1-(2-甲基-5-(4-甲氧基苯基)-3-呋喃基)乙酮 | 34695-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(2-甲基-5-(4-甲氧基苯基)-3-呋喃基)乙酮
• 英文名称: 3-acetyl-5-(4-methoxyphenyl)-2-methylfuran
• 英文别名: 1-(5-(4-methoxyphenyl)-2-methylfuran-3-yl)ethanone；1-[5-(4-Methoxyphenyl)-2-methyl-3-furyl]ethanone；1-[5-(4-methoxyphenyl)-2-methylfuran-3-yl]ethanone
• CAS: 34695-13-1
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: ZFVJOSWPOVFKMV-UHFFFAOYSA-N

物化性质

• 熔点：
  88-92 °C
• 沸点：
  355.9±42.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-甲基-5-(4-甲氧基苯基)-3-呋喃基)乙酮 在 氧气 、 rose bengal 、 水 作用下， 以 乙腈 为溶剂， 反应 1.08h， 以67%的产率得到3-乙酰基-1-(4-甲氧基苯基)戊-2-烯-1,4-二酮
  参考文献：
  名称：

  Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions

  摘要：

  The photooxygenation of 3-acetyl-5-aryl-2-methylfurans la-e selectively produced 2,2-diacetyl-3-aroyloxiranes 2a-e, 3-acetyl-1-aryl-2-pentene-1,4-diones 3a-e, and 3-acetyl-1-aryl-2-hydroxy-2-pentene-1,4-diones 4a-d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a-e were mainly obtained in 56-77% yields by allowing the reaction mixture to stand at ambient temperature after the irradiation, while the treatment of the reaction mixture with water mainly gave the 1,4-diones 3a-e (62-69%). Heating the reaction mixture at 80 degreesC after the irradiation decreased the total yield of the products, however, the enols 4a-d were newly formed in 8-12% yields. Direct UV irradiation of the endoperoxide intermediate A led to the homolytic fission of the peroxide linkage to produce the same enols 4a-e (16-39%). The self-sensitized photooxygenation of 1a-d using a UV light also gave 4a-d in a similar yield. The reaction pathway is discussed based on these results. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00559-2
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 反应 3.0h， 生成 1-(2-甲基-5-(4-甲氧基苯基)-3-呋喃基)乙酮
  参考文献：
  名称：

  3-亚甲基呋喃-2（3 H）-一的快速真空热解法形成烯基酮，3-乙炔香豆素和芳基呋喃，呋喃基呋喃和呋喃基噻吩

  摘要：

  3- methylidenefuran-2（3闪热解真空（FVT）ħ） -酮3倍的原因的CO cheletropic挤出与地层丙二烯基酮4。Ò氯代和ö -bromophenylmethylidenefuranones也得到在闪速热解真空丙二烯基酮，但除此之外，3- ethynylcoumarins 6经由形成é / Ž的methylidenefuranones，环化，卤素原子迁移，和HCl（HBR）消除异构化。酰基丙二烯部分上存在强吸电子基团（硝基芳基或乙酰基）会引起重排，从而生成2-芳基呋喃10和13以及通过烯基酮的环化作用的2-呋喃呋喃和2-呋喃噻吩16。在M06-2X / 6-311 + G（d，p）的理论水平上的计算为反应机理提供了支持。

  DOI：

  10.1021/jo402139a

文献信息

• Copper-Catalyzed Coupling Cyclization of <i>gem</i>-Difluoroalkenes with Activated Methylene Carbonyl Compounds: Facile Domino Access to Polysubstituted Furans
  作者：Xuxue Zhang、Wenpeng Dai、Wei Wu、Song Cao

  DOI：10.1021/acs.orglett.5b01123

  日期：2015.6.5

  A novel and efficient CuI-catalyzed synthesis of 2,3,5-trisubstituted furans was developed via coupling cyclization of gem-difluoroalkenes with active methylene carbonyl compounds such as 1,3-dicarbonyl compounds, acetoacetonitrile, and phenylsulfonylacetone with the assistance of a base. Commercial availability of substrates or reagents, good to high isolated yields, and excellent functional group

  通过宝石-二氟烯烃与活性亚甲基羰基化合物（例如1,3-二羰基化合物，乙酰乙腈和苯磺酰丙酮）的偶联环化，开发了新颖，高效的CuI催化的2,3,5-三取代呋喃合成方法。底物或试剂的商业可得性，良好或较高的分离产率以及出色的官能团相容性，使这种转化成为合成各种呋喃的有力工具。提出了一种可能的机制，涉及到烯丙基酮。
• Auto-Tandem Catalysis-Induced Synthesis of Trisubstituted Furans through Domino Acid-Acid-Catalyzed Reaction of Aliphatic Aldehydes and 1,3-Dicarbonyl Compounds by using<i>N</i>-Bromosuccinimide as Oxidant
  作者：Wenbo Huang、Changhui Liu、Yanlong Gu

  DOI：10.1002/adsc.201700074

  日期：2017.6.6

  A simple aluminium(III) chloride‐catalyzed synthesis of tri‐substituted furans from aliphatic aldehydes and 1,3‐dicarbonyl compounds was developed by using N‐bromosuccinimide (NBS) as an oxidant. This method was effective for the synthesis of various furan derivatives. Some of the products were not accessible with the previously reported methods. Mechanically, this reaction involved an auto‐tandem

  使用N-溴代琥珀酰亚胺（NBS）作为氧化剂，开发了一种简单的氯化铝（III）催化的脂肪族醛和1,3-二羰基化合物合成三取代呋喃的方法。该方法对于合成各种呋喃衍生物是有效的。使用先前报告的方法无法访问某些产品。从机械上讲，该反应涉及一种基于新报道的酸-酸催化串联反应的自动串联催化，以确保呋喃得以成功合成。
• 由偕二氟烯烃制备多取代呋喃衍生物的方法
  申请人：华东理工大学

  公开号：CN104910105B

  公开（公告）日：2017-04-05

  本发明涉及一种制备多取代呋喃衍生物的方法，所述方法的主要步骤是：在有铜盐及元素周期表中ⅠA中元素的含氧酸盐存在条件下，由偕二氟烯烃与含活泼亚甲基化合物在非质子有机溶剂中，于90C～120C反应，得到目标物(2,3,5‑三取代呋喃衍生物)。本发明具有低成本(避免使用贵金属为催化剂)、底物易得及适应性广和产物具有多样性等优点。
• Direct synthesis of furans by 3 + 2 cycloadditions between rhodium(II) acetate stabilized carbenoids and acetylenes
  作者：Huv M.L. Davies、Karen R. Romines

  DOI：10.1016/s0040-4020(01)85968-8

  日期：1988.1

  Whan appropriate substituents are used, rhodium(II) acatate catalyzed decomposition of diazocarbonyls in the presence of acetylenes results in the formation of furans, derived from dipolar intermediates.

  如果使用合适的取代基，则在乙炔的存在下，过氧化铑铑（II）催化重氮羰基的分解会导致衍生自偶极中间体的呋喃的形成。
• Electrocatalytic [3 + 2] Annulation for the Synthesis of Polysubstituted Furans
  作者：Ming Chen、Jian Wang、Yuanmeng Kan、Xiaoni Jia、Binbin Huang、Ting Li、Xinxin Zhao

  DOI：10.1021/acs.orglett.3c01582

  日期：2023.6.23

  atom-economic, practical strategy for the synthesis of tri/tetra-substituted furans through electrochemical [3 + 2] annulation between alkynes and β-keto compounds with ferrocene (Fc) as the catalyst. This protocol features the use of a graphite felt (GF) anode and a stainless steel (SST) cathode, mild conditions, and excellent tolerance with various alkynes and β-keto compounds. Additionally, the application

  在本报告中，我们描述了一种原子经济、实用的策略，以二茂铁 (Fc) 作为催化剂，通过炔烃和 β-酮化合物之间的电化学 [3 + 2] 成环来合成三/四取代呋喃。该协议的特点是使用石墨毡 (GF) 阳极和不锈钢 (SST) 阴极、温和的条件以及对各种炔烃和 β-酮化合物的优异耐受性。此外，复杂结构的后期功能化和克级实验凸显了该方法的应用。