32466-45-8

Basic information

• Product Name: (2R)-6-methoxy-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromene
• CAS NO: 32466-45-8
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 444.7327
• Mol File: 32466-45-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 518.3°C at 760 mmHg
• Flash Point: 144°C
• Density: 0.91g/cm³
• Vapor Pressure: 2.48E-10mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: (2R)-6-methoxy-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromene(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-6-methoxy-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromene(32466-45-8)
• EPA Substance Registry System: (2R)-6-methoxy-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromene(32466-45-8)

Safety Data

• Hazardous Substances Data: 32466-45-8(Hazardous Substances Data)

Upstream product

• 60018-13-5 (+)-dihydrocitronellal 
• 105857-90-7 (R)-4,8-dimethylnon-1-ene 
• 101515-38-2 (2R,6R,10R)-2,6,10,14-Tetramethylpentadecan-1,2-diol 
• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 65528-01-0 (3R,7R)-3,7,11-trimethyl-dodecyl bromide 

Downstream Products

• 59-02-9 Tocopherol 
• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 

Relevant articles and documents

Total synthesis of (R,R,R)-α-tocopherol through asymmetric cu-catalyzed 1,4-addition

By introducing a disposable activating substituent at C-3, the asymmetric 1,4-addition to a notoriously unreactive 2-substituted chromenone was achieved with high levels of (2R)-stereoselectivity in the presence of a chiral CuI-phosphoramidite

Total Synthesis of α-Tocopherol through Enantioselective Iridium-Catalyzed Fragmentation of a Spiro-Cyclobutanol Intermediate

A conceptionally new strategy for the asymmetric (2R-selective) synthesis of α-tocopherol (vitamin E) was developed. In the stereocontrolled key step, a prochiral spiro[chromane-2,3′-cyclobutanol] unit is effectively desymmetrized under C?C bond activation in an unprecedented iridium-catalyzed transformation using (S)-DTBM-SegPhos as a chiral ligand (e.r. 97:3). To complete the synthesis, the side chain was attached through Ru-catalyzed cross-metathesis employing an alkene derived from (R,R)-hexahydrofarnesol. To suppress epimerization during the final hydrogenation, PtO2 had to be used as a catalyst instead of Pd/C. In an alternative approach (employing a propargyl-substituted spiro-cyclobutanol), the side chain was constructed prior to the Ir-catalyzed ring fragmentation (>99:1 d.r.) through enyne cross-metathesis (using an alkene derived from (R)-dihydrocitronellal) followed by Cr-catalyzed 1,4-hydrogenation and (diastereoselective) Pfaltz hydrogenation of the resulting triple-substituted olefin. The work demonstrates the potential of iridium catalysis for enantioselective C?C bond activation.

SYNTHESIS OF CHROMANE COMPOUNDS AND THEIR DERIVATIVES BY A COPPER-CATALYZED CONJUGATE ADDITION REACTION

The present invention relates to the preparation of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction. It has been observed that in highly stereoselective manner a methyl group can be introduced to the 2 position o