1-(2-methyl-5-phenyl-3-furanyl)ethanone | 43020-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methyl-5-phenyl-3-furanyl)ethanone
• 英文别名: 1-(2-methyl-5-phenylfuran-3-yl)ethanone；3-acetyl-2-methyl-5-phenylfuran；1-(2-methyl-5-phenylfuran-3-yl)ethan-1-one；4-Acetyl-2-phenyl-5-methyl-furan；2-Methyl-3-acetyl-5-phenylfuran
• CAS: 43020-10-6
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: VKHYKLRXCGXSOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  1-(2-methyl-5-phenyl-3-furanyl)ethanone 在 氢氧化钾 、 乙醇 、 sodium ethanolate 、 乙酸酐 作用下， 生成 2-甲基-5-苯基呋喃-3-羧酸
  参考文献：
  名称：

  Sprio; Madonia, Gazzetta Chimica Italiana, 1957, vol. 87, p. 454,465

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮肟 在 copper(l) iodide 、 manganese(III) triacetate dihydrate 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 1-(2-methyl-5-phenyl-3-furanyl)ethanone
  参考文献：
  名称：

  Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides

  摘要：

  An efficient manganese(III)-mediated oxidative coupling reaction between a-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

  DOI：

  10.1021/ol503009f

文献信息

• Synthesis of the Derivatives of 4-(5-Aryl-3-methylfuran-3-yl)-1,2,3-thiadiazole and Functionalization of 5-Aryl-2- methylfuran via Reactions of Thiadiazole Ring
  作者：Yu. O. Remizov、L. M. Pevzner、M. L. Petrov

  DOI：10.1134/s1070363218070095

  日期：2018.7

  2-methyl-3-acetylfuran via the Gomberg–Bachmann reaction 5-(4-ethoxycarbonylphenyl)-, 5-(2-nitrophenyl), and 5-(4-nitrophenyl)-2-methyl-3-acetylfurans were synthesized. Carboethoxyhydrazones of 2-methyl-5-phenyl-3-acetylfuran and its phenyl-substituted analogs when treated with thionyl chloride form 4-(5-aryl-2-methylfuran-3-yl)-1,2,3-thiadiazoles by the Hurd–Mori reaction. Thermal stability of obtained compounds

  通过Gomberg-Bachmann反应将2-甲基-3-乙酰基呋喃芳基化，得到5-（4-乙氧基羰基苯基）-，5-（2-硝基苯基）和5-（4-硝基苯基）-2-甲基-3-乙酰基呋喃合成的。当用亚硫酰氯处理时，2-甲基-5-苯基-3-乙酰基呋喃的碳乙氧基hydr及其苯基取代的类似物通过以下方式形成4-（5-芳基-2-甲基呋喃-3-基）-1,2,3-噻二唑。赫德-莫里反应。所获得的化合物的热稳定性随着苯环中取代基的电子受体作用的增加而增加。叔丁基钾作用下合成的化合物中噻唑环的开环在烷基碘的存在下，在THF中的丁酸生成相应的烷基硫代乙炔基呋喃。在过量吗啉存在下与碳酸钾在DMF中进行反应，可以制备（2-甲基-5-芳基呋喃-3-基）硫代乙酰吗啉。
• One-Pot Synthesis of Furans Using Base- and Acid-Supported Reagents ‘Na2CO3/Al2O3-PPA/SiO2'
  作者：Tadashi Aoyama、Takashi Nagaoka、Toshio Takido、Mitsuo Kodomari

  DOI：10.1055/s-0030-1258402

  日期：2011.2

  convenient method for the one-pot synthesis of furans from β-keto esters and α-halo ketones was developed using an acid- and base-supported reagent system ‘Na2CO3/Al2O3-PPA/SiO2’. The condensation reaction of triketones, which are formed from the reaction of β-keto esters with α-halo ketones in the presence of Na2CO3/Al2O3, was promoted by PPA/SiO2 to give the corresponding furans in good yields. This method

  开发了一种方便的方法，可使用酸和碱支持的试剂系统'Na 2 CO 3 / Al 2 O 3 -PPA / SiO 2 '从β-酮酯和α-卤代酮一锅合成呋喃。PPA / SiO 2促进了β-酮酸酯与α-卤代酮在Na 2 CO 3 / Al 2 O 3存在下的反应而形成的三酮缩合反应，得到了相应的呋喃。产量。与分步法相比，该方法简单易行，收率好。 呋喃-一锅合成-支持的试剂
• Regioselective Synthesis of Highly Functionalized Furans Through the Ru^II-Catalyzed [3+2] Cycloaddition of Diazodicarbonyl Compounds
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1002/ejoc.201402067

  日期：2014.6

  A novel method for the RuII-catalyzed regioselective synthesis of highly functionalized furans from readily available cyclic and acyclic diazodicarbonyl compounds and terminal alkynes is described. The devised protocol offers a straightforward means to the construction of a variety of diverse furan derivatives through powerful cascade processes, including the formation of ruthenium carbenoid, cyclopropenation

  描述了一种从容易获得的环状和非环状重氮二羰基化合物和末端炔烃中 RuII 催化区域选择性合成高度官能化呋喃的新方法。设计的协议为通过强大的级联过程构建各种不同的呋喃衍生物提供了一种直接的方法，包括钌卡宾的形成、环丙烯化、开环复分解和环化。
• SUBSTITUTED FURANS AND THEIR USE
  申请人：Lampe Thomas

  公开号：US20110054017A1

  公开（公告）日：2011-03-03

  The present application relates to novel substituted furan derivatives, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.

  本申请涉及新颖的取代呋喃衍生物，涉及它们的制备方法，涉及它们用于治疗和/或预防疾病以及用于制备治疗和/或预防疾病药物的用途，特别是用于治疗和/或预防心血管疾病。
• Cobalt(II)-Catalyzed Electrophilic Alkynylation of 1,3-Dicarbonyl Compounds To Form Polysubstituted Furans<i>via</i>π-π Activation
  作者：Irwan Iskandar Roslan、Jiulong Sun、Gaik-Khuan Chuah、Stephan Jaenicke

  DOI：10.1002/adsc.201400857

  日期：2015.3.9

  Polysubstituted furans were obtained with excellent yields via the electrophilic alkynylation of 1,3‐dicarbonyl compoundsws with phenyl‐ or ester‐substituted brominated alkynes. The reaction is catalyzed by the inexpensive and readily available catalyst, cobalt(II) chloride, and has a wide substrate scope. The C(sp)C(sp3) coupling occurs under mild conditions with short reaction times and does not

  多取代呋喃是通过1,3-二羰基化合物ws与苯基或酯取代的溴代炔烃的亲电炔基化而获得的，具有优异的收率。该反应由廉价且容易获得的催化剂氯化钴（II）催化，并且具有广泛的底物范围。C（sp）C（sp 3）偶联在温和的条件下发生，反应时间短，不需要惰性气氛或配体。建议反应通过钴（II）与去质子化的1,3-二羰基化合物的螯合配合物进行。