27993-56-2

Usage

Synthesis Reference(s)

Synthesis, p. 980, 1988 DOI: 10.1055/s-1988-27774

InChI:InChI=1/C8H7ClO2/c9-7-3-1-6(2-4-7)8(11)5-10/h1-4,10H,5H2

Upstream product

• 90273-33-9 2-Oxo-2-(4-chlorophenyl)ethyl formate 
• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 58518-76-6 ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane 
• 99-91-2 para-chloroacetophenone 
• 132531-89-6 2-(4-chlorophenyl)-1-(phenylsulfenyl)-1,2-bis(trifluoroacetoxy)ethane 
• 53896-48-3 2-iodo-4'-chloroacetophenone 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 39561-82-5 4-chlorophenacyl acetate 
• 2788-86-5 4-Chlorostyrene oxide 
• 872182-24-6 2-(tert-butyl-dimethyl-silanyloxy)-1-(4-chloro-phenyl)-ethanol 
• 7477-64-7 1-(p-chlorophenyl)-1,2-ethanediol 
• 518068-75-2 2,4-dinitro-benzenesulfonic acid 2-(4-chloro-phenyl)-2-oxo-ethyl ester 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 937-20-2 p-chlorophenacyl chloride 

Downstream Products

• 35730-25-7 1-(4-bromo-phenyl)-1-(4-chloro-phenyl)-ethane-1,2-diol 
• 57068-74-3 N-butyl-N-[4-(4-chloro-phenyl)-oxazol-2-yl]-isobutyramide 
• 61883-64-5 butyl-[4-(4-chloro-phenyl)-oxazol-2-yl]-amine 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 123365-20-8 1-(4-Chloro-phenyl)-2-methoxymethoxy-ethanone 
• 74-11-3 para-chlorobenzoic acid 
• 50-00-0 formaldehyd 
• 244031-71-8 1-(4-chlorophenyl)-2-[(tetrahydro-2H-pyran-2-yl)-oxy]-ethan-1-one 
• 7477-64-7 (S)-1-(4-chlorophenyl)-1,2-ethanediol 
• 399040-13-2 2-amino-4-(4-chlorophenyl)furan-3-carbonitrile 
• 871024-63-4 1-(4-chlorophenyl)-2-hydroxy-3-(N-diphenylphosphinoylamino)-3-phenylpropan-1-one 
• 217650-32-3 N-[1-(4-chloro-phenyl)-2-methoxymethoxy-vinyl]-acetamide 

Relevant academic research and scientific papers

DIRECT α-HYDROXYLATION OF KETONES USING IODOSOBENZENE

Ketones are converted smoothly into the corresponding acyloin with a high degree of selectivity upon treatment with iodosobenzene or phenyl-iodosodiacetate in methanolic sodium hydroxyde.

A mild and efficient biomimetic synthesis of α-hydroxymethylarylketones from oxiranes in the presence of β-cyclodextrin and NBS in water

α-Hydroxymethylarylketones can be synthesized in good yields from easily accessible epoxides in the presence of β-cyclodextrin and NBS in water. This method is a direct, one-pot, synthesis under mild conditions using water as solvent and has many advantages over existing methodologies.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides

In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

Copper-catalyzed selective oxidation of hydrazones through C(sp3)-H functionalization

A simple and mild protocol for copper-catalyzed oxidation of hydrazones at the α-position has been reported. Various substrates are compatible, providing the corresponding products in moderate to good yields. This strategy provides an efficient and convenient solution for the synthesis of carbonyl hydrazone. A free radical pathway mechanism is suggested for the transformation.

Aerobic Direct Dioxygenation of Terminal/Internal Alkynes to α-Hydroxyketones by an Fe Porphyrin Catalyst

We herein report a new synthetic method for the preparation of α-hydroxyketones by the dioxygenation of alkynes. The reaction proceeds at room temperature under the action of Fe porphyrin and pinacolborane under air as a green oxidant to produce α-hydroxyketones. The mild reaction conditions allow chemoselective oxidation with functional group tolerance. Terminal alkynes in addition to internal alkynes are applicable, affording unsymmetrical α-hydroxyketones that are difficult to obtain by any reported dioxygenation of unsaturated C?C bonds.

One-Pot Enzymatic-Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones

2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.

Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase

Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.