71309-70-1

Basic information

• Product Name: 3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN
• Synonyms: 3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN
• CAS NO: 71309-70-1
• Molecular Formula: C₈H₁₆O₂Si
• Molecular Weight: 172.3
• Mol File: 71309-70-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 62-65 °C/10 mmHg(lit.)
• Flash Point: 28 °C
• Appearance: /
• Density: 0.94 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.433(lit.)
• CAS DataBase Reference: 3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN(71309-70-1)
• EPA Substance Registry System: 3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN(71309-70-1)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: 1993
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 71309-70-1(Hazardous Substances Data)

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 603-76-9 1-methylindole 
• 1621232-92-5 trimethyl(6,7,8,9-tetrachloro-4a-(2,3,4,5-tetrachloro-6-(trimethylsilyloxy)phenoxy)-3,4,4a,10a-tetrahydro-2H-benzo[b]pyrano[2,3-e][1,4]dioxin-10a-yloxy)silane 
• 1621232-85-6 2,3,5-trifluoro-6-(2-oxotetrahydro-2H-pyran-3-yl)cyclohexa-2,5-diene-1,4-dione 
• 1621232-82-3 3-(2,3,5,6-tetrachloro-4-hydroxyphenoxy)tetrahydro-2H-pyran-2-one 
• 1621232-84-5 2,3,5-Trichloro-6-(2-oxotetrahydro-2H-pyran-3-yl)cyclohexa-2,5-diene-1,4-dione 
• 1621232-72-1 3-(2,5-dichloro-3,6-dihydroxyphenyl)tetrahydro-2H-pyran-2-one 
• 1621232-67-4 3-(2,5-dihydroxyphenyl)tetrahydro-2H-pyran-2-one 
• 501698-85-7 3-(hydroxydiphenylmethyl)tetrahydropyran-2-one 
• 1443013-68-0 (S)-α-(4-acetylphenyl)-δ-valerolactone 
• 1443013-71-5 (S)-α-(α-styryl)-δ-valerolactone 

Relevant articles and documents

A simple thiophosphate-based method for α-alkylidenation of lactones

A variety of α-alkylidene lactones has been synthesized using a one-pot procedure based on the reaction of readily available thiophosphates with aldehydes under basic, mild conditions. Georg Thieme Verlag Stuttgart.

Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation

An electrophilic trifluoromethylation of ketene silyl acetals (KSAs) by hypervalent iodine reagents 1 and 2 has been developed. The reaction proceeds under very mild conditions in the presence of a catalytic amount of trimethylsilyl bis(trifluoromethanesulfonyl)imide (up to 2.5 mol %) as a Lewis acid providing a direct access to a variety of secondary, tertiary, and quaternary α-trifluoromethyl esters and lactones in high yield (up to 98%).

Synthetic studies towards the core structure of nakadomarin a by a thioamide-based strategy

The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon-carbon bond-forming reaction between a furan and an N-acyliminium ion derived from a secondary thiolactam. In addition, a novel three-component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported. Two key steps in a projected total synthesis of nakadomarin A have been realised by using the unique chemistry of thioamides. Formation of the carbocyclic B ring can be effected by nucleophilic attack of a furan on a thiolactam-derived iminium ion, and the key quaternary centre can be established by a novel three-component coupling reaction.

A stereoselective cyclisation cascade mediated by SmI2-H 2O: Synthetic studies towards stolonidiol

A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemoselective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol.