(R)-1-phenylethyl acetate

Base Information

• Chemical Name: (R)-1-phenylethyl acetate
• CAS No.: 16197-92-5
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• DSSTox Substance ID: DTXSID001315000
• Nikkaji Number: J56.781G
• Mol file: 16197-92-5.mol

Synonyms:(R)-1-phenylethyl acetate;16197-92-5;Acetic acid, (1R)-1-phenylethyl ester;1-Phenylethyl acetate #;[(1R)-1-phenylethyl] acetate;1R-Styrallyl acetate;(+)-Styrallyl acetate;starbld0001154;SCHEMBL2292807;Acetic acid (R)-1-phenylethyl;DTXSID001315000;(1R)-1-PHENYLETHYL ACETATE;Acetic acid, 1-(R)-phenylethyl ester

Chemical Property of (R)-1-phenylethyl acetate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)OC(=O)C
• Isomeric SMILES: C[C@H](C1=CC=CC=C1)OC(=O)C

Technology Process of (R)-1-phenylethyl acetate

There total 152 articles about (R)-1-phenylethyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

Isopropyl acetate (108-21-4) + 1-Phenylethanol (98-85-1,13323-81-4) → (R)-1-phenethyl acetate (16197-92-5) + acetophenone (98-86-2)

Guidance literature:

With Candida antarctica lipase B; potassium tert-butylate; [(η²-C6H4-o-CH2NH2)Ru(NCMe)(η⁶-p-cymene)]PF6; In dodecane; toluene; at 70 ℃; for 48h; under 210.021 Torr;

DOI:10.1002/adsc.200700379

Reference yield: 85.0%

1-acetoxy-1-phenylethene (2206-94-2) → 1-Phenylethanol (98-85-1,13323-81-4) + (R)-1-phenethyl acetate (16197-92-5) + acetophenone (98-86-2)

Guidance literature:

With Novozym 435; 2,6-dimethyl-4-heptanol; (Ph4C4CO)2H(μ-H)(CO)4Ru2; In toluene; at 70 ℃; for 42h; Enzymatic reaction;

DOI:10.1021/ol9914043

Reference yield: 30.0%

ethyl acetate (141-78-6) + acetophenone (98-86-2) → ethylbenzene (100-41-4,27536-89-6) + (R)-1-phenethyl acetate (16197-92-5)

Guidance literature:

With 4 wt % Ru/Al2O3; (2 wt % Pd + 5 wt % Zn)/Al2O3; hydrogen; In toluene; at 70 ℃; for 6h; under 760.051 Torr; optical yield given as %ee; stereoselective reaction; Enzymatic reaction;

DOI:10.1134/S0023158411010095

upstream raw materials:

(R)-1-phenylethanol

acetic anhydride

acetyl chloride

2-acetoxypyridine

Downstream raw materials:

1-phenylethyl formate

1-(2-(butyltellanyl)phenyl)ethanol

(R)-butyl(2-(1-methoxyethyl)phenyl)tellane

(R)-4,4,5,5-tetramethyl-2-(2-phenylbutan-2-yl)-1,3,2-dioxaborolane

Refernces

• 1、 Dominguez De Maria, Pablo,Sinisterra Gago, Jose V.. "Causes of unreproducibility of C. rugosa Lipase-catalyzed reactions in slightly hydrated organic media". . p. 8555 - 8566. Retrieved 1999.
• 2、 Yazicio?lu, Emre Y.,Tanyeli, Cihangir. "A method for the synthesis of pyridine-based C2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling". . p. 1694 - 1699. Retrieved 2012.
• 3、 Reetz, Manfred T.,Eipper, Andreas,Tielmann, Patrick,Mynott, Richard. "A Practical NMR-Based High-Throughput Assay for Screening Enantioselective Catalysts and Biocatalysts". . p. 1008 - 1016. Retrieved 2002.
• 4、 Larsson,Persson,Backvall. "Enzymatic resolution of alcohols coupled with ruthenium-catalyzed racemization of the substrate alcohol". . p. 1211 - 1212. Retrieved 1997.
• 5、 Katritzky, Alan R.,Ou, Yu Xiang,Musumarra, Giuseppe. "Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 12. Regio- and Stereo-chemistry of Nucleophilic Displacement and Solvolysis Reactions of N(α-Methylallyl)- and N-(α-Phenylethyl)-pyridiniums". . p. 1449 - 1454. Retrieved 1983.
• 6、 Tielmann, Patrick,Boese, Matthias,Luft, Martin,Reetz, Manfred T.. "A practical high-throughput screening system for enantioselectivity by using FTIR spectroscopy". . p. 3882 - 3887. Retrieved 2003.
• 7、 Koszelewski, Dominik,Brodzka, Anna,Madej, Arleta,Trzepizur, Damian,Ostaszewski, Ryszard. "Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols". . p. 6331 - 6342. Retrieved 2021/05/06.
• 8、 Kinens, Artis,Balkaitis, Simonas,Ahmad, Omar K.,Piotrowski, David W.,Suna, Edgars. "Acylative Dynamic Kinetic Resolution of Secondary Alcohols: Tandem Catalysis by HyperBTM and B?ckvall's Ruthenium Complex". . p. 7189 - 7202. Retrieved 2021/05/29.