出来的裸蚴类动物 [3] 是天然存在的 3,4-二取代呋喃-2(5H)-ones。我们以前 [4-8] 合成了在内酯环的 3 位带有杂芳族取代基的不饱和 γ-内酯，并揭示了苯并咪唑基-、苯并噻唑基-、和苯并恶唑基取代的呋喃-2-酮。在本文中，我们报道了在 C 上含有 5-氨基-4
• Versatile Synthesis of Acylfuranones by Reaction of Acylketenes with α-Hydroxy Ketones: Application to the One-Step Multicomponent Synthesis of Cadiolide B and Its Analogues
  作者：Philippe Alexandre Peixoto、Agathe Boulangé、Stéphane Leleu、Xavier Franck

  DOI：10.1002/ejoc.201300166

  日期：2013.6

  Functionalized acylfuranones have been prepared in a one-step procedure by thermal fragmentation of the corresponding dioxinones in the presence of hydroxy ketones in basic conditions. Multicomponent reactions also occur on addition of an aldehyde as a third reaction partner resulting in an expeditious access to cadiolide B and its analogues.

  在碱性条件下，在羟基酮的存在下，通过相应的二恶英酮的热裂解，以一步法制备了官能化的酰基呋喃酮。添加醛作为第三个反应伙伴时也会发生多组分反应，从而快速获得卡地内酯 B 及其类似物。