145439-09-4

Basic information

• Product Name: 4-Tributylstannyl-5H-furan-2-one
• Synonyms: 4-Tributylstannyl-5H-furan-2-one
• CAS NO: 145439-09-4
• Molecular Formula: C16H30O2Sn
• Molecular Weight: 373.121
• Product Categories: Stannanes
• Mol File: 145439-09-4.mol

Chemical Properties

• Boiling Point: 395.581°C at 760 mmHg
• Flash Point: 193.04°C
• Appearance: /
• Vapor Pressure: 0mmHg at 25°C
• CAS DataBase Reference: 4-Tributylstannyl-5H-furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Tributylstannyl-5H-furan-2-one(145439-09-4)
• EPA Substance Registry System: 4-Tributylstannyl-5H-furan-2-one(145439-09-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 145439-09-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
4-Tributylstannyl-5H-furan-2-one is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals. The presence of the tributylstannyl group on the furan ring allows for the introduction of the furan moiety into more complex molecules through cross-coupling reactions, enhancing the compound's versatility in organic synthesis.
Used in Organic Synthesis:
4-Tributylstannyl-5H-furan-2-one is used as a versatile reagent in organic synthesis for various transformations. The tin atom attached to the furan ring makes it a potential candidate for further functionalization or modification, enabling the creation of more complex molecules and compounds.

InChI:InChI=1/C4H3O2.3C4H9.Sn/c5-4-2-1-3-6-4;3*1-3-4-2;/h2H,3H2;3*1,3-4H2,2H3;/rC16H30O2Sn/c1-4-7-10-19(11-8-5-2,12-9-6-3)15-13-16(17)18-14-15/h13H,4-12,14H2,1-3H3

Upstream product

• 31555-05-2 methyl 4-hydroxy-2-butynoate 
• 688-73-3 tri-n-butyl-tin hydride 
• 56634-50-5 4-bromo-5H-furan-2-one 
• 813-19-4 bis(tri-n-butyltin) 

Downstream Products

• 81052-99-5 cleviolide 
• 155140-39-9 4-iodo,2(5H)-furanone 

Relevant articles and documents

A New Insight into the Stereoelectronic Control of the Pd0-Catalyzed Allylic Substitution: Application for the Synthesis of Multisubstituted Pyran-2-ones via an Unusual 1,3-Transposition

Pyran-2-ones 3 undergo a novel Pd0-catalyzed 1,3-rearrangement to afford isomers 6. The reaction proceeds via an η2-Pd complex, the pyramidalization of which (confirmed by quantum chemistry calculations) offers a favorable antiperiplanar alignment of the Pd?C and allylic C?O bonds (C), thus allowing the formation of an η3-Pd intermediate. Subsequent rotation and rate-limiting recombination with the carboxylate arm then gives isomeric pyran-2-ones 6. The calculated free energies reproduce the observed kinetics semi-quantitatively.

Enantioselective Total Synthesis of Cannogenol-3-O-α- l -rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions

A concise and scalable enantioselective total synthesis of the natural cardenolides cannogenol and cannogenol-3-O-α-l-rhamnoside has been achieved in 18 linear steps. The synthesis features a Cu(II)-catalyzed enantioselective and diastereoselective Michae