198561-42-1

Basic information

• Product Name: (R)-3-acetyloxy-3-phenylpropanenitrile
• Synonyms: (R)-3-acetyloxy-3-phenylpropanenitrile
• CAS NO: 198561-42-1
• Molecular Weight: 189.214
• Mol File: 198561-42-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (R)-3-acetyloxy-3-phenylpropanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-acetyloxy-3-phenylpropanenitrile(198561-42-1)
• EPA Substance Registry System: (R)-3-acetyloxy-3-phenylpropanenitrile(198561-42-1)

Safety Data

• Hazardous Substances Data: 198561-42-1(Hazardous Substances Data)

Upstream product

• 876-27-7 4-chlorophenyl acetate 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 108-22-5 Isopropenyl acetate 
• 108-24-7 acetic anhydride 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 
• 96-09-3 styrene oxide 
• 108-05-4 vinyl acetate 
• 82782-11-4 (+/-)-3-acetyloxy-3-phenylpropanenitrile 

Downstream Products

• 24506-17-0 ethyl (R)-3-hydroxy-3-phenylbutanoate 
• 191733-30-9 (S)-N-(ethoxycarbonyl)-3-(4-(trifluoromethyl)phenoxy)-3-phenyl-1-propanamine 
• 191733-29-6 (S)-N-(ethoxycarbonyl)-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine 
• 191733-28-5 (S)-N-(ethoxycarbonyl)-3-(2-methylphenoxy)-3-phenyl-1-propanamine 
• 502697-62-3 (R)-(3-hydroxy-3-phenylpropyl)carbamic acid ethyl ester 
• 130194-43-3 (R)-Norfluoxetine 
• 112066-66-7 (S)-N-methyl-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine 
• 105314-53-2 (S)-N-methyl-3-(2-methylphenoxy)-3-phenyl-1-propanamine 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 
• 100568-02-3 (S)-fluoxetine 
• 54910-89-3 (R)-fluoxetine 
• 138750-31-9 (1R)-3-amino-1-phenyl-1-propanol 
• 1885-38-7 cinnamic nitrile 

Relevant articles and documents

Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions

Aluminium triflate (0.01-0.1 mol %) was found to be an efficient catalyst for the acylation of alcohols, phenols, thiols and sugars with acetic anhydride in high yields under solvent-free conditions in a short reaction time at room temperature. Racemization of optically active alcohols and epimerization of sugars were not observed. The acylation efficacy of various acyl donors was also investigated.

Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles

A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alcohol and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C 'Amano' II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.

Study of the enantioselectivity of the CAL-B-catalysed transesterification of α-substituted α-propylmethanols and α-substituted benzyl alcohols

A study of the enantioselectivity exhibited by the lipase B from Candida antarctica in the transesterification of different α-substituted α-propylmethanols with vinyl acetate is shown. The best results are obtained when the large-sized (L) substituent of the alcohol is either a phenyl group or more especially a cyclohexyl group, although the reaction rates are lower than when linear or slightly branched groups are present. It is also found that ramification at the β-position of the L substituent has a deleterious effect on both lipase activity and enantioselectivity. Moreover, some α-substituted benzyl alcohols bearing medium-sized (M) substituents larger than an ethyl and smaller than a propyl group are resolved by means of this methodology with moderate-good enantioselectivities (E=46-57) and similar reaction rates.