105836-13-3

Usage

Uses

Used in Fragrance Industry:
(R)-1-(2-Methoxyphenyl)propanol is used as a fragrance ingredient for its capacity to contribute a floral, woody scent to perfumes, colognes, and other cosmetic products. Its unique odor profile allows it to enhance the overall aroma of these products, providing a more complex and appealing scent to consumers.
Used in Flavor Industry:
In the food industry, (R)-1-(2-Methoxyphenyl)propanol is utilized as a flavoring agent. Its ability to modify and enhance the taste of various products makes it a valuable addition to the flavorist's toolbox, allowing for the creation of more nuanced and enjoyable flavors in the food and beverage sector.
Used in Research and Experimental Studies:
(R)-1-(2-Methoxyphenyl)propanol has also found application in research and experimental studies, particularly those related to olfactory perception and sensory analysis. Its distinct odor characteristics make it an interesting subject for scientists and researchers looking to better understand how humans perceive and process different scents.
Safety Precautions:
While (R)-1-(2-Methoxyphenyl)propanol has various applications, it is important to note that it may cause skin and eye irritation. Therefore, proper handling and storage protocols should be followed, including using the compound in a well-ventilated area to minimize potential health risks.

Upstream product

• 612-16-8 (2-methoxyphenyl)methanol 
• 557-20-0 diethylzinc 
• 5561-92-2 1-(2-methoxyphenyl)propan-1-one 
• 97-93-8 triethylaluminum 
• 135-02-4 ortho-anisaldehyde 
• 10467-10-4 ethylmagnesium iodide 

Downstream Products

• 123820-56-4 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-(2-methoxy-phenyl)-propyl ester 

Relevant academic research and scientific papers

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Pyrolidine and Piperidine γ-Amino Alcohols

The enantioselective alkylation of aryl aldehydes by diethylzinc in the presence of catalytic amounts of several chiral pyrolidine- and piperidine-based amino alcohol ligands, synthesized from the reaction of (R)-2-amino-1-butanol and (S)-2-amino-3-phenylpropan-1-ol with appropriate dibromoalkanes, was studied. The influence f temperature and ligand structure has been investigated. Addition of diethylzinc to aromatic aldehydes under the optimized condition gave the corresponding products in excellent yields with ee values of up to 77%.

C3 Symmetric oxazolinyl ligand as catalyst in the enantioselective addition of diethylzinc to aldehydes

The C3 symmetric oxazolinyl ligand 1 has been synthesized. Compound 1 catalyzed the addition of diethylzinc to aromatic aldehydes to give secondary alcohols with high enantiomeric excesses (up to 90%).

Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium(IV) complexes of N-sulfonylated amino alcohols with two stereogenic centers

Bidentate N-sulfonylated amino alcohols with one or two stereogenic centers were prepared and applied as chiral ligands in the titanium(IV)-catalyzed asymmetric addition of diethylzinc to aldehydes, affording excellent enantioselectivities of up to 98% e.e.

Enantioselective carbon-carbon bond forming reactions using fluorous chiral catalysts

Fluorous chiral BINOLs and BINAP were prepared and used as the ligands for an asymmetric addition of Et2Zn to aromatic aldehydes and an asymmetric Heck reaction, respectively. The enantioselectivities were similar in homogeneous system to those of the original non-fluorous reactions. Consecutive reactions were examined by utilizing fluorous-organic biphase and fluorous solid phase extraction techniques. Enantioselectivities in consecutive reactions were close to that attained in the non-fluorous system. The solid phase extraction method also enabled us to perform a simultaneous screening procedure.

Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols

A series of o-xylylene-type 1,4-amino alcohols, synthesized from (R)-1-phenylethylamine, were used as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde. (S)-1-Phenyl-1-propanol was obtained with high enantioselectivity in all cases since the stereochemical outcome of the reaction was controlled by the chiral benzylic carbon bearing amino group. Highest catalytic activity was obtained by using (R)-1-{2-[1-(pyrrolidin-1-yl)ethyl]phenyl}cyclohexan-1-ol (1n) derived from (R)-1-(1-phenylethyl)pyrrolidine and cyclohexanone. Various chiral secondary alcohols were obtained by the reaction of diethylzinc and aldehydes in the presence of 1n within 2 h with good to high enantioselectivities.

Chiral ligands for asymmetric synthesis: Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral N-α-pyridylmethyl amino alcohols

A series of chiral ligands 2a-d were conveniently prepared from τ-amino alcohols through a two-step sequence and applied to catalysis of enantioselective addition of diethylzinc to benzaldehyde. Among them ligand 2c was found to show the best asymmetric induction for the reaction and catalyze the addition to various aromatic aldehydes to provide (R)-secondary alcohols in up to 98.3% ee. (C) 2000 Elsevier Science Ltd.

High Catalytic Activity of Chiral Amino Alcohol Ligands Anchored to Polystyrene Resins

Enantiomerically pure (2S,3S)-2,3-epoxy-3-phenylpropanol (3) has been anchored to Merrifield resins with different degrees of cross-linking and functionalization. The resulting epoxy-functionalized resins 4 have been submitted to completely regioselective

Straightforward access to chiral diol bidentate ligands: Their efficient enantioselective induction in the addition of diethylzinc to aromatic aldehydes

Enantiopure C2-symmetric diol bidentate ligands have been synthesized in a straightforward manner through a three-step reaction with good yields. The synthesized C2-symmetric diol bidentate ligands were used in the addition of diethylzinc to various aromatic aldehydes, a general catalytic benchmark reaction, in order to assess their enantioselective induction properties. The enantioselective addition of diethylzinc to 1-naphthaldehyde and 3-chlorobenzaldehyde was achieved with an enantiomeric excess (ee) of up to 98%. All synthesized ligands were also evaluated in the addition of diethyzinc to aromatic aldehydes including an extra metal such as Ti(IV) (up to 99% ee).

Enantioselective addition of diethylzinc to aldehydes in the presence of chiral hydrazone and imine ligands

Optically active hydrazone and imine were found to act as effective ligands for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with ee up to 71%.

Synthesis of N-Alkylated and N-Arylated Derivatives of 2-Amino-2′-hydroxy-l, 1′-binaphthyl (NOBIN) and 2,2′-Diamino-1, 1′'-binaphthyl and Their Application in the Enantioselective Addition of Diethylzinc to Aromatic Aldehydes a

High-yield reductive alkylation of CR)-(+)-l and (R)-(+)-2 has been accomplished with a series of ketones (even as bulky as 2-adamantanone) and NaBH4/H2SO4 in THF at room temperature to give the respective N-alkylated binaphthyls 6a-c, 9a-c, and 10a-c. Related W-phenyl derivatives 14, 16, and 17 were obtained via the Pd(0)-catalyzed coupling of (R)-(+)-l and (R)-(+)-2, respectively, with PhBr; no racemization was observed. Subsequent reductive methylation with CH2O and NaBH4/H2SO4 afforded the bidentate ligands 8a-c, 12a-c, 13a-c, 15, 18, and 19, which comprise a new class of binaphthyls. Their utility as chiral ligands has been demonstrated for the addition of Et2Zn to benzaldehyde and its congeners; the highest level of asymmetric induction was observed for N.N-dimethyl NOBIN (R)-(+)-3 (3 mol %) in conjunction with n-BuLi (5.4 mol %), which gave CR)-(+)-21a in 88% ee. Derivatives of the amino phenol 1 (NOBIN) proved more efficient than the corresponding diamines derived from 2. The stereochemical outcome and the enhancement of asymmetric induction by Li+ are discussed in terms of the chelated transition state 26.