112009-61-7

Usage

Uses

Used in Pharmaceutical Research:
(R)-1-chloro-2-hydroxy-3-phenylpropane is used as a building block in pharmaceutical research for the synthesis of various biologically active molecules. Its unique structure and functional groups contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-1-chloro-2-hydroxy-3-phenylpropane is utilized as a key intermediate for creating a diverse array of chemical compounds. Its hydroxyl and chloro groups facilitate various chemical reactions, making it a valuable component in the synthesis process.
Used in Agrochemical Production:
(R)-1-chloro-2-hydroxy-3-phenylpropane is also used in the production of agrochemicals, where its structural characteristics are leveraged to develop compounds with specific applications in agriculture, such as pesticides or herbicides.
Used in Specialty Chemicals:
Due to its unique structure and functional groups, (R)-1-chloro-2-hydroxy-3-phenylpropane can be employed in the development of specialty chemicals for various industries, including but not limited to, the chemical, pharmaceutical, and agrochemical sectors.

Upstream product

• 51594-55-9 (R)-(-)-epichlorohydrin 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 5396-65-6 1-chloro-3-phenylpropan-2-ol 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 937-38-2 1-chloro-3-phenylpropan-2-one 
• 876-27-7 4-chlorophenyl acetate 
• 591-51-5 phenyllithium 
• 145119-73-9 2-acetoxy-1-chloro-3-phenylpropane 

Downstream Products

• 112009-63-9 Carbonic acid (R)-1-azidomethyl-2-phenyl-ethyl ester tert-butyl ester 
• 406945-32-2 (R)-1-(4-{2-[Bis-(4-fluoro-phenyl)-methoxy]-ethyl}-piperazin-1-yl)-3-phenyl-propan-2-ol 
• 112009-62-8 (R)-1-azido-3-phenylpropan-2-ol 
• 20780-54-5 (S)-styrene oxide 

Relevant academic research and scientific papers

Biocatalytic deuterium- and hydrogen-transfer using over-expressed ADH-'A': Enhanced stereoselectivity and 2H-labeled chiral alcohols

Employing the over-expressed highly organic solvent tolerant alcohol dehydrogenase ADH-'A' from Rhodococcus ruber DSM 44541, versatile building blocks, which were not accessible by the wild type catalyst, were obtained in > 99% e.e.; furthermore, employing d8-2-propanol as deuterium source, stereoselective biocatalytic deuterium transfer was made feasible to furnish enantiopure deuterium labeled sec-alcohols on a preparative scale employing a single enzyme. The Royal Society of Chemistry 2006.

Pseudomonas Lipases as Catalysts in Organic Synthesis: Specificity of Lipoprotein Lipase

Described are the structural features of the substrates accepted by lipoprotein lipase from Pseudomonas aeruginosa which can serve as the rules for interpreting and predicting the specificity of this enzyme.

Diverse synthesis of the C ring fragment of bryostatins via Zn/Cu-promoted conjugate addition of α-hydroxy iodide with enone

A convergent approach to 1,5-hydroxy ketones, the general precursors for constructing the C ring of bryostatins, has been developed via a Zn/Cu-promoted conjugate addition of α-hydroxy iodides with enones. The reaction leads to direct formation of the C21-C22 bond and tolerates diverse functionalities at the C17-, C18- and C24-positions. The approach also enables a more concise synthesis of the known C ring intermediate (10 longest linear steps and 14 total steps), in contrast to its previous synthesis (17 longest linear steps and 22 total steps) in our total synthesis of bryostatin 8.

Dual DAT/σ1 receptor ligands based on 3-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-1-phenylpropan-1-ol

Ester analogs of (±)3-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-1-phenylpropan-1-ol were synthesized and evaluated for binding at DAT, SERT, NET, and σ1 receptors, and compared to GBR 12909 and several known σ1 receptor ligands. Most of these compounds demonstrated high affinity (Ki = 4.3-51 nM) and selectivity for the DAT among the monoamine transporters. S- and R-1-(4-(3-(bis(4-fluorophenyl)amino)propyl)piperazin-1-yl)-3-phenylpropan-2-ol were also prepared wherein modest enantioselectivity was demonstrated at the DAT. However, no enantioselectivity at σ1 receptors was observed and most of the ester analogs of the more active S-enantiomer showed comparable binding affinities at both DAT and σ1 receptors with a maximal 16-fold DAT/σ1 selectivity.

Stereo-complementary two-step cascades using a two-enzyme system leading to enantiopure epoxides

A novel one-pot, two-step, two-enzyme cascade is described. Pro-chiral α-chloro ketones are stereoselectively reduced to the corresponding halohydrins as an intermediate by a biocatalytic hydrogen transfer process. The intermediate is transformed to the corresponding epoxide by a non-enantioselective halohydrin dehalogenase. Thus, by combining a Prelog- or anti-Prelog alcohol dehydrogenase with a non-selective halohydrin dehalogenase, enantiopure (R)- as well as (S)-epoxides were obtained.

Non-racemic halohydrins via biocatalytic hydrogen-transfer reduction of halo-ketones and one-pot cascade reaction to enantiopure epoxides

Biocatalytic hydrogen-transfer reduction of α-chloro-ketones furnished non-racemic chlorohydrins by employing either Rhodococcus ruber as lyophilized cell catalyst or an alcohol dehydrogenase preparation from Pseudomonas fluorescens DSM 50106 (PF-ADH). Fo

Chemoenzymatic dynamic kinetic resolution of β-halo alcohols. An efficient route to chiral epoxides

Enzymatic resolution of β-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when β-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation of the enzyme. The synthetic utility of this procedure has been illustrated by the practical synthesis of different chiral epoxides.

Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: Chiral hydroxyl-containing derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy) ethyl]-4-(3-ph

In our search for long-acting agents for the treatment of cocaine abuse, a series of optically pure hydroxylated derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (1) and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)pip

ALKYLATION OF 2-PHENYLSULFINYLETHANOL

Alkylation of 2-phenylsulfinylethanol resulted syndiastereomer as the major products, although the ratio of syn/anti isomers varied depending on the alkyl group.By application of this prodeure to the chiral sulfoxides, optically active epoxides have been obtained in good yields.