2-(4-methoxyphenyl)-4,7-dimethylthieno[3,2-b]pyridin-5(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 2-(4-methoxyphenyl)-4,7-dimethylthieno[3,2-b]pyridin-5(4H)-one
• 英文别名: 2-(4-Methoxyphenyl)-4,7-dimethylthieno[3,2-b]pyridin-5-one；2-(4-methoxyphenyl)-4,7-dimethylthieno[3,2-b]pyridin-5-one
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: IKWHGYMKAOCKLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 5-bromo-3-(methylamino)thiophene-2-carboxylate 在 四(三苯基膦)钯 、 silica gel 、 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 2-(4-methoxyphenyl)-4,7-dimethylthieno[3,2-b]pyridin-5(4H)-one
  参考文献：
  名称：

  荧光硫杂[3,2 - b ]吡啶-5（4 H）-ones的合成，分子工程和光物理性质

  摘要：

  我们描述了一套荧光thieno [3,2 - b ]吡啶-5（4 H）-衍生物及其光物理性质的合成方法。这些荧光团是通过一系列使用铃木-宫浦交叉偶联反应和3-氨基噻吩与α，β-不饱和羧酸的区域选择性氮杂-[3 + 3]环加成反应制备的。我们的研究结果表明，光物理性质是由官能团上的噻吩并[3,2-一个合适的选择化学可调b ]吡啶5（4 ħ） -酮支架。

  DOI：

  10.1021/acs.joc.8b01924

文献信息

• NOVEL THIENO[3,2-B]PYRIDINE-5(4H)-ONE DERIVATIVE COMPOUND, PREPARATION METHOD THEREOF AND USE THEREOF
  申请人：Korea Institute of Ocean Science & Technology

  公开号：US20210171539A1

  公开（公告）日：2021-06-10

  The present invention relates to a novel thieno[3,2-b]pyridine-5(4H)-one derivative compound, a preparation method thereof, and a use thereof. The novel thieno[3,2-b]pyridine-5(4H)-one derivative compound according to the present invention is synthesized via an aza-[3+3] cyclization addition reaction using BOP, wherein the compound is obtained by synthesizing a 4-arylthiophen-3-amine in which aryl groups such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4 are introduced via a synthesis process by a bromination reaction, a hydrolysis reaction, a decarboxylation reaction, and a Suzuki coupling reaction of methyl 3-aminothiophene carboxylate, and by synthesizing 4-arylthiophen-3-amine and mono-methyl fumarate via a formal aza-[3+3] cyclization addition reaction using BOP and conjugation. Accordingly, novel thieno[3,2-b]pyridine-5(4H)-one derivative compounds according to the present invention have fluorescence properties with a wide range of emission wavelengths and thus may be utilized in various industrial fields such as physics, chemistry, and biomedical research.

  本发明涉及一种新型噻吩[3,2-b]吡啶-5(4H)-酮衍生物化合物，其制备方法及用途。根据本发明，所述新型噻吩[3,2-b]吡啶-5(4H)-酮衍生物化合物是通过使用BOP进行一种aza-[3+3]环化加成反应合成的，其中该化合物是通过合成一种4-芳基噻吩-3-胺获得的，其中芳基基团如4-哌啶基-C6H4、4-吡咯基-C6H4、4-MeOC6H4、3,4,5-(MeO)3C6H4、C6H5、4-C6H5C6H4和4-F3COC6H4等通过溴化反应、水解反应、脱羧反应和甲基3-氨基噻吩羧酸酯的铂催化偶联反应的合成过程引入，通过使用BOP和共轭进行形式aza-[3+3]环化加成反应合成4-芳基噻吩-3-胺和单甲基富马酸。因此，根据本发明，所述新型噻吩[3,2-b]吡啶-5(4H)-酮衍生物化合物具有广泛的发射波长范围的荧光性能，因此可以应用于物理学、化学和生物医学研究等各种工业领域。
• METHOD FOR SYNTHESIZING THIENO[3,2-B]PYRIDINE-5(4H)-ONE DERIVATIVE COMPOUND, USING GOLD CATALYST, AND USE THEREFOR
  申请人：Korea Institute of Ocean Science & Technology

  公开号：US20210332063A1

  公开（公告）日：2021-10-28

  Disclosed are a method for synthesizing a thieno[3,2-b]pyridine-5(4H)-one derivative by using a gold catalyst and a use of the derivative compound, wherein the novel thieno[3,2-b]pyridine-5(4H)-one derivative of the present disclosure, which is a compound synthesized using gold as a catalyst, has fluorescence characteristics with a wide range of emission wavelengths and thus can be helpfully used in various industrial fields, such as physics, chemistry, and biomedicine research.

  本发明揭示了一种使用金催化剂合成噻吩[3，2-b]吡啶-5（4H）-酮衍生物的方法以及该衍生物化合物的用途。本发明的新型噻吩[3，2-b]吡啶-5（4H）-酮衍生物是使用金作为催化剂合成的化合物，具有广泛的发射波长范围的荧光特性，因此可以在物理学、化学和生物医学研究等各种工业领域中得到有益的应用。
• Thieno[3,2-b]pyridine-5(4H)-one derivative compound, preparation method thereof and use thereof
  申请人：Korea Institute of Ocean Science & Technology

  公开号：US11306103B2

  公开（公告）日：2022-04-19

  The present invention relates to a novel thieno[3,2-b]pyridine-5(4H)-one derivative compound, a preparation method thereof, and a use thereof. The novel thieno[3,2-b]pyridine-5(4H)-one derivative compound according to the present invention is synthesized via an aza-[3+3] cyclization addition reaction using BOP, wherein the compound is obtained by synthesizing a 4-arylthiophen-3-amine in which aryl groups such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4 are introduced via a synthesis process by a bromination reaction, a hydrolysis reaction, a decarboxylation reaction, and a Suzuki coupling reaction of methyl 3-aminothiophene carboxylate, and by synthesizing 4-arylthiophen-3-amine and mono-methyl fumarate via a formal aza-[3+3] cyclization addition reaction using BOP and conjugation. Accordingly, novel thieno[3,2-b]pyridine-5(4H)-one derivative compounds according to the present invention have fluorescence properties with a wide range of emission wavelengths and thus may be utilized in various industrial fields such as physics, chemistry, and biomedical research.

  本发明涉及一种新型噻吩并[3,2-b]吡啶-5(4H)-酮衍生物化合物、其制备方法及其用途。根据本发明的新型噻吩并[3,2-b]吡啶-5(4H)-酮衍生物化合物是利用 BOP 通过氮杂-[3+3]环化加成反应合成的、其中，该化合物是通过合成 4-芳基噻吩-3-胺得到的，其中芳基如 4-哌啶基-C6H4、4-吡咯烷基-C6H4、4-MeOC6H4、3,4,5-(MeO)3C6H4、C6H5、4-C6H5C6H4、和 4-F3COC6H4 是通过 3-氨基噻吩羧酸甲酯的溴化反应、水解反应、脱羧反应和铃木偶联反应的合成过程，以及通过使用 BOP 和共轭的形式偶氮-[3+3] 环化加成反应合成 4-芳基噻吩-3-胺和富马酸单甲酯的过程引入的。因此，根据本发明的新型噻吩并[3,2-b]吡啶-5(4H)-酮衍生物化合物具有发射波长范围广的荧光特性，因此可用于各种工业领域，如物理学、化学和生物医学研究。
• Gold(I)-Catalyzed Intramolecular Hydrothiophenylation of <i>N</i>-Thiophen-3-yl Alkynylamides for Accessing Thieno[3,2-<i>b</i>]pyridine-5(4<i>H</i>)-ones: Development of F-Actin Specific Fluorescent Probes
  作者：Dan-Bi Sung、Jang Hee Han、Yong-Keon Kim、Bo Hyun Mun、Sol Park、Hyun Seok Kim、Jong Seok Lee

  DOI：10.1021/acs.joc.1c02923

  日期：2022.4.1
• [EN] METHOD FOR SYNTHESIZING THIENO[3,2-B]PYRIDINE-5(4H)-ONE DERIVATIVE COMPOUND, USING GOLD CATALYST, AND USE THEREFOR<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'UN COMPOSÉ DÉRIVÉ DE THIÉNO[3,2-B]PYRIDINE-5(4H)-ONE À L'AIDE D'UN CATALYSEUR D'OR, ET UTILISATION ASSOCIÉE<br/>[KO] 금 촉매를 이용한 티에노［３，２-ｂ］피리딘-５（４Ｈ）-온 유도체 화합물의 합성방법 및 이들 유도체 화합물의 용도
  申请人：KOREA INST OCEAN SCI & TECH

  公开号：WO2020036243A1

  公开（公告）日：2020-02-20

  본 발명은 금 촉매를 이용한 티에노[3,2-b] 피리딘-5(4H)-온 유도체 화합물의 합성방법 및 상기 유도체 화합물의 용도에 관한 것으로, 본 발명의 신규 티에노[3,2-b] 피리딘-5(4H)-온 유도체 화합물은 금을 촉매로 사용하여 합성된 화합물은 광범위한 영역의 방출파장을 갖는 형광특성을 가지므로 물리, 화학, 바이오의료 연구 등 다양한 산업분야에서 유용하게 사용할 수 있다.