535924-69-7

Basic information

• Product Name: 4-Tributylstannyl-3,6-dihydro-2H-pyran
• Synonyms: 4-Tributylstannyl-3,6-dihydro-2H-pyran;tributyl(3,6-dihydro-2H-pyran-4-yl)stannane
• CAS NO: 535924-69-7
• Molecular Formula: C₁₇H₃₄OSn
• Molecular Weight: 373.16126
• Mol File: 535924-69-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 376.5±52.0 °C(Predicted)
• Appearance: /
• CAS DataBase Reference: 4-Tributylstannyl-3,6-dihydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Tributylstannyl-3,6-dihydro-2H-pyran(535924-69-7)
• EPA Substance Registry System: 4-Tributylstannyl-3,6-dihydro-2H-pyran(535924-69-7)

Safety Data

• Hazardous Substances Data: 535924-69-7(Hazardous Substances Data)

Usage

General Description

4-Tributylstannyl-3,6-dihydro-2H-pyran is a chemical compound with the molecular formula C21H40OSn. It is a stannane derivative of 3,6-dihydro-2H-pyran, which is a versatile building block in organic synthesis. The tributyltin group in the compound makes it useful in organic reactions as a source of the tributylstannyl group. It is commonly used as a reagent in organic synthesis for the functionalization of organic molecules, such as in the preparation of vinyl stannanes, which can then be used in cross-coupling reactions. The compound is also used in the synthesis of biologically active compounds and in the development of pharmaceuticals. However, its use has declined in recent years due to concerns about the environmental and health impacts of organotin compounds.

Upstream product

• 29943-42-8 Tetrahydro-4H-pyran-4-one 

Downstream Products

• 1174765-16-2 3-[4-(3,6-dihydro-2H-pyran-4-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenol 
• 1174766-18-7 tert-butyl 4-(4-(3,6-dihydro-2H-pyran-4-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylcarbamate 
• 1197164-56-9 8-(4-(3,6-dihydro-2H-pyran-4-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane 
• 1421357-84-7 (S)-(5-(2-(3,6-dihydro-2H-pyran-4-yl)-4-(3-methylmorpholinyl)pyrido[2,3-d]pyrimidine-7-yl)2-methoxyphenyl)methanol 
• 1421357-83-6 (S)-(2-methoxy-5-(4-(3-methylmorpholine)-2-(tetrahydro-2H-pyran-4-yl)pyrido[2,3-d]pyrimidin-7-yl)phenyl)methanol 
• 1417617-59-4 4-(4-methyl-3-nitrophenyl)-3,6-dihydro-2H-pyran 
• 1250868-62-2 8-[6-(3,6-dihydro-2H-pyran-4-yl)-2-(4-nitrophenyl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane 
• 1202041-81-3 4-(2,4-dichlorophenyl)-2-(3,6-dihydro-2H-pyran-4-yl)-5-(4H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile 
• 208465-06-9 C₂₄H₂₆N₂O₂ 

Relevant articles and documents

Flow Photo-Nazarov Reactions of 2-Furyl Vinyl Ketones: Cyclizing a Class of Traditionally Unreactive Heteroaromatic Enones

Nazarov reactions of 2-furyl vinyl ketones and related heteroaromatic enones, to produce furan-fused cyclopentanones using a flow photochemical approach, are described. Compounds possessing this connectivity between heterocycle and ketone (2-furyl, 2-benzofuryl, 2-thiophene-yl, and 2-benzothiophene-yl) have traditionally proven difficult or impossible to cyclize with typical Br?nsted and Lewis acid mediated methods. Using mild flow photochemistry conditions and acetic acid (AcOH) or hexafluoroisopropanol (HFIP) as solvent, these compounds were found to cyclize in 45-97% yields, with typical UV exposure times of 3.4-6.8 min. In all cases, 2-furyl and 2-thiophene-yl enones cyclized, whereas 2-benzofuryl and 2-benzothiophene-yl enones exhibited divergent properties with reactivity patterns tied to the identity of the vinyl group. This report discloses the first photo-Nazarov reactions of tetrahydropyridine-substituted 2-furyl ketones, providing a direct approach to the corresponding fused heterocyclic motifs built around a central cyclopentanone. These motifs constitute the core structures of biologically active natural products, including the marine alkaloid nakadomarin A.