42070-92-8

Usage

Uses

Used in Fragrance Industry:
(R)-1-(4-Methylphenyl)ethyl alcohol is used as a fragrance ingredient for its refreshing minty and herbal scent, contributing to the aroma profiles of perfumes, soaps, and other personal care products.
Used in Flavor and Food Additive Production:
(R)-1-(4-Methylphenyl)ethyl alcohol serves as a key component in the creation of flavors and food additives, enhancing the taste and aroma of various food products.
Used in Natural Products:
(R)-1-(4-Methylphenyl)ethyl alcohol is used as a natural alternative in the formulation of products, leveraging its derivation from mint oils to provide a genuine and eco-friendly scent and flavor profile.

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 86561-30-0 1-(4-methylphenyl)ethyl acetate 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 17279-31-1 (-)-(S)-N,N-dimethyl-1-phenylethylamine 
• 108-24-7 acetic anhydride 
• 122-00-9 para-methylacetophenone 
• 544-97-8 dimethyl zinc(II) 
• 104-87-0 4-methyl-benzaldehyde 
• 622-96-8 4-methylethylbenzene 
• 464-78-8 (1S)-(+)-ketopinic acid 
• 108-22-5 Isopropenyl acetate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-05-4 vinyl acetate 
• 137203-34-0 bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct 

Downstream Products

• 622852-35-1 2,3,4,5,6-pentafluoro-benzoic acid 1-p-tolyl-ethyl ester 
• 1016275-05-0 C₁₄H₁₆N₂O₂ 
• 1415088-79-7 phenyl[1-(4-tolylethyl)]selane 
• 1616889-22-5 C₉H₁₁Cl 
• 586-70-9 (R)-4'-methyl-1-phenylethylamine 
• 122-00-9 para-methylacetophenone 
• 120121-02-0 (3,5-Dinitro-phenyl)-carbamic acid (R)-1-p-tolyl-ethyl ester 
• 1195962-55-0 (E)-1-((R)-1-p-tolylethoxy)-2-methylpent-1-en-3-one 
• 1415088-78-6 phenyl[1-(4-tolylethyl)]selane 
• 24344-85-2 (+)-1-(4'-methylphenyl)bromoethane 
• 152336-38-4 C₁₂H₁₆O₂ 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 84194-74-1 (R)-1-(p-tolyl)ethyl acetate 

Relevant academic research and scientific papers

Synthesis, coordination behavior, and structural features of chiral amino-, pyrazolyl-, and phosphino-substituted ferrocenyloxazolines and their application in asymmetric hydrogenations

A highly flexible and modular synthesis of 15 chiral nonracemic ferrocenyloxazolines-all based on a ferrocenylethyl backbone-is described. Starting from N,N-dimethylaminoethyl ferrocene a range of oxazoline derivatives with various oxazoline substituents were prepared in a three-step sequence. After reaction with methyl iodide, the quaternized dimethylamino group was replaced by different amino, pyrazolyl, and phosphinyl groups. Subsequent reduction of the phosphinyl groups gave phosphinooxazoline derivatives. The molecular structures of three palladium [PdCl2(L)] and three ruthenium [RuCl(p-cymene)(L)]PF6 complexes of representative ferrocenyloxazoline ligands were studied by X-ray diffraction. In addition, five ruthenium complexes [RuCl2(PPh3)(L)] were prepared. These complexes were tested, using a high-throughput screening system, in the asymmetric hydrogenation of three ketones. Enantioselectivities of up to 99% ee were obtained.

Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

The asymmetric total synthesis of fasicularin is reported. The key to success is the use of a chiral N-alkoxyamide to control both reactivity and stereoselectivity. This functional group enables the aza-spirocyclization and the reductive Strecker reaction

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.

Chiral Yolk-Shell MOF as an Efficient Nanoreactor for Asymmetric Catalysis in Organic-Aqueous Two-Phase System

It remains a great challenge to introduce large and efficient homogeneous asymmetric catalysts into MOFs and other microporous materials as well as retain their degrees of freedom. Herein, a new heterogeneous strategy of homogeneous chiral catalysts is proposed, that is, to construct a yolk-shell MOFs-confined, large-size, and highly efficient homogeneous chiral catalyst, which can be used as a nanoreactor for asymmetric catalytic reactions.

2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes

A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α′-CF3-diol ligand was highlighted in the ZnII-catalyzed asymmetric ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes. Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcohols in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). As observed from single crystal diffraction analysis, the complexation of the 2,2′-bipyridine-α,α′-CF3-diol ligand generates an unusual hexacoordinated ZnII.

Exploration of highly electron-rich manganese complexes in enantioselective oxidation catalysis; A focus on enantioselective benzylic oxidation

The direct enantioselective hydroxylation of benzylic C-H bonds to form chiral benzylic alcohols represents a challenging transformation. Herein, we report on the exploration of new biologically inspired manganese and iron complexes bearing highly electron-rich aminopyridine ligands containing 4-pyrrolidinopyridine moieties ((S,S)-1, (R,R)-1, 2 and 5) in combination with chiral bis-pyrrolidine and N,N-cyclohexanediamine backbones in enantioselective oxidation catalysis with aqueous H2O2. The current manganese complexes outperform the analogous manganese complexes containing 4-dimethylaminopyridine moieties (3 and 4) in benzylic oxidation reactions in terms of alcohol yield while keeping similar ee values (～60% ee), which is attributed to the higher basicity of the 4-pyrrolidinopyridine group. A detailed investigation of different carboxylic acid additives in enantioselective benzylic oxidation provides new insights into how to rationally enhance enantioselectivities by means of proper tuning of the environment around the catalytic active site, and has resulted in the selection of Boc-l-Tert-leucine as the preferred additive. Using these optimized conditions, manganese complex 2 was shown to be effective in the enantioselective benzylic oxidation of a series of arylalkane substrates with up to 50% alcohol yield and 62% product ee. A final set of experiments also highlights the use of the new 4-pyrrolidinopyridine-based complexes in the asymmetric epoxidation of olefins (up to 98% epoxide yield and >99% ee).

Synthesis, characterization and catalytic performance in enantioselective reactions by mesoporous silica materials functionalized with chiral thiourea-amine ligand

Chiral heterogeneous catalysts have been synthesized by grafting of silyl derivatives of (1R, 2R)- or (1S, 2S)-1,2-diphenylethane-1,2-diamine on SBA-15 mesoporous support. The mesoporous material SBA-15 and so-prepared chiral heterogeneous catalysts were characterized by a combination of different techniques such as X-ray diffractometry (XRD), Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), field emission scanning electron microscopy (FESEM), and Brunauer–Emmett–Teller (BET) surface area. Results showed that (1R, 2R)- and (1S, 2S)-1,2-diphenylethane-1,2-diamine were successively immobilized on SBA-15 mesoporous support. Chiral heterogeneous catalysts and their homogenous counterparts were tested in enantioselective transfer hydrogenation of aromatic ketones and enantioselective Michael addition of acetylacetone to β-nitroolefin derivatives. The catalysts demonstrated notably high catalytic conversions (up to 99%) with moderate enantiomeric excess (up to 30% ee) for the heterogeneous enantioselective transfer hydrogenation. The catalytic performances for enantioselective Michael reaction showed excellent activities (up to 99%) with poor enantioselectivities. Particularly, the chiral heterogeneous catalysts could be readily recycled for Michael reaction and reused in three consecutive catalytic experiments with no loss of catalytic efficacies.

Method for synthesizing chiral secondary alcohol compound

The invention discloses a method for synthesizing a chiral secondary alcohol compound. The method comprises the following step of: reacting a ketone compound in an aprotic organic solvent at room temperature and inert gas atmosphere under the action of a chiral cobalt catalyst and an activating agent by taking a combination of bis(pinacolato)diboron and alcohol or water as a reducing agent to obtain the chiral secondary alcohol compound. According to the method disclosed by the invention, a combination of pinacol diborate and alcohol or water which are cheap, stable and easy to obtain is taken as a reducing agent, and a ketone compound is efficiently reduced to synthesize a corresponding chiral secondary alcohol compound in an aprotic organic solvent under the action of a chiral cobalt catalyst; in a chiral cobalt catalyst adopted by the method, when a chiral ligand is PAOR, an activating agent is NaBHEt3 or NaOtBu and an adopted raw material is aromatic ketone, the yield is 80% or above, and the optical purity is 90% or above; and when the adopted raw material is alkane ketone, the yield can reach 70% or above, and the optical purity can reach 80% or above.

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.