2-((4-methoxyphenyl)thiocarbonyl)furan | 136912-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-methoxyphenyl)thiocarbonyl)furan
• 英文别名: Furan-2-yl-(4-methoxyphenyl)methanethione
• CAS: 136912-36-2
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: HHXMGQGTQFHBED-UHFFFAOYSA-N

物化性质

• 沸点：
  326.3±48.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((4-methoxyphenyl)thiocarbonyl)furan 、 Prop-2-ynyl 2-bromoprop-2-enoate 以 苯 为溶剂， 反应 0.5h， 以42%的产率得到7-(4-Methoxy-phenyl)-5H-thiopyrano[3,4-b]furan-4-carboxylic acid prop-2-ynyl ester
  参考文献：
  名称：

  A Simple and Efficient Synthesis of Heterocycle-Fused 2H-Thiopyrans, Furo-, Benzofuro-, Thieno-, Benzothieno-, Pyrrolo- and Indolo-2H- thiopyrans, from Heteroaromatic Thioketones and α-Chloroacrylonitrile or α-Bromoacrylic Esters via a Hetero Diels-Alder Reaction-Dehydrohalogenation Process

  摘要：

  本研究介绍了一种高效便捷的方法，以杂芳族硫酮和δ±-氯丙烯腈或δ±-溴丙烯酸酯为起点，通过杂环 Diels-Alder 反应-氢卤化过程合成具有正二甲苯结构的杂环融合 2H-硫代吡喃。

  DOI：

  10.1055/s-1994-25558
• 作为产物：
  描述：

  2-呋喃基(4-甲氧基苯基)甲酮 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以72%的产率得到2-((4-methoxyphenyl)thiocarbonyl)furan
  参考文献：
  名称：

  Silicon-assisted synthesis of thiocarbonyl derivatives and reactivity of dienophilic thioaldehydes

  摘要：

  Treatment of bis(trimethylsilyl) sulfide with CoCl2.6H2O in the presence of aldehydes affords the corresponding thiocarbonyl analogues which can be trapped to avoid polymerization. The sulfurization reaction also takes place in the presence of TfOSiMe3, in which case, besides thioaldehydes, thioketones may be obtained in satisfactory yields. When thioaldehydes are generated with the CoCl2.6H2O method the Diels-Alder reaction with cyclohexadiene occurs with very high selectivity in favor of the endo isomer, whereas when the TfOSiMe3-based method is employed, the stereochemistry of the cycloadduct can be conveniently selected toward endo or exo by varying the molar ratio of the sulfurating agent.

  DOI：

  10.1021/jo00026a025

文献信息

• Silicon-assisted synthesis of thiocarbonyl derivatives and reactivity of dienophilic thioaldehydes
  作者：Antonella Capperucci、Alessandro Degl'Innocenti、Alfredo Ricci、Alessandro Mordini、Gianna Reginato

  DOI：10.1021/jo00026a025

  日期：1991.12

  Treatment of bis(trimethylsilyl) sulfide with CoCl2.6H2O in the presence of aldehydes affords the corresponding thiocarbonyl analogues which can be trapped to avoid polymerization. The sulfurization reaction also takes place in the presence of TfOSiMe3, in which case, besides thioaldehydes, thioketones may be obtained in satisfactory yields. When thioaldehydes are generated with the CoCl2.6H2O method the Diels-Alder reaction with cyclohexadiene occurs with very high selectivity in favor of the endo isomer, whereas when the TfOSiMe3-based method is employed, the stereochemistry of the cycloadduct can be conveniently selected toward endo or exo by varying the molar ratio of the sulfurating agent.
• A Simple and Efficient Synthesis of Heterocycle-Fused 2<i>H</i>-Thiopyrans, Furo-, Benzofuro-, Thieno-, Benzothieno-, Pyrrolo- and Indolo-2<i>H</i>- thiopyrans, from Heteroaromatic Thioketones and α-Chloroacrylonitrile or α-Bromoacrylic Esters via a Hetero Diels-Alder Reaction-Dehydrohalogenation Process
  作者：Takao Saito、Takuya Shizuta、Hideki Kikuchi、Junko Nakagawa、Kenji Hirotsu、Haruo Ohmura、Shinichi Motoki

  DOI：10.1055/s-1994-25558

  日期：——

  An efficient and convenient procedure is described for the synthesis of heterocycle-fused 2H-thiopyrans having ortho-dimethylene structures via a hetero Diels-Alder reaction-dehydrohalogenation process starting from heteroaromatic thioketones and α-chloro-acrylonitrile or α-bromoacrylates.

  本研究介绍了一种高效便捷的方法，以杂芳族硫酮和δ±-氯丙烯腈或δ±-溴丙烯酸酯为起点，通过杂环 Diels-Alder 反应-氢卤化过程合成具有正二甲苯结构的杂环融合 2H-硫代吡喃。