3-phenyl-5-methyl-2,5-dihydrofuran-2-one | 55091-68-4

• 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: 3-phenyl-5-methyl-2,5-dihydrofuran-2-one
• 英文别名: 5-methyl-3-phenyl-2(5H)-furanone；5-methyl-3-phenylfuran-2(5H)-one；2-methyl-4-phenylfuranone；5-methyl-3-phenyl-5H-furan-2-one；5-Methyl-3-phenyl-5H-furan-2-on；2-methyl-4-phenyl-2H-furan-5-one
• CAS: 55091-68-4
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: GVGXBYFGDYETKS-UHFFFAOYSA-N

物化性质

• 熔点：
  52-52.5 °C(Solv: ethanol, 75% (64-17-5))
• 沸点：
  353.9±31.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-5-methyl-2,5-dihydrofuran-2-one 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以5.3 g的产率得到1-phenyl-4-methyl-3,6-dioxabicyclo<3.1.0>hexan-2-one
  参考文献：
  名称：

  Caus, Maria J.; Cerfontain, Hans; Piniella, Juan F., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, p. 515 - 519

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基-4-苯基戊-2-酮 在 sodium tetrahydroborate 、 正丁基锂 、 溶剂黄146 、 二异丙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.75h， 生成 3-phenyl-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Small Changes Result in Large Differences: Discovery of (−)-Incrustoporin Derivatives as Novel Antiviral and Antifungal Agents

  摘要：

  On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in vivo. The small changes between 4 and 5 at the 3,4-position result in large differences in bioactivities. Compounds 4 exhibited significantly higher antiviral activity against tobacco mosaic virus (TMV) than dehydro compounds 5. However, the antifungal activity of 4 is relatively lower than that of 5. Compounds 4a, 4c, and 4i with excellent in vivo anti-TMV activity emerged as new antiviral lead compounds. Compounds 5d-g showed superiority over the commercial fungicides chlorothalonil and carbendazim against Cercospora arachidicola Hor at 50 mg kg(-1). The present study provides fundamental support for the development and optimization of (-)-incrustoporin derivatives as potential inhibitors of plant virus and pathogenic fungi.

  DOI：

  10.1021/jf503060k

文献信息

• Alpha,beta-unsaturated esters and acids by stereoselective dehydration
  申请人：Deng Xiaohu

  公开号：US20060004195A1

  公开（公告）日：2006-01-05

  There are provided by the present invention certain pyrazole based CCK-1 receptor modulators which have the general formula: wherein Ar is an aromatic or heteroaromatic group, X is a hydrocarbon linker, Y is a bond or hydrocarbon linker and R 1 , R 2 , R 3 , R 4 and R 5 are certain organic substituents, methods for making the same, and stereoselective dehydration methods for generally making α,β-unsaturated esters, acids and their derivatives.

  本发明提供了一些基于吡唑的CCK-1受体调节剂，其具有以下一般式： 其中Ar是芳香族或杂环芳基，X是碳氢链，Y是键或碳氢链，R1、R2、R3、R4和R5是某些有机取代基，以及制备这些化合物的方法，以及用于通常制备α，β-不饱和酯，酸及其衍生物的立体选择性脱水方法。
• The Mukaiyama reaction of ketene bis(trimethylsilyl) acetals with α-halo acetals
  作者：F.W.J. Demnitz

  DOI：10.1016/s0040-4039(01)93317-9

  日期：——

  Ketene bis(trimethylsilyl) acetals were reacted with α-halo acetals giving β-alkoxy-γ-halo acids which were converted to butenolides by reaction with two equivalents of base. This constitutes a novel and short butenolide synthesis.

  使乙烯酮双（三甲基甲硅烷基）乙缩醛与α-卤代乙缩醛反应，得到β-烷氧基-γ-卤代酸，通过与两当量的碱反应将其转化为丁烯化物。这构成了新颖且短的丁烯内酯合成。
• Butenolide Synthesis from Functionalized Cyclopropenones
  作者：Sean S. Nguyen、Andrew J. Ferreira、Zane G. Long、Tyler K. Heiss、Robert S. Dorn、R. David Row、Jennifer A. Prescher

  DOI：10.1021/acs.orglett.9b03298

  日期：2019.11.1

  A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst

  报道了由羟甲基环丙烯酮合成取代的丁烯化物的一般方法。功能化的环丙烯酮与催化量的膦进行开环反应，形成反应性乙烯酮。这些中间体可以被羟基侧基捕获，以提供目标丁烯酸内酯支架。该反应在各种溶剂中且催化剂负载量低时有效进行。重要的是，环化耐受广泛的官能团，产生各种α-和γ-取代的丁烯内酯。
• A general method for the preparation of carbonyl compounds and butenolides from organomanganese pentacarbonyl complexes
  作者：Philip. DeShong、Daniel R. Sidler、Philip J. Rybczynski、Greg A. Slough、Arnold L. Rheingold

  DOI：10.1021/ja00216a034

  日期：1988.4

  La reaction des complexes pentacarbonyles d'alkylmanganese avec divers composes ethyleniques et acetyleniques donne des cetones et des dihydro-2,5 furannones-2

  La 反应 des complexes pentacarbonyles d'alkylmanganese avec divers composes Etheniques et acetyleniques donne des cetones et des dihydro-2,5 furannones-2
• Microwave Assisted Suzuki Reactions for the Preparation of the Antifungal 3-Aryl-5-methyl-2,5-dihydrofuran-2-ones
  作者：Paul A. Worthington、Christopher J. Mathews、John Taylor、Melloney J. Tyte

  DOI：10.1055/s-2005-862367

  日期：——

  The Suzuki cross-coupling reaction of arylboronic acids with a bromo-furanone has been developed to prepare a series of substituted 2,5-dihydrofuran-2-ones related to the fungal metabolite, incrustoporin. A protocol of microwave heating was introduced to improve synthesis throughput.

  已开发了芳基硼酸与溴吡喃酮的铃木交叉耦合反应，以合成一系列与真菌代谢物incrustoporin相关的取代2,5-二氢呋喃-2-酮。引入了一种微波加热的方案，以提高合成效率。