1504-71-8

Usage

Uses

Used in Pharmaceutical Industry:
(E)-3-(2-chloro-phenyl)-prop-2-en-1-ol is used as an intermediate in the synthesis of pharmaceuticals. Its chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of medical treatments.
Used in Fragrance and Flavor Industry:
(E)-3-(2-CHLORO-PHENYL)-PROP-2-EN-1-OL serves as a building block in the production of fragrances and flavors. Its unique properties enable the creation of a wide range of scents and tastes, enhancing the sensory experience of various products.
Used in Agrochemical Industry:
(E)-3-(2-chloro-phenyl)-prop-2-en-1-ol is also utilized in the agrochemical sector, where it plays a role in the development of pesticides and other agricultural chemicals. Its contribution to this industry helps improve crop protection and yield.
Used as a Reagent in Organic Synthesis:
In the field of organic chemistry, (E)-3-(2-chloro-phenyl)-prop-2-en-1-ol acts as a valuable reagent. Its reactivity and stability make it suitable for various organic synthesis processes, facilitating the creation of new compounds and materials.
Used as a Solvent in Industrial Processes:
Furthermore, (E)-3-(2-CHLORO-PHENYL)-PROP-2-EN-1-OL is employed as a solvent in different industrial processes. Its ability to dissolve a wide range of substances makes it a useful tool in various manufacturing and production applications.
Precaution:
It is important to handle (E)-3-(2-chloro-phenyl)-prop-2-en-1-ol with care, as it can cause skin and eye irritation. Additionally, it may be harmful if ingested or inhaled, necessitating proper safety measures during its use and storage.

Upstream product

• 1794-45-2 2-chlorocinnamaldehyde 
• 24393-51-9 ethyl 3-(2-chlorophenyl)acrylate 
• 89-98-5 2-chloro-benzaldehyde 
• 75-07-0 acetaldehyde 
• 42174-97-0 3-(2-chloro-phenyl)-acrylic acid methyl ester 
• 58824-52-5 α-vinyl-o-chlorobenzyl alcohol 

Downstream Products

• 1507-92-2 o-chlorocinnamyl chloride 
• 1193844-18-6 [(1S,2S,3R)-2-(2-chlorophenyl)-3-phenylcyclopropyl]methanol 
• 1186634-64-9 o-chlorophenylallyl methyl carbonate 
• 15542-32-2 (2E,4E)-5-(2-chlorophenyl)penta-2,4-dienoic acid 
• 960355-42-4 ethyl 5-(2-chloro-phenyl)-penta-2,4-dienoate 

Relevant academic research and scientific papers

In Situ Acetaldehyde Synthesis for Carboligation Reactions

The enzyme 4-oxalocrotonate tautomerase (4-OT) can promiscuously catalyze various carboligation reactions using acetaldehyde as a nucleophile. However, the highly reactive nature of acetaldehyde requires intricate handling, which can impede its usage in practical synthesis. Therefore, we investigated three enzymatic routes to synthesize acetaldehyde in situ in one-pot cascade reactions with 4-OT. Two routes afforded practical acetaldehyde concentrations, using an environmental pollutant, trans-3-chloroacrylic acid, or a bio-renewable, ethanol, as starting substrate. These routes can be combined with 4-OT catalyzed Michael-type additions and aldol condensations in one pot. This modular systems biocatalysis methodology provides a stepping stone towards the development of larger artificial metabolic networks for the practical synthesis of important chemical synthons.

Ternary Catalysis Enabled Three-Component Asymmetric Allylic Alkylation as a Concise Track to Chiral α,α-Disubstituted Ketones

Multicomponent reactions that involve interception of onium ylides through Aldol, Mannich, and Michael addition with corresponding bench-stable acceptors have demonstrated broad applications in synthetic chemistry. However, because of the high reactivity and transient survival of these in situ generated intermediates, the substitution-type interception process, especially the asymmetric catalytic version, remains hitherto unknown. Herein, a three-component asymmetric allylation of α-diazo carbonyl compounds with alcohols and allyl carbonates is disclosed by employing a ternary cooperative catalysis of achiral Pd-complex, Rh2(OAc)4, and chiral phosphoric acid CPA. This method represents the first example of three-component asymmetric allylic alkylation through an SN1-type trapping process, which involves a convergent assembly of two active intermediates, Pd-allyl species, and enol derived from onium ylides, providing an expeditious access to chiral α,α-disubstituted ketones in good to high yields with high to excellent enantioselectivity. Combined experimental and computational studies have shed light on the mechanism of this novel three-component reaction, including the critical role of Xantphos ligand and the origin of enantioselectivity.

Boron-Catalyzed C?C Functionalization of Allyl Alcohols

Tris(pentafluorophenyl)borane-catalyzed C?C bond functionalization of arylallyl alcohols using donor-acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal-free transformation presents a novel disconnection strategy towards carbon-carbon bond scission and formation. (Figure presented.).

Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water

The pH-dependent selective Ir-catalyzed hydrogenation of α,β-unsaturated aldehydes was realized in water. Using HCOOH as the hydride donor at low pH, the unsaturated alcohol products were obtained exclusively, while the saturated alcohol products were formed preferentially by employing HCOONa as the hydride donor at high pH. A wide range of functional groups including electron-rich as well as electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.

Gold-Catalyzed [2,3]-Sigmatropic Rearrangement: Reaction of Aryl Allyl Alcohols with Diazo Compounds

A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rearrangement occurs between in situ generated donor-acceptor gold-carbenes and cinnamyl alcohols via tandem oxonium ylide formation. The desired rearranged product has been accomplished selectively over more conventional O-H insertion, cyclopropanation, cycloaddition, and C-H functionalization products under mild, open-air conditions. The scope of the work has been illustrated by synthesizing a new class of substrates that can be used for constructing complex molecular targets.

Expanding the substrate scope of phenylalanine ammonia-lyase from: Petroselinum crispum towards styrylalanines

This study focuses on the expansion of the substrate scope of phenylalanine ammonia-lyase from Petroselinum crispum (PcPAL) towards the l-enantiomers of racemic styrylalanines rac-1a-d-which are less studied and synthetically challenging unnatural amino acids-by reshaping the aromatic binding pocket of the active site of PcPAL by point mutations. Ammonia elimination from l-styrylalanine (l-1a) catalyzed by non-mutated PcPAL (wt-PcPAL) took place with a 777-fold lower kcat/KM value than the deamination of the natural substrate, l-Phe. Computer modeling of the reactions catalyzed by wt-PcPAL indicated an unproductive and two major catalytically active conformations and detrimental interactions between the aromatic moiety of l-styrylalanine, l-1a, and the phenyl ring of the residue F137 in the aromatic binding region of the active site. Replacing the residue F137 by smaller hydrophobic residues resulted in a small mutant library (F137X-PcPAL, X being V, A, and G), from which F137V-PcPAL could transform l-styrylalanine with comparable activity to that of the wt-PcPAL with l-Phe. Furthermore, F137V-PcPAL showed superior catalytic efficiency in the ammonia elimination reaction of several racemic styrylalanine derivatives (rac-1a-d) providing access to d-1a-d by kinetic resolution, even though the d-enantiomers proved to be reversible inhibitors. The enhanced catalytic efficiency of F137V-PcPAL towards racemic styrylalanines rac-1a-d could be rationalized by molecular modeling, indicating the more relaxed enzyme-substrate complexes and the promotion of conformations with higher catalytic activities as the main reasons. Unfortunately, ammonia addition onto the corresponding styrylacrylates 2a-d failed with both wt-PcPAL and F137V-PcPAL. The low equilibrium constant of the ammonia addition, the poor ligand binding affinities of 2a-d, and the non-productive binding states of the unsaturated ligands 2a-d within the active sites of either wt-PcPAL or F137V-PcPAL-as indicated by molecular modeling-might be responsible for the inactivity of the PcPAL variants in the reverse reaction. Modeling predicted that the F137V mutation is beneficial for the KRs of 4-fluoro-, 4-cyano- and 4-bromostyrylalanines, but non-effective for the KR process of 4-trifluoromethylstyrylalanine.

Catalytic asymmetric bromochlorination of aromatic allylic alcohols promoted by multifunctional Schiff base ligands

It was found that the tridentate O,N,O-type Schiff base ligand bearing suitable substituents was a highly effective promoter in the catalytic asymmetric bromochlorination reaction, in which the corresponding aromatic bromochloroalcohols with vicinal halogen-bearing stereocenters were formed with perfect regioselectivity, with moderate to excellent enantioselectivities (up to 93% ee), and with good yields and chemoselectivities.