1-(2-methyl-5-(thiophen-2-yl)furan-3-yl)ethanone | 134638-56-5

• 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-(thiophen-2-yl)furan-3-yl)ethanone
• 英文别名: 1-(2-Methyl-5-thiophen-2-ylfuran-3-yl)ethanone
• CAS: 134638-56-5
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: WFCRVZFYUFJDDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  315.5±42.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(1-(thiophen-2-yl)vinyl)acetamide 在 manganese(III) triacetate dihydrate 、 对甲苯磺酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 1-(2-methyl-5-(thiophen-2-yl)furan-3-yl)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

• Formation of Allenyl Ketones, 3-Ethynylcoumarins, and Arylfurans, Furylfurans, and Furylthiophenes by Flash Vacuum Thermolysis of 3-Methylidenefuran-2(3<i>H</i>)-ones
  作者：Rainer Koch、Hans Michael Berstermann、Curt Wentrup

  DOI：10.1021/jo402139a

  日期：2014.1.3

  Flash vacuum thermolysis (FVT) of 3-methylidenefuran-2(3H)-ones 3 causes cheletropic extrusion of CO with formation of allenyl ketones 4. o-Chloro- and o-bromophenylmethylidenefuranones also afford allenyl ketones upon flash vacuum thermolysis, but in addition, 3-ethynylcoumarins 6 are formed via E/Z isomerization of the methylidenefuranones, cyclization, halogen atom migration, and HCl (HBr) elimination

  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。
• 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。
• Novel photoactive compounds, processes for their production and intermediates therefor
  申请人：MTM RESEARCH CHEMICALS LIMITED

  公开号：EP0334477A2

  公开（公告）日：1989-09-27

  Photoactive compounds having the general formulae below are provided in which A represents oxygen or specified imido groups; P' represents a 3-furyl, a 3-thienyl, a 3-pyrryl, a 3-benzofuryl or a 3-benzothienyl group, said 3-furyl, 3-thienyl and 3-pyrryl groups which is unsubstituted or substituted in the 2-position and/or the 5-position, with specified substituents; p2 represents alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aralkyl having 7 to 9 carbon atoms, aryl having 6 to 14 carbon atoms which may be unsubstituted or substituted with one or more halogen atoms, or alkaryl having 7 to 22 carbon atoms; and F>C* and E>C* represent a substituted or unsubstituted bridged polycyclic hydrocarbon residue containing from 7 to 20 carbon atoms in a polycyclic system, said residue having a plane of asymmetry which is parallel to the plane which includes the single bonds extending from carbon atom C* and the anhydride or imide ring, any substituents on the bridged polycyclic hydrocarbyl residue being selected from alkyl groups having 1 to 4 carbon atoms, halogen atoms and hydroxy groups.

  提供了具有以下通式的光活性化合物 其中 A 代表氧或特定亚氨基； P'代表3-呋喃基、3-噻吩基、3-吡喃基、3-苯并呋喃基或3-苯并噻吩基，所述3-呋喃基、3-噻吩基和3-吡喃基未被取代或在2位和/或5位被指定的取代基取代； p2 代表具有 1 至 20 个碳原子的烷基、具有 3 至 12 个碳原子的环烷基、具有 7 至 9 个碳原子的芳烷基、具有 6 至 14 个碳原子且未被取代或被一个或多个卤素原子取代的芳基或具有 7 至 22 个碳原子的烷芳基；以及 F>C* 和 E>C* 代表在多环体系中含有 7 至 20 个碳原子的取代或未取代的桥接多环烃残基，所述残基的不对称平面平行于包括从碳原子 C* 和酸酐或亚胺环延伸的单键的平面，桥接多环烃残基上的任何取代基均选自具有 1 至 4 个碳原子的烷基、卤素原子和羟基。