80006-87-7

Basic information

• Product Name: Propanoic acid, 2,2-dimethyl-, (2E)-3-phenyl-2-propenyl ester
• CAS NO: 80006-87-7
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• Mol File: 80006-87-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 2,2-dimethyl-, (2E)-3-phenyl-2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2,2-dimethyl-, (2E)-3-phenyl-2-propenyl ester(80006-87-7)
• EPA Substance Registry System: Propanoic acid, 2,2-dimethyl-, (2E)-3-phenyl-2-propenyl ester(80006-87-7)

Safety Data

• Hazardous Substances Data: 80006-87-7(Hazardous Substances Data)

Upstream product

• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 3282-30-2 pivaloyl chloride 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 75-98-9 Trimethylacetic acid 
• 18997-19-8 Chloromethyl pivalate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 300-57-2 allylbenzene 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 
• 1184-88-9 sodium pivalate 
• 673-32-5 1-Phenylprop-1-yne 

Downstream Products

• 16215-11-5 trans-cinnamyl p-tolyl sulfone 
• 1401467-22-8 (R)-methyl 2,2-dimethyl-3-phenylpent-4-enoate 
• 20068-10-4 (E)-4-phenyl-3-butenenitrile 
• 1076-66-0 3-phenyl-1,5-hexadiene 
• 56644-04-3 (E)-1-phenyl-1,5-hexadiene 
• 108400-97-1 ethyl (4E)-2-acetyl-5-phenylpent-4-enoate 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 

Relevant articles and documents

Enantioselective synthesis of acyclic allylic esters catalyzed by a palladium/BINAP(S) system

The synthesis of chiral nonracemic acyclic allylic pivalates via the Pd-catalyzed allylic substitution of racemic allylic carbonates is presented. Good to excellent enantioselectivities (up to 90%) were observed in several cases. An extraordinarily high preference for the production of the branched regioisomeric product is seen when starting from 3-buten-2-yl and crotyl substrates. A significant kinetic resolution (krel = 38) of the 1,3-dimethylallyl substrate was also observed, leading to the production of esters of both enantiomers of an allylic alcohol with a single enantiomer of catalyst.

Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.

Disubstituted Z-allylic esters by Wittig-Schlosser reaction using methylenetriphenylphosphorane

β-Lithiooxyphosphonium ylides, generated in situ from aldehydes and methylenetriphenylphosphorane, react with halomethyl esters to form disubstituted allylic esters in good yields and with high Z-selectivity.