2-Phenacyl-5-methylfuran | 117203-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Phenacyl-5-methylfuran
• 英文别名: 2-(5-methylfuran-2-yl)-1-phenylethan-1-one；2-(5-methylfuran-2-yl)-1-phenylethanone
• CAS: 117203-31-3
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: KBLQALSRUIXEGP-UHFFFAOYSA-N

物化性质

• 沸点：
  115 °C(Press: 0.1 Torr)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2-Phenacyl-5-methylfuran 在 氧气 、 亚甲兰 、 二甲基硫 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2-substituted furans: Application to the biomimetic synthesis of merrekentrone C

  摘要：

  (β-酮)-2-取代呋喃的光氧化反应在一步法操作中，以良好至优异的产率得到功能化的3(2H)-呋喃酮。这一方法被应用于短小且仿生的倍半萜烯merrekentrone C的合成中的关键步骤。merrekentrone C的前体，酮二呋喃，是通过在Fenton型条件下，α-碘代-3-乙酰基呋喃与烯基呋喃的交叉偶联反应来合成的。

  DOI：

  10.1039/c1ob05567d
• 作为产物：
  描述：

  (5-Methyl-2-furyl)dibenzoylmethane 在 氢氧化钾 作用下， 以 乙醚 、 水 为溶剂， 反应 4.0h， 以95%的产率得到2-Phenacyl-5-methylfuran
  参考文献：
  名称：

  Antonioletti, Roberto; Bonadies, Francesco; Prencipe, Teresa, Gazzetta Chimica Italiana, 1988, vol. 118, # 9, p. 629 - 632

  摘要：

  DOI：

文献信息

• Synthesis of pyrazolylvinyl ketones from furan derivatives
  作者：Nattawut Sawengngen、Petrakis N. Chalikidi、Sara Araby、Frank Hampel、Peter Gmeiner、Olga V. Serdyuk

  DOI：10.1039/c9ob00701f

  日期：——

  A new protocol for the synthesis of pyrazol-5-ylvinyl ketones, e.g. pyrazole-chalcones, employing furfuryl ketones as a triketone equivalent, has been developed. The reaction occurs under mild conditions and does not require the use of expensive materials. Other important benefits include the simplicity and atom efficiency of this approach.

  已经开发了使用糠基酮作为三酮等同物来合成吡唑-5-基乙烯基酮，例如吡唑-查耳酮的新方案。该反应在温和的条件下进行，不需要使用昂贵的材料。其他重要的好处包括这种方法的简单性和原子效率。
• A new convinient synthesis of 3(2H)-furanones
  作者：R Antonioletti、F Bonadies、A Scettri

  DOI：10.1016/s0040-4039(00)96106-9

  日期：1987.1

  A selective oxidative fission of the heterocyclic nucleus of 5-methyl-2-(acylmethyl)furans or 2-(5-methyl-2-furyl)-1,3-dicarbonyl compounds by m-chloroperbenzoic acid allows the easy synthesis of the 3(2H)-furanone system.

  间氯过苯甲酸对5-甲基-2-（酰基甲基）呋喃或2-（5-甲基-2-呋喃基）-1,3-二羰基化合物的杂环核进行选择性氧化裂变，可轻松合成3 （2H）-呋喃酮体系。
• Synthesis of Isoxazolylvinyl Ketones from Substituted Furans
  作者：Olga V. Serdyuk、Frank Hampel、Vladimir T. Abaev

  DOI：10.1007/s10593-020-02841-y

  日期：2020.11

  the preparation of isoxazolylvinyl ketones related to potential cytotoxic agents has been developed. In the first step, the reaction of furfuryl ketones with hydroxylamine hydrochloride affords the corresponding oximes. Further, the oxidative ring opening – ring closure reaction of oximes leads to isoxazoles with an α, β-unsaturated carbonyl motif. The developed procedure is metal-free and does not require

  已开发出一种新的制备与潜在细胞毒性剂有关的异恶唑基乙烯基酮的方法。在第一步中，糠基酮与羟胺盐酸盐的反应得到相应的肟。此外，肟的氧化开环-闭环反应会生成具有α，β-不饱和羰基的异恶唑。开发的程序不含金属，不需要昂贵的原材料。
• Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini

  DOI：10.1021/jo00058a011

  日期：1993.3

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.
• Gold catalysis: benzanellation versus alkylidenecyclopentenone synthesis
  作者：A. Stephen K. Hashmi、Michael Wölfle

  DOI：10.1016/j.tet.2009.08.074

  日期：2009.10

  A series of different furan-yn-ols were prepared by a three-step sequence. Their reaction with Gagosz's catalyst Ph3PAuNTf2 depends strongly on the substitution pattern of the Substrate and the quality of the leaving group. Benzofurans, alkylidenecyclopentenones or Meyer-Schuster type products can be obtained. Improving the leaving group quality leads to the preferred formation of benzofurans. (C) 2009 Elsevier Ltd. All rights reserved.