3-(4-methoxyphenyl)-1-(thiophen-2-yl)prop-2-yn-1-one | 29784-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-1-(thiophen-2-yl)prop-2-yn-1-one
• 英文别名: 3-(4-methoxyphenyl)-1-thiophen-2-ylprop-2-yn-1-one
• CAS: 29784-22-3
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: ALOBMIUZTDCZNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(thiophen-2-yl)prop-2-yn-1-one 、 2-氨基苯甲腈 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以88%的产率得到(4–amino–2–(4–methoxyphenyl)quinolin–3–yl)(thiophen–2–yl)methanone
  参考文献：
  名称：

  Base‐Promoted Synthesis of Polysubstituted 4‐Aminoquinolines from Ynones and 2‐Aminobenzonitriles under Transition‐Metal‐Free Conditions

  摘要：

  AbstractA transition‐metal‐free and base‐promoted one‐pot reaction of ynones with 2‐aminobenzonitriles is described. The reaction was initiated through sequential aza‐Michael addition/intramolecular annulation to afford various multisubstituted 4‐aminoquinolines and 4‐amino‐1,8‐naphthyridines in good to excellent yields. Operational simplicity, high atom‐economy with broad substrate scope makes this protocol more attractive. Also, the gram‐scale synthesis and further transformation of the product were studied. Additionally, 2‐haloarylyones as substrate provide N‐arylquinolones as the sole product via the SNAr mechanism.magnified image

  DOI：

  10.1002/adsc.202100023
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-(4-methoxyphenyl)-1-(thiophen-2-yl)prop-2-yn-1-one
  参考文献：
  名称：

  Novel Microwave-Assisted One-Pot Synthesis of Isoxazoles by a Three-Component Coupling-Cycloaddition Sequence

  摘要：

  在介电加热条件下，通过羟胺酰氯现场生成的腈氧化物与末端炔烃进行连续的Sonogashira偶联，随后进行1,3-偶极环加成反应，以中等到良好的产率制备了异恶唑，实现了一种一锅法三组分反应。

  DOI：

  10.1055/s-2007-1000856

文献信息

• C–C Bond Cleavage Initiated Cascade Reaction of β-Enaminones: One-Pot Synthesis of 5-Hydroxy-1<i>H</i>-pyrrol-2(5<i>H</i>)-ones
  作者：Ting Chen、Xiujuan Zheng、Wenhua Wang、Yadong Feng、Yanyun Wang、Jinhai Shen

  DOI：10.1021/acs.joc.0c02832

  日期：2021.2.5

  C(CO)–C(Ar) bond cleavage of β-enaminones has been realized under mild and transition-metal-free conditions. The cascade transformation based on this C–C bond cleavage involves 1,3-O/C migration and aerobic hydroxylation and leads to various 5-hydroxy-1H-pyrrol-2(5H)-ones with broad functional group tolerance. The application of this methodology has been showcased by preparing 5-alkoxy-1H-pyrrol-2(5H)-one

  在温和且无过渡金属的条件下，实现了前所未有的β-烯胺酮的C（CO）-C（Ar）键裂解。基于这种C–C键断裂的级联转化涉及1,3-O / C迁移和需氧羟基化，并导致各种具有广泛官能团耐受性的5-羟基-1 H-吡咯-2（5 H）-酮。通过制备5-烷氧基-1 H-吡咯-2（5 H）-one衍生物和吡咯并[ 2,1- a ]异喹啉-3-酮衍生物展示了该方法的应用。
• A Phosphine-Mediated Synthesis of 1,4-Oxazepine- and 1,5-Oxazocine-Based Sugar Hybrids from Deoxysugar Azides¹
  作者：D. Reddy、Suresh Kurhade、Videsh Salunkhe、V. Siddaiah、Debnath Bhuniya

  DOI：10.1055/s-0030-1260218

  日期：2011.11

  An efficient and convenient method was developed for the synthesis of novel 1,4-oxazepine- and 1,5-oxazocine-based sugar hybrids from readily available deoxysugar azides by means of tributylphosphine-mediated tandem reactions. The resulting glycoconjugates might be useful in increasing the diversity of sugar backbones, and could find applications as potential glycomimetics and in drug discovery.

  通过三丁基膦介导的串联反应，研究人员开发出了一种高效便捷的方法，利用现成的脱氧糖叠氮化物合成新型的 1,4-噁氮杂环庚烷和 1,5-噁氮杂环庚烷糖基杂化物。由此产生的糖共轭物可能有助于增加糖骨架的多样性，并可作为潜在的糖模拟物应用于药物发现。
• Base-mediated ynone-isocyanide [3+2] cycloaddition: a general method to 2,3,4-tri-substituted 1-<i>H</i>-pyrroles and bis-pyrroles
  作者：Ankit Kumar、Pawan K. Mishra、Akhilesh K. Verma

  DOI：10.1039/d3cc01586f

  日期：——

  A general method for the synthesis of functionalized pyrroles and bis-pyrroles from ynones under transition-metal-free conditions in good to excellent yields has been developed.

  我们开发了一种在无过渡金属条件下从炔酮合成官能化吡咯和双吡咯的通用方法，收率良好甚至极佳。
• Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes
  作者：Heyun Sheng、Zhiwei Chen、Qiuling Song

  DOI：10.1021/jacs.3c13044

  日期：2024.1.17

  Herein, we report a ligand-controlled palladium-catalyzed method that enables the synthesis of ynones and γ-butenolides with excellent regioselectivity from the same set of readily available aryl iodides, aryl acetylenes, and BrCF2CO2K. In this reaction, the [PdII]═CF2 does demonstrate electrophilicity and can generate CO readily when reacting with H2O. It is environmentally friendly and safe compared

  在此，我们报道了一种配体控制的钯催化方法，该方法能够从同一组容易获得的芳基碘化物、芳基乙炔和 BrCF 2 CO 2 K 合成具有优异区域选择性的炔酮和 γ-丁烯内酯。在该反应中， [Pd II ]=CF 2确实表现出亲电性，与 H 2 O 反应时很容易生成 CO。与传统方法相比，它对环境友好且安全，并且当前的方案使我们能够以高产率提供炔酮和 γ-丁烯内酯出色的功能容差。此外，利用该策略还可以与相应的酚和醇获得酯。生物活性化合物后期功能化的成功进一步说明了该方案在材料开发和药物发现中的合成效用。
• Synthesis and tuberculostatic activity of S-acylvinyl-N, N-dialkyldithiocarbamates and 2-(diethylimmonium)-4-acylmethyl-4-phenyl-1, 3-dithietane perchlorates
  作者：V. N. Elokhina、A. S. Nakhmanovich、A. E. Aleksandrova、B. I. Bishnevskii、I. D. Kalikhman

  DOI：10.1007/bf01148637

  日期：1986.9