4-chloro-7-methoxy-2-oxo-2H-chromene-3-carbaldehyde | 122978-33-0

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-chloro-7-methoxy-2-oxo-2H-chromene-3-carbaldehyde
• 英文别名: 4-chloro-7-methoxy-2-oxochromene-3-carbaldehyde
• CAS: 122978-33-0
• 化学式: C₁₁H₇ClO₄
• 分子量: 238.627
• InChiKey: ISMYIGLBVUWLBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-7-methoxy-2-oxo-2H-chromene-3-carbaldehyde 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三溴化硼 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ES517
  参考文献：
  名称：

  ExoSensor 517: A Dual-Analyte Fluorescent Chemosensor for Visualizing Neurotransmitter Exocytosis

  摘要：

  A dual-analyte fluorescent chemosensor (ExoSensor 517) for the direct visualization of neurotransmitters released upon exocytosis is presented. The sensor exploits the high concentration of neurotransmitters (e.g., glutamate, norepinephrine, and dopamine) and the pH gradient between the vesicle and synaptic cleft. The cooperative recognition elements require both binding and a change in environmental pH to afford a fluorescence response which makes ExoSensor 517 one of the first integrated molecular logic gates to be used for biological applications.

  DOI：

  10.1021/cn400128s
• 作为产物：
  描述：

  丹皮酚 在 sodium hydride 、 三氯氧磷 作用下， 以 三氯乙烯 、 mineral oil 为溶剂， 反应 30.5h， 生成 4-chloro-7-methoxy-2-oxo-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Thienochromene derivatives inhibit pSTAT1 and pSTAT5 signaling induced by cytokines

  摘要：

  Furanocoumarins, particularly furo[3,2-c]coumarins, are found in many natural products. However, coumarins annulated to a thiophene ring have received scarce attention to date in the literature. Therefore, we synthesized 4-oxo-4H-thieno [3,2-c] chromene derivatives and tested in vitro their anti-inflammatory activity. Anti-inflammatory potential of the synthesized compounds (1, 2, 6-8, 9a-e and 10a-c) has been evaluated by measuring various pSTAT (signal transducer and activator of transcription) inhibition within the JAK (Janus-activated family kinase)/STAT signaling pathway. Ethyl 7-hydroxy-4-oxo-4H-thieno[3,2-cichromene-2-carboxylate (7) showed best inhibition properties on pSTAT5 in GM-CSF (Granulocyte-macrophage colony-stimulating factor)-triggered PBMC assay, with IC50 value of 5.0 mu M.

  DOI：

  10.1016/j.bmcl.2020.127415

文献信息

• Pd-Catalyzed cross-coupling synthesis of 4-aryl-3-formylcoumarins
  作者：Maddali L. N. Rao、Sachchida Nand

  DOI：10.1039/d1ob02016a

  日期：——

  The threefold cross-coupling of triarylbismuth reagents with 4-chloro-3-formylcoumarins furnished the corresponding 4-aryl-3-formylcoumarins in a chemoselective manner with high yields under Pd-catalyzed conditions. This method was successfully applied to electronically different triarylbismuth reagents and 4-chloro-3-formylcoumarins preserving the 3-formyl group in the coumarin scaffold.

  三芳基铋试剂与 4-氯-3-甲酰基香豆素的三重交叉偶联以化学选择性方式在 Pd 催化条件下以高产率提供了相应的 4-芳基-3-甲酰基香豆素。该方法成功地应用于电子不同的三芳基铋试剂和保留香豆素支架中3-甲酰基的4-氯-3-甲酰基香豆素。
• Base-Dependent Divergent Annulation of 4-Chloro-3-formylcoumarin and Tetrahydroisoquinoline: Application to the Synthesis of Isolamellarins and Hydroxypyrrolones
  作者：Sameer Vyasamudri、Ding-Yah Yang

  DOI：10.1021/acs.joc.8b03259

  日期：2019.3.15

  coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1-a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give

  一系列吡咯并[2,1- a ]异喹啉和香豆素稠合的五环衍生物是通过4-氯-3-甲酰基香豆素和四氢异喹啉的碱介导的发散环化反应合成的，这是关键步骤。然后将该方法扩展到制备异烯丙三醇酯A和B（异麦角菌素G三甲基醚）。当暴露于紫外线下时，发现吡咯并[2,1- a ]异喹啉和香豆素融合的五环B发生有氧氧化，生成相应的羟基吡咯烷酮。
• Light/inductive effect induced isomerization of chromeno-5-methyl-2,6,9-trioxabicyclo[3.3.1]nonadienes
  作者：Sameer Vyasamudri、Ding-Yah Yang

  DOI：10.1039/d0nj02288h

  日期：——

  Light-mediated [1,3] sigmatropic shift of chromeno-5-methyl-2,6,9-trioxabicyclo[3.3.1]nonadienes to yield chromeno-3-methyl-2,6,9-trioxabicyclo[3.3.1]nonadienes was reported. The migration was observed to proceed without the requirement of UV light if a strong electron-withdrawing group on the benzene moiety or a strong electron-donating group on the coumarin moiety is present. A plausible stepwise

  铬诺-5-甲基-2,6,9-三恶双环[3.3.1]壬二烯的光介导[1,3]σ位移产生铬诺-3-甲基-2,6,9-三恶双环[3.3.1]报告了壬二烯。如果在苯部分上有一个强吸电子基团或在香豆素部分上有一个给电子基团，则观察到迁移是在不需要紫外线的情况下进行的。对于后者的异构化，提出了合理的逐步离子机理。
• Three-component synthesis of pyran-fused biscoumarins: an entry to pyridinone- and pyranone-fused coumarins
  作者：Jui-Ting Lee、Nagesh Jatangi、Sameer Vyasamudri、Ding-Yah Yang

  DOI：10.1039/d4ra01681e

  日期：——

  three-component synthesis of symmetric and unsymmetric pyran-fused biscoumarins via the coupling of 4-hydroxycoumarin with 4-chloro-3-formylcoumarin in ethanol is reported. This methodology is further extended to the construction of various indole/coumarin-substituted symmetric pyran-fused biscoumarins. The unsymmetric pyran-fused biscoumarin can react with amines and 4-hydroxycoumarins under basic and acidic

  报道了通过4-羟基香豆素与 4-氯-3-甲酰基香豆素在乙醇中偶联，碱介导的三组分合成对称和不对称吡喃稠合双香豆素。该方法进一步扩展到各种吲哚/香豆素取代的对称吡喃稠合双香豆素的构建。不对称吡喃稠合双香豆素可以在碱性和酸性条件下与胺和4-羟基香豆素反应，分别得到吡啶酮稠合香豆素和吡喃酮稠合香豆素。提出了它们的形成机制。
• Weissenfels, Manfred; Hantschmann, Achim; Steinfuehrer, Thorsten, Zeitschrift fur Chemie, 1989, vol. 29, # 5, p. 166
  作者：Weissenfels, Manfred、Hantschmann, Achim、Steinfuehrer, Thorsten、Birkner, Eckhard

  DOI：——

  日期：——