77693-46-0

Basic information

• Product Name: 1-methyl-4-[(1S)-1-methylprop-2-en-1-yl]benzene
• Synonyms: 1-methyl-4-[(1S)-1-methylprop-2-en-1-yl]benzene
• CAS NO: 77693-46-0
• Molecular Weight: 146.232
• Mol File: 77693-46-0.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 1-methyl-4-[(1S)-1-methylprop-2-en-1-yl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-4-[(1S)-1-methylprop-2-en-1-yl]benzene(77693-46-0)
• EPA Substance Registry System: 1-methyl-4-[(1S)-1-methylprop-2-en-1-yl]benzene(77693-46-0)

Safety Data

• Hazardous Substances Data: 77693-46-0(Hazardous Substances Data)

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 74-85-1 ethene 
• 54636-56-5 (E)-1-(3-bromoprop-1-en-1-yl)-4-methylbenzene 
• 75-16-1 methylmagnesium bromide 
• 54636-56-5 3-bromo-1-p-tolyl-1-propene 
• 201230-82-2 carbon monoxide 
• 1394035-47-2 (2E)-but-2-en-1-yl 4-(trifluoromethyl)phenyl ether 
• 5720-05-8 4-methylphenylboronic acid 
• 96000-21-4 (E)-p-methylcinnamyl chloride 
• 593-60-2 Vinyl bromide 
• 77693-45-9 1-(p-tolyl)ethylmagnesium chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 58824-48-9 1-(4-methylphenyl)-2-propen-1-ol 

Relevant articles and documents

Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation

Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt-catalyzed hydrovinylation as the chirogenic step. Other noteworthy C?C bond forming transformations include diastereoselective Lewis acid-mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4-methyl-styrene the anti-tubercular agent (+)-erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti-inflammatory activity (inhibition of LPS-induced NF-κB activation) as a natural mixture of pseudopterosins A?D or iso-pseudopterosin A, prepared by β-D-xylosylation of the synthetic aglycone.

Copper-free asymmetric allylic alkylation with a grignard reagent: Design of the ligand and mechanistic studies

The Cu-free asymmetric allylic alkylation, catalysed by NHC, with Grignard reagents is reported on allyl bromide derivatives with good results. The enantioselectivity was quite homogeneous (around 85 % ee) on large and various substrates, regardless of the nature of the Grignard reagent. The formation of stereogenic quaternary centres was highly regioselective for both aliphatic and aromatic derivatives with good enantiomeric excess (up to 92 % ee). The methodology developed was found to be complementary with the Cu-catalysed version. Several new NHCs were tested with improved efficiency. In addition, mechanistic studies, using NMR spectroscopy, led to the discovery of the catalytically active species. Copyright

Rhodium-catalyzed asymmetric coupling reaction of allylic ethers with arylboronic acids

An asymmetric allylic substitution of simple allylic ethers with arylboronic acids in the presence of a rhodium(I)/(R)-DTBM-SEGPHOS catalyst has been developed. The reactions proceeded smoothly at room temperature to give the corresponding branch products with excellent regioselectivities and good to excellent enantioselectivities.