2-(3-acetoxy-1-propynyl)thiophene | 157223-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(3-acetoxy-1-propynyl)thiophene
• 英文别名: 2-(3-acetoxyprop-1-ynyl)thiophene；3-acetoxy-1-(2-thienyl)-1-propyne；3-(2-thienyl)-2-propynyl acetate；3-Thiophen-2-ylprop-2-ynyl acetate
• CAS: 157223-45-5
• 化学式: C₉H₈O₂S
• 分子量: 180.227
• InChiKey: WTAFLHULRONPNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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-(3-acetoxy-1-propynyl)thiophene 在 三氟化硼乙醚 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.0h， 生成 (3-oxo-2-(thiophen-2-yl)cycloprop-1-enyl)methyl acetate
  参考文献：
  名称：

  Lewis碱催化的环丙烯酮反应：单取代或多取代的烯丙酸酯的新颖合成。

  摘要：

  环丙烯酮与亲核试剂（H2O或甲醇）的反应可以通过含氮的路易斯碱或含磷的路易斯碱催化，从而以中等至极好的收率提供相应的单取代或多取代的烯丙酸酯。

  DOI：

  10.1039/c3cc46470a
• 作为产物：
  描述：

  thiophen-2-yl-propynoic acid ethyl ester 在 lithium diisobutylaluminium hydride 作用下， 生成 2-(3-acetoxy-1-propynyl)thiophene
  参考文献：
  名称：

  Photocoupling between Haloheterocyclic Derivatives and Arylalkenes and Arylalkynes: Instruments to Predict Reactivity

  摘要：

  Parameters useful to predict reactivity and regiochemical control of photocoupling reactions between haloheterocyclic derivatives and arylalkenes or arylalkynes have been studied. Electrochemical properties of arylalkenes and arylalkynes are shown to be useful to predict the reactivity of the substrates. However, oxidation potentials fail as reactivity indices if very fast photochemical processes are in competition with the observed complex formation between substrates and halogen atoms. The regiochemical behavior of the reaction can be estimated on the basis of dipoles of the reagents. In this case the assumptions that a reagent approaches the other on parallel planes and that the prevalent interaction is between the SOMO of the radical and the LUMO of the other reagent have been accepted.

  DOI：

  10.1021/jo00131a008

文献信息

• Straightforward Synthesis of Nonconjugated Cyclohex-3-enone and Conjugated 4-Methylenecyclohex-2-enone Derivatives
  作者：Gerhard Hilt、Julian Kuttner、Svenja Warratz

  DOI：10.1055/s-0031-1289752

  日期：2012.5

  The synthesis of nonconjugated cyclohex-3-enones via the regiodivergent cobalt-catalysed Diels-Alder reactions of 2-(trimethylsilyloxy)buta-1,3-diene with alkynes and hydrolysis of the dihydroaromatic intermediates is described. The application of bidentate phosphine ligands versus pyridine-imine ligands led to the regioselective formation of one out of the two possible regioisomeric products when

  描述了通过2-（三甲基甲硅烷基氧基）buta-1,3-二烯与炔烃的区域发散性钴催化的Diels-Alder反应和二氢芳族中间体的水解来合成非共轭环己-3-烯酮。当应用末端或不对称取代的炔烃时，二齿膦配体相对于吡啶-亚胺配体的应用导致两种可能的区域异构产物之一的区域选择性形成。根据温和的反应条件，大多数以高收率分离出环己-3-烯酮产物，而没有碳-碳双键异构化成共轭。在甲硅烷基烯醇醚脱保护后，使用乙酰氧基甲基取代的炔烃产生共轭的4-亚甲基环己-2-烯酮。 炔烃-催化-钴-狄尔斯-阿尔德反应-二烯-非共轭
• Indium Chloride Catalyzed Alkylative Rearrangement of Propargylic Acetates Using Alkyl Chlorides, Alcohols, and Acetates: Facile Synthesis of α-Alkyl-α,β-Unsaturated Carbonyl Compounds
  作者：Yoshiharu Onishi、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol500046e

  日期：2014.2.21

  Indium chloride catalyzed alkylative rearrangement of propargylic acetates into α-alkyl-α,β-unsaturated carbonyl compounds has been achieved. Propargylic acetates functioned as α-acylvinyl anion equivalents to react with carbocations generated from alkyl chlorides. Other alkyl electrophiles such as alcohols and acetates were also applicable.

  已经实现了氯化铟催化的炔丙基乙酸酯的烷基化重排成α-烷基-α，β-不饱和羰基化合物。炔丙基乙酸酯起α-酰基乙烯基阴离子当量的作用，与由烷基氯化物产生的碳正离子反应。其他烷基亲电子试剂，例如醇和乙酸酯也是适用的。
• Direct Synthesis of α-Iodoenones by IPy₂BF₄-Promoted Rearrangement of Propargylic Esters
  作者：Tatiana Suárez-Rodríguez、Ángel L. Suárez-Sobrino、Alfredo Ballesteros

  DOI：10.1021/acs.joc.8b01746

  日期：2018.10.19

  A direct access to α-iodoeones from iodonium ion and propargylic tosylates or acetates is described. Bis(pyridine) iodonium tetrafluoroborate (IPy2BF4, Barluenga’s reagent) promotes the rearrangement of these propargylic alcohol derivatives in mild conditions. The transformation gives β-unsubstituted, β-monosubstituted, and β,β-disubstituted α-iodoenones in high yields. β-Substituted α-iodoenones are

  描述了从碘鎓离子和炔丙基甲苯磺酸盐或乙酸盐直接获得α-碘酮的方法。双（吡啶）四氟硼酸碘鎓盐（IPy 2 BF 4，Barluenga的试剂）在温和条件下促进这些炔丙醇衍生物的重排。该转化以高产率产生β-未取代的，β-单取代的和β，β-二取代的α-碘烯。以优异的（Z）选择性获得β-取代的α-碘烯。
• D'Agostini, Agnese; D'Auria, Maurizio, Journal of the Chemical Society. Perkin transactions I, 1994, # 9, p. 1245 - 1250
  作者：D'Agostini, Agnese、D'Auria, Maurizio

  DOI：——

  日期：——
• DAgostini Agnesse, DAuria Maurizio, J. Chem. Soc. Perkin Trans. 1, (1994) N 9, S 1245-1249
  作者：DAgostini Agnesse, DAuria Maurizio

  DOI：——

  日期：——