1-bromo-2-(2-thenoyl)acetylene | 54289-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-2-(2-thenoyl)acetylene
• 英文别名: 1-bromo-2-thenoylacetylene；3-bromo-1-(thiophen-2-yl)prop-2-yn-1-one；2-Propyn-1-one, 3-bromo-1-(2-thienyl)-；3-bromo-1-thiophen-2-ylprop-2-yn-1-one
• CAS: 54289-75-7
• 化学式: C₇H₃BrOS
• 分子量: 215.07
• InChiKey: KAOKHUFZTGVUOM-UHFFFAOYSA-N

物化性质

• 熔点：
  83 °C
• 沸点：
  283.9±32.0 °C(Predicted)
• 密度：
  1.742±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(2-thenoyl)acetylene 在 sodium selenide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以77%的产率得到(E)-2,4-bis(2-thienoylmethylene)-1,3-diselenetane
  参考文献：
  名称：

  Reactions of sodium selenide with ethynyl and bromoethynyl ketones: Stereo- and regioselective synthesis of functionalized divinyl selenides and 1,3-diselenetanes

  摘要：

  A method for the preparation of 2,4-dimethylene-1,3-diselenetanes based on the novel reaction of sodium selenide with bromoethynyl ketones has been developed. New functionalized divinyl selenides have been obtained by regio- and stereoselective addition of sodium selenide to ethynyl ketones. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.07.023
• 作为产物：
  描述：

  3-bromo-1-(thiophen-2-yl)prop-2-yn-1-ol 在 manganese(IV) oxide 作用下， 以75%的产率得到1-bromo-2-(2-thenoyl)acetylene
  参考文献：
  名称：

  Synthesis of substituted 2-amino-1,3-thiazine-6-thiones

  摘要：

  The reaction of thiourea with 1-acyl-2-bromoacetylenes in AcOH in the presence of BF3. Et2O affords 2-amino-4-phenyl(2-thienyl)-1,3-thiazine-6-thiones in high yields.

  DOI：

  10.1007/bf02494937

文献信息

• Ruthenium-Catalyzed Cycloadditions of 1-Haloalkynes with Nitrile Oxides and Organic Azides: Synthesis of 4-Haloisoxazoles and 5-Halotriazoles
  作者：James S. Oakdale、Rakesh K. Sit、Valery V. Fokin

  DOI：10.1002/chem.201402559

  日期：2014.8.25

  (Cyclopentadienyl)(cyclooctadiene) ruthenium(II) chloride [CpRuCl(cod)] catalyzes the reaction between nitrile oxides and electronically deficient 1‐choro‐, 1‐bromo‐, and 1‐iodoalkynes leading to 4‐haloisoxazoles. Organic azides are also suitable 1,3‐dipoles, resulting in 5‐halo‐1,2,3‐triazoles. These air‐tolerant reactions can be performed at room temperature with 1.25 equivalents of the respective

  （环戊二烯基）（环辛二烯）氯化钌（II）[CpRuCl(cod)] 催化腈氧化物与电子缺陷的 1-氯-、1-溴-和 1-碘炔之间的反应，生成 4-卤代异恶唑。有机叠氮化物也是合适的 1,3-偶极子，产生 5-卤代-1,2,3-三唑。这些耐空气反应可以在室温下进行，相对于炔烃组分，相应的 1,3-偶极子为 1.25 当量。反应性 1-卤代炔烃包括丙炔酰胺、酯、酮和膦酸酯。卤化唑类产物的后官能化可以通过钯催化的交叉偶联反应和活性酰胺基团的操作来实现。用 [Cp*RuCl(cod)]（Cp*=五甲基环戊二烯基）观察到的催化缺乏归因于 Cp* 的空间需求（η 5 ‐C 5 Me 5 ) 配体与母体 Cp ( η 5 ‐C 5 H 5 ) 相比。[( η 5 ‐C 5 Me 4 CF 3 )RuCl(cod)]的低反应性支持了这一假设，它作为 Cp* 的等排模拟物和 Cp 的等电子类似物。
• Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides
  作者：Lucile Andna、Laurence Miesch

  DOI：10.1039/c9ob00947g

  日期：——

  An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.

  描述了活化的炔磺酰胺和烯磺酰胺的操作简单的合成。可以通过在室温下短时间内使磺酰胺类化合物与活化的溴炔烃和Triton B反应来获得丙磺酰胺。同样，末端炔烃与磺酰胺反应以提供烯磺酰胺。Z / E磺酰胺可以仅转化为E磺酰胺。
• From 4,5,6,7-tetrahydroindoles to 3- or 5-(4,5,6,7-tetrahydroindol-2-yl)isoxazoles in two steps: a regioselective switch between 3- and 5-isomers
  作者：Lyubov N. Sobenina、Denis N. Tomilin、Maxim D. Gotsko、Igor A. Ushakov、Albina I. Mikhaleva、Boris A. Trofimov

  DOI：10.1016/j.tet.2014.05.099

  日期：2014.8

  (4,5,6,7-Tetrahydroindo1-2-yl]alkynes, synthesized by cross-coupling of 4,5,6,7-tetrahydroindoles with aroyl(hetaroyl)bromoallcynes or ethyl bromopropynoate in the presence of K2CO3, regioselectively cyclize with hydroxylamine to either 3- or 5-(4,5,6,7-tetrahydroindol-2-yl)isoxazoles depending on the acidity of the reaction mixture: in the presence of acetic acid 3-isomers are formed (ca. 100% selectivity), while under neutral conditions the reaction is switched to 5-isomers (94-97% selectivity). (C) 2014 Published by Elsevier Ltd.

  由4,5,6,7-四氢吲哚与芳香酰基（杂环芳酰基）溴代炔烃或乙基溴代丙二烯酸酯在K₂CO₃存在下进行交叉偶联反应，可合成出带有4,5,6,7-四氢吲哚-2-基的炔烃。这些炔烃能选择性地与羟胺环化，生成3-或5-(4,5,6,7-四氢吲哚-2-基)异噁唑，这取决于反应混合物的酸性：在醋酸存在下，主要生成3-异构体（约100%选择性），而在中性条件下，则转向生成5-异构体（94-97%选择性）。 ©2014 Elsevier Ltd.出版。
• Functionalized Bipyrroles and Pyrrolyl-Aminopyrones from Acylethynylpyrroles and Diethyl Aminomalonate
  作者：Boris A. Trofimov、Maxim D. Gotsko、Ivan V. Saliy、Lyubov N. Sobenina、Igor A. Ushakov、Victoriya V. Kireeva

  DOI：10.1055/a-1681-4164

  日期：2022.2

  72% yield) by the cyclocondensation of easily available 2-(acylethynyl)pyrroles with diethyl aminomalonate hydrochloride has been developed. The reaction proceeds under reflux in MeCN (6 h) in the presence of Cs2CO3. Under the same conditions, 2-(acylethynyl)pyrroles with bulky (benzyl and octyl) substituents at nitrogen atom react with diethyl aminomalonate to afford 1H,2′H-2,3′-bipyrroles and pyrrolyl-aminopyrones

  已开发出一种通过容易获得的 2-（酰基乙炔基）吡咯与氨基丙二酸二乙酯盐酸盐的环缩合反应来合成 1H,1'H-2,3'-联吡咯（产率高达 72%）的有效方法。在 Cs2CO3 存在下，反应在 MeCN 中回流进行（6 小时）。在相同条件下，氮原子上带有大量（苄基和辛基）取代基的 2-（酰基乙炔基）吡咯与氨基丙二酸二乙酯反应生成 1H,2'H-2,3'-联吡咯和吡咯基-氨基吡咯酮。
• Synthesis of 2,2-di(pyrazol-1-yl)enones via the 2:1 coupling of pyrazoles and acylbromoacetylenes in solid alumina
  作者：Maxim D. Gotsko、Lyubov' N. Sobenina、Alexander V. Vashchenko、Boris A. Trofimov

  DOI：10.1016/j.tetlet.2018.10.033

  日期：2018.11

  intermediates, (Z)-2-bromo-2-(pyrazol-1-yl)enones. This unexpected 2:1 coupling is in contrast to similar reactions of pyrroles, furans and thiophenes, which give the corresponding acylethynyl derivatives. This reaction opens a one-pot route to inaccessible gem-dipyrazolylenones, which have potential applications as bidentate chelating ligands and building blocks for drug design.

  吡唑在室温下与固体Al 2 O 3中的酰基溴乙炔反应，以22-69％的产率提供2,2-二（吡唑-1-基）烯酮。反应通过可分离的中间体（Z） -2-溴-2-（吡唑-1-基）烯酮进行。这种出乎意料的2：1偶联与吡咯，呋喃和噻吩的类似反应形成了相应的酰基乙炔基衍生物。该反应为难于获得的宝石-二吡唑基亚酮打开了一条锅路，这些潜在的应用有可能用作双齿螯合配体和药物设计的基础。