Pyridin-2-yl furan-2-carboxylate | 505067-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: Pyridin-2-yl furan-2-carboxylate
• CAS: 505067-85-6
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: WVZLVAXLMUWLJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Pyridin-2-yl furan-2-carboxylate 、 苯硼酸 在 potassium phosphate 、 Pd/α-Al2O3 、 钯 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以85%的产率得到2-呋喃基苯基酮
  参考文献：
  名称：

  通过化学选择性 C(酰基)-O 键激活杂芳基酯的异质 Suzuki-Miyaura 偶联†

  摘要：

  开发了一种以杂芳基酯和芳基硼酸为偶联伙伴的位点选择性负载钯纳米颗粒催化的 Suzuki-Miyaura 交叉偶联反应。该方法通过成功抑制不需要的脱羰现象，通过酯的 C(酰基)-O 键活化，为芳基酮的形成提供了一种多相催化途径。该催化剂可重复使用，并在八次循环后表现出较高的活性。反应前后催化剂的XPS分析表明该反应可能是通过以Pd 0开始的Pd 0 /Pd II催化循环进行的。

  DOI：

  10.1039/c9ra02394a
• 作为产物：
  描述：

  2-羟基吡啶 、 呋喃甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Pyridin-2-yl furan-2-carboxylate
  参考文献：
  名称：

  Structure–activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors

  摘要：

  Human rhinovirus 3C protease (HRV 3C(pro)) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3C(pro), a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3C(pro), to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.114

文献信息

• Difluorocarbene-Triggered Acyl Rearrangement Reaction: A Strategy for the Direct Introduction of the <i>gem</i>-Difluoromethylene Group
  作者：Haitao Cui、Caijin Ban、Fengting Zhu、Jingmei Yuan、Juan Du、Yanmin Huang、Qi Xiao、Chusheng Huang、Jun Huang、Qiang Zhu

  DOI：10.1021/acs.orglett.2c03907

  日期：2023.1.13

  A novel metal- and catalyst-free dearomative reaction of 2-oxypyridines to construct gem-difluoromethylenated N-substituted 2-pyridones has been developed. The reaction involves an attractive acyl rearrangement from O to CF2 of difluorocarbene-derived pyridinium ylides, which provides a new strategy for the direct introduction of the gem-difluoromethylene group with high efficiency and selectivity as

  开发了一种新型的无金属和无催化剂的 2-氧吡啶脱芳烃反应，用于构建偕-二氟亚甲基化的 N-取代 2-吡啶酮。该反应涉及二氟卡宾衍生的吡啶鎓叶立德从O到CF 2的吸引性酰基重排，为直接引入偕-二氟亚甲基提供了一种高效、选择性好、底物适用范围广的新策略。还证明了克级合成和合成转化。
• Difluorocarbene enabled ester insertion/1,4-acyl rearrangement of 2-acetoxylpyridines: Modular access to gem-difluoromethylenated 2-pyridones
  作者：Shi-Wei Li、Gang Wang、Zhi-Shi Ye

  DOI：10.1016/j.tetlet.2023.154413

  日期：2023.4

  An efficient and simple protocol for the construction of gem-difluoromethylenated 2-pyridones via difluorocarbene enabled ester insertion/acyl rearrangement of 2-acetoxylpyridines and (bromodifluoromethyl)trimethylsilane has been documented. The reactions feature transition-metal free, mild reaction conditions and excellent functional group compatibility. The late-stage modification of bioactive molecules

  已经记录了一种有效且简单的方案，用于通过二氟卡宾构建宝石- 二氟亚甲基化 2-吡啶酮，使 2-乙酰氧基吡啶和（溴二氟甲基）三甲基硅烷的酯插入/酰基重排成为可能。该反应不含过渡金属，反应条件温和，官能团相容性好。生物活性分子的后期修饰、放大反应和合成转化证明了该协议的实用性。
• Rh(II)-Catalyzed Synthesis of <i>N</i>-Aryl 2-pyridone Using 2-Oxypyridine and Diazonaphthoquinone Via 1,6-Benzoyl Migratory Rearrangement
  作者：Subarna Pan、Suparna Kundu、Rajarshi Samanta

  DOI：10.1021/acs.orglett.3c00854

  日期：2023.4.28
• Heterogeneous Suzuki–Miyaura coupling of heteroaryl ester <i>via</i> chemoselective C(acyl)–O bond activation
  作者：Hongpeng Ma、Chaolumen Bai、Yong-Sheng Bao

  DOI：10.1039/c9ra02394a

  日期：——

  A site-selective supported palladium nanoparticle catalyzed Suzuki–Miyaura cross-coupling reaction with heteroaryl esters and arylboronic acids as coupling partners was developed. This methodology provides a heterogeneous catalytic route for aryl ketone formation via C(acyl)–O bond activation of esters by successful suppression of the undesired decarbonylation phenomenon. The catalyst can be reused

  开发了一种以杂芳基酯和芳基硼酸为偶联伙伴的位点选择性负载钯纳米颗粒催化的 Suzuki-Miyaura 交叉偶联反应。该方法通过成功抑制不需要的脱羰现象，通过酯的 C(酰基)-O 键活化，为芳基酮的形成提供了一种多相催化途径。该催化剂可重复使用，并在八次循环后表现出较高的活性。反应前后催化剂的XPS分析表明该反应可能是通过以Pd 0开始的Pd 0 /Pd II催化循环进行的。
• Structure–activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors
  作者：Isak Im、Eui Seung Lee、Soo Jeong Choi、Ju-Yeon Lee、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2009.04.114

  日期：2009.7

  Human rhinovirus 3C protease (HRV 3C(pro)) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3C(pro), a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3C(pro), to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket. (C) 2009 Elsevier Ltd. All rights reserved.