2722-36-3

Usage

Uses

Used in Chemical Synthesis:
3-Phenyl-1-butanol is used as a reactant in the chemical synthesis industry for the production of aldehydes. It is oxidized to aldehyde using a nanoparticle-ferrite-palladium catalyst, which is a crucial step in the synthesis of various chemical compounds.
Used in Biotransformation:
In the field of biotechnology, 3-Phenyl-1-butanol is used as a substrate for biotransformation to aldehydes by oxidation in the presence of Gluconobacteroxydans DSM 2343. This process allows for the production of enantiomerically pure compounds, which are essential in the pharmaceutical and chemical industries.
Used in Enantioselective Transesterification:
3-Phenyl-1-butanol is also used as a reactant in enantioselective transesterification reactions, which are catalyzed by lipase isolated from Pseudomonas cepacia. This reaction is important for the production of optically active compounds, which have applications in the pharmaceutical, agrochemical, and fragrance industries.
Used in Flavor and Fragrance Industry:
3-Phenyl-1-butanol, due to its unique chemical structure, can be used as a building block for the synthesis of various flavor and fragrance compounds. Its ability to undergo enantioselective reactions makes it particularly valuable in creating chiral compounds with specific olfactory properties.
Used in Pharmaceutical Industry:
The enantioselective properties of 3-Phenyl-1-butanol make it a valuable compound in the pharmaceutical industry for the development of chiral drugs. These drugs can have improved efficacy and reduced side effects compared to their racemic counterparts, making them highly desirable in the development of new medications.

InChI:InChI=1/C10H14O/c1-9(7-8-11)10-5-3-2-4-6-10/h2-6,9,11H,7-8H2,1H3/t9-/m1/s1

Upstream product

• 54976-37-3 3-phenylbut-2-en-1-ol 
• 4593-90-2 3-phenylbutyric acid 
• 18826-95-4 1.3-butanediol 
• 71-43-2 benzene 
• 75-21-8 oxirane 
• 13950-05-5 α-Methylbenzyllithium 
• 1200-73-3 4-methyl-4-phenyl-1,3-dioxane 
• 1504-72-9 ethyl 3-phenylbut-2-enoate 
• 3174-83-2 3-phenylbut-3-en-1-ol 
• 16251-77-7 3-Phenylbutyraldehyde 
• 98-83-9 isopropenylbenzene 
• 7446-70-0 aluminium trichloride 
• 2203-35-2 3-chloro-1-butanol 
• 34861-81-9 diethyl phenylsuccinate 

Downstream Products

• 5801-17-2 1-bromo-3-phenylbutane 
• 13556-61-1 (3-chloro-1-methyl-propyl)-benzene 
• 2031-46-1 (R)-3-phenylbutanol 
• 16251-77-7 3-Phenylbutyraldehyde 
• 934-10-1 3-phenylbut-1-ene 
• 40283-17-8 Phosphoric acid 2,2-dichloro-vinyl ester methyl ester 3-phenyl-butyl ester 
• 159150-11-5 C₁₈H₂₃N 
• 1233222-28-0 C₂₆H₂₈N₂O₆ 
• 1236375-63-5 C₁₃H₁₈O₂ 
• 1263314-59-5 C₁₉H₂₂O₃ 
• 835-92-7 3-phenylbutyl butyrate 
• 46319-71-5 3-phenyl-1-butyl acetate 
• 432537-81-0 3-phenyl-N-(pyridin-3-ylmethyl)butanamide 
• 91404-32-9 (3-iodo-1-methyl-propyl)-benzene 

Relevant academic research and scientific papers

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride

Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.

Asymmetric Umpolung Hydrogenation and Deuteration of Alkenes Catalyzed by Nickel

Nickel-catalyzed asymmetric hydrogenation of several types of alkenes proceeds in high enantioselectivity, using acetic acid or water as the hydrogen source and indium powder as electron donor. The scope of alkenes herein include α,β-unsaturated esters, n

Catalytic Regioselective Isomerization of 2,2-Disubstituted Oxetanes to Homoallylic Alcohols

The selective isomerization of strained heterocyclic compounds is an important tool in organic synthesis. An unprecedented regioselective isomerization of 2,2-disubstituted oxetanes into homoallylic alcohols is described. The use of tris(pentafluorophenyl

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.

Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters

An unprecedented base-catalysed reductive relay hydroboration of allylic alcohols is described. Commercially available nBuLi was found to be a robust transition metal-free initiator for this protocol, affording various boronic esters in high yield and selectivity. Mechanistically, this methodology involves a one-pot three-step successive process (dehydrocoupling/allylic hydride substitution/anti-Markovnikov hydroboration).

Acid-Promoted Hydroformylative Synthesis of Alcohol with Carbon Dioxide by Heterobimetallic Ruthenium-Cobalt Catalytic System

The acid-aided heterobimetallic ruthenium-cobalt catalytic system for the reductive hydroformylation with carbon dioxide was established. Various alkenes, including waste from biomass and petroleum industry, could be upgraded to valuable alcohols with this protocol. Acid-promoted reverse water-gas shift (RWGS), thereby accelerating the hydroformylative synthesis of alcohol. The theoretical computations revealed that acid promoted RWGS by facilitating the dehydroxylation of ruthenium hydroxy carbonyl intermediate.

Palladium(II)-Catalyzed Enantioselective Arylation of Unbiased Methylene C(sp3)?H Bonds Enabled by a 2-Pyridinylisopropyl Auxiliary and Chiral Phosphoric Acids

Enantioselective functionalizations of unbiased methylene C(sp3)?H bonds of linear systems by metal insertion are intrinsically challenging and remain a largely unsolved problem. Herein, we report a palladium(II)-catalyzed enantioselective arylation of unbiased methylene β-C(sp3)?H bonds enabled by the combination of a strongly coordinating bidentate PIP auxiliary with a monodentate chiral phosphoric acid (CPA). The synergistic effect between the PIP auxiliary and the non-C2-symmetric CPA is crucial for effective stereocontrol. A broad range of aliphatic carboxylic acids and aryl bromides can be used, providing β-arylated aliphatic carboxylic acid derivatives in high yields (up to 96 %) with good enantioselectivities (up to 95:5 e.r.). Notably, this reaction also represents the first palladium(II)-catalyzed enantioselective C?H activation with less reactive and cost-effective aryl bromides as the arylating reagents. Mechanistic studies suggest that a single CPA is involved in the stereodetermining C?H palladation step.

Dual Rh?Ru Catalysts for Reductive Hydroformylation of Olefins to Alcohols

An active and selective dual catalytic system to promote domino hydroformylation–reduction reactions is described. Apart from terminal, di- and trisubstituted olefins, for the first time the less active internal C?C double bond of tetrasubstituted alkenes can also be utilized. As an example, 2,3-dimethylbut-2-ene is converted into the corresponding n-alcohol with high yield (90 %) as well as regio- and chemoselectivity (>97 %). Key for this development is the use of a combination of Rh complexes with bulky monophosphite ligands and the Ru-based Shvo's complex. A variety of aromatic and aliphatic alkenes can be directly used to obtain mainly linear alcohols.

CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes

The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.