62644-49-9

Basic information

• Product Name: 6-Acetoxy-2H-pyran-3(6H)-one
• Synonyms: 2-Acetoxy-5-oxo-5,6-dihydro-2H-pyran;6-Acetoxy-2H-pyran-3(6H)-one;2H-Pyran-3(6H)-one, 6-(acetyloxy)-
• CAS NO: 62644-49-9
• Molecular Formula: C₇H₈O₄
• Molecular Weight: 156.13602
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 62644-49-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 41-42 °C
• Boiling Point: 68-87 °C(Press: 0.15 Torr)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 6-Acetoxy-2H-pyran-3(6H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Acetoxy-2H-pyran-3(6H)-one(62644-49-9)
• EPA Substance Registry System: 6-Acetoxy-2H-pyran-3(6H)-one(62644-49-9)

Safety Data

• Hazardous Substances Data: 62644-49-9(Hazardous Substances Data)

Usage

Description

6-Acetoxy-2H-pyran-3(6H)-one is an organic compound that serves as an intermediate in the synthesis of various chemical compounds. It is characterized by its yellow oil appearance and plays a crucial role in the preparation of specific molecules with unique properties and applications.

Uses

Used in Chemical Synthesis:
6-Acetoxy-2H-pyran-3(6H)-one is used as an intermediate in the preparation of 3-Methyl 2H-Furo[2,3-c]pyran-2-one (M305480), also known as "karrik". 6-Acetoxy-2H-pyran-3(6H)-one is found in smoke and is responsible for promoting seed germination, making it valuable in the agricultural industry for enhancing plant growth and development.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its role as an intermediate in chemical synthesis, 6-Acetoxy-2H-pyran-3(6H)-one may also have potential applications in the pharmaceutical industry. It could be utilized in the development of new drugs or drug candidates, particularly those targeting specific biological pathways or molecular interactions.
Used in Agricultural Industry:
6-Acetoxy-2H-pyran-3(6H)-one is used as a synthetic intermediate for the production of compounds that promote seed germination. This application is particularly relevant in the agricultural industry, where enhancing seed germination rates and plant growth can lead to increased crop yields and more sustainable farming practices.

Upstream product

• 35436-57-8 6-hydroxy-3,6-dihydro-2H-pyran-3-one 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 19969-71-2 2,5-dimethoxy-2-hydroxymethyl-2,5-dihydrofuran 
• 98-00-0 (2-furyl)methyl alcohol 
• 108-24-7 acetic anhydride 

Downstream Products

• 89189-01-5 6-endo-6-benzyloxy-8-oxabicyclo<3.2.1>oct-3-en-2-one 
• 74036-56-9 3,12-Dioxatricyclo<5.3.1.1.^2,6>dodeca-4,8-diene-10,11-dione 
• 71443-27-1 6-isopropoxy-2H-pyran-3(6H)-one 
• 71443-23-7 benzyl 2,3-dideoxy-α,β-DL-pent-2-enopyranosid-4-ulose 
• 71443-28-2 1-O-cyclohexyl-2,3-dideoxy-DL-pent-2-enopyrano-4-ulose 
• 891783-72-5 6-benzhydryloxy-dihydropyran-3-one 

Relevant articles and documents

Intermolecular Regio- and Stereoselective Hetero-[5+2] Cycloaddition of Oxidopyrylium Ylides and Cyclic Imines

We have developed the first intermolecular hetero-[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio- and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide. This new reaction provides quick access to highly substituted nitrogen-containing seven-membered rings—azepanes. Notably, a broad range of oxidopyrylium ylides and cyclic imines participate in this novel hetero-[5+2] cycloaddition reaction and the cycloadducts can be readily transformed into the core skeletons of bioactive natural products. DFT calculations revealed that the cycloaddition proceeds through a stepwise pathway and the imine nitrogen atom serves as the nucleophile to initiate the cycloaddition.

Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products

Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.

Discovery of inhibitors of the wnt and hedgehog signaling pathways through the catalytic enantioselective synthesis of an iridoid-inspired compound collection

Cousins you can count on: An iridoid-inspired compound collection was synthesized efficiently by the resolution of cyclic enones in an asymmetric cycloaddition with azomethine ylides. The collection contained novel potent inhibitors of the Wnt and Hedgehog signaling pathways. Copyright