78038-42-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(4-NITROPHENYL)OXIRANE is used as a reagent in the enantioconvergent synthesis of the β-blocker (R)-Nifenalol. This synthesis is based on a combined chemoenzymic approach, which allows for the selective production of the desired enantiomer with high efficiency and selectivity. The use of (S)-2-(4-NITROPHENYL)OXIRANE in this process is crucial for obtaining the desired chiral center in the final product, which is essential for the biological activity and therapeutic effects of the β-blocker.
In addition to its application in the synthesis of (R)-Nifenalol, (S)-2-(4-NITROPHENYL)OXIRANE can also be used as a reagent in the synthesis of other chiral compounds with potential pharmaceutical applications. Its unique reactivity and selectivity make it a valuable tool for chemists working on the development of new drugs and therapeutic agents.
Furthermore, (S)-2-(4-NITROPHENYL)OXIRANE can be employed in other industries that require the synthesis of chiral compounds, such as the agrochemical, fragrance, and flavor industries. Its ability to provide enantioselective synthesis routes can help in the development of more effective and environmentally friendly products in these fields.

InChI:InChI=1/C8H7NO3/c10-9(11)7-3-1-6(2-4-7)8-5-12-8/h1-4,8H,5H2/t8-/m1/s1

Upstream product

• 100-13-0 4-nitrostyrene 
• 125653-67-0 (R)-(-)-2-bromo-1-(4-nitrophenyl)ethanol 
• 325856-49-3 (R)-2-chloro-1-(4-nitrophenyl)ethanol 
• 19922-82-8 2-bromo-1-(4-nitrophenyl)ethanol 
• 502934-29-4 (R)-1-(4-nitrophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 6388-74-5 p-Nitrophenyloxirane 
• 99-81-0 4-Nitrophenacyl bromide 
• 13407-16-4 α-(chloromethyl)-4-nitrobenzyl alcohol 
• 536-74-3 phenylacetylene 
• 623-47-2 propynoic acid ethyl ester 
• 216160-44-0 (S)-2-chloro-1-(4-nitrophenyl)ethanol 
• 166239-06-1 (S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol 
• 77977-74-3 (S)-(+)-1-(4-nitrophenyl)-1,2-ethanediol 
• 34006-49-0 2-chloro-1-(4-nitrophenyl)ethanone 

Downstream Products

• 5054-57-9 (-)-Nifenalol 
• 77977-74-3 (S)-(+)-1-(4-nitrophenyl)-1,2-ethanediol 
• 77977-74-3 (R)-(-)-1-(4-nitrophenyl)-1,2-ethanediol 
• 325856-49-3 (R)-2-chloro-1-(4-nitrophenyl)ethanol 
• 166239-06-1 (S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol 
• 1304788-12-2 C₁₄H₁₃NO₄ 
• 1312566-14-5 (S)-3-(2-hydroxy-2-(4-nitrophenyl)ethylamino)propan-1-ol 
• 1312564-98-9 (S)-N-(4-(1,4-oxazepan-2-yl)phenyl)-3-chlorobenzamide hydrochloride 
• 1312566-16-7 (S)-tert-butyl (2-hydroxy-2-(4-nitrophenyl)ethyl)(3-hydroxypropyl)carbamate 
• 1312566-17-8 (S)-tert-butyl 2-(4-nitrophenyl)-1,4-oxazepane-4-carboxylate 
• 1312566-18-9 (S)-tert-butyl 2-(4-aminophenyl)-1,4-oxazepane-4-carboxylate 
• 1312566-19-0 (S)-tert-butyl 2-(4-(3-chlorobenzamido)phenyl)-1,4-oxazepane-4-carboxylate 
• 5302-36-3 (+)-Nifenalol 
• 397869-61-3 (S)-2-azido-1-(4-nitrophenyl)ethan-1-ol 

Relevant academic research and scientific papers

Biomimetic non-heme iron-catalyzed epoxidation of challenging terminal alkenes using aqueous H2O2 as an environmentally friendly oxidant

Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations.

Preparing β-blocker (R)-Nifenalol based on enantioconvergent synthesis of (R)-p-nitrophenylglycols in continuous packed bed reactor with epoxide hydrolase

An engineered epoxide hydrolase from Vigna radiate (VrEH2M263N) shows near-perfect enantioconvergence in single enzyme mediated hydrolysis of racemic p-nitrostyrene oxide (pNSO). To explore industrial potential of the promising biocatalyst, we tried to immobilize the VrEH2 variant by covalently linking onto a commercially available amino resin ECR8405F. Then a 5-mL packed bed reactor filled with the immobilized VrEH2M263N was connected with macroporous resin NKA-11 for in situ product adsorption, and the product (R)-p-nitrophenyl glycol (pNPG) was harvested by methanol elution, with 91% isolated yield and 97% ee. The continuous reactor was operated stably for more than 100 h with a space time yield of 20 g?L?1?h?1. Subsequently, the β-blocker (R)-Nifenalol was prepared by chemically synthesized from (R)-pNPG, affording the product in an overall yield of 61.3% (1.5 g) and an enantiopurity of 99.9% ee after recrystallization.

Multistep Organic Transformations over Base-Rhodium/Diamine-Bifunctionalized Mesostructured Silica Nanoparticles

The assembly of multiple catalytic functionalities within a single mesoporous silica as a catalyst for multistep enantioselective organic transformations in an environmentally friendly medium is a significant challenge in heterogeneous asymmetric catalysis. Herein, we took advantage of a BF4 ? anion hydrogen bonding strategy to anchor a chiral cationic rhodium/diamine complex within base-functionalized mesostructured silica nanoparticles conveniently to construct a bifunctional heterogeneous catalyst. The solid-state 13C NMR spectrum discloses the well-defined chiral Rh/diamine active species, and we used XRD, N2 adsorption–desorption, and electron microscopy to reveal the ordered mesostructure. The combination of bifunctionality in the silica nanoparticles enables two kinds of efficient enantioselective organic transformations with high yields and enantioselectivities, in which the asymmetric transfer hydrogenation of α-haloketones followed by epoxidation provides various chiral aryloxiranes, and the amination of α-haloketones with anilines followed by asymmetric transfer hydrogenation produces various β-amino alcohols. Furthermore, the catalyst can be recovered and recycled for seven times without a loss of catalytic activity, which is an attractive feature for multistep organic transformations in a sustainable benign process.

Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water

A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ring-opening of enantiopure styryl and pyridyl (S)-epoxides by N3- in hot water takes place preferentially at the internal position with complete inversion of configuration to produce (R)-2-azido ethanols with up to 99% enantio- and regioselectivity, while the (S)-adamantyl oxirane provides mainly the (S)-1-adamantyl-2-azido ethanol in excellent yield. In general, 1,2-amino ethanols were obtained in high yield and excellent enantiopurity by the reduction of the chiral 1,2-azido ethanols with PPh3 in water/THF, and then converted into the Boc or acetamide derivatives.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Asymmetric epoxidation of alkenes and benzylic hydroxylation with P450tol monooxygenase from Rhodococcus coprophilus TC-2

P450tol monooxygenase was discovered as a unique and highly enantioselective enzyme for asymmetric epoxidation of some terminal alkenes containing electron-withdrawing groups and benzylic hydroxylation of several ethylbenzenes giving the corresponding useful and valuable products, such as (R)-2- and 3-substituted styrene oxides, (S)-4-substituted styrene oxides, and (S)-benzylic alcohols, in high ee.

One-pot route to β-adrenergic blockers via enantioselective organocatalysed epoxidation of terminal alkenes as a key step

A convenient and environmentally attractive one-pot two-step process for the synthesis of β-adrenergic blockers via Shi's organocatalytic epoxidation of terminal alkenes and subsequent aminolysis reaction of epoxides with isopropylamine under mild reaction conditions has been developed. This journal is the Partner Organisations 2014.

Engineered P450pyr monooxygenase for asymmetric epoxidation of alkenes with unique and high enantioselectivity

A triple mutant of P450pyr monooxygenase (P450pyrTM) catalysed the epoxidation of several para-substituted styrenes as the first enzyme showing high (R)-enantioselectivity and high conversion, demonstrated a broad substrate range, and showed high enantioselectivity for the epoxidation of an unconjugated 1,1-disubstituted alkene, 2-methyl-3-phenyl-1-propene, and a cyclic alkene, N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine, respectively.

Stereoselective epoxidation of alkenes with hydrogen peroxide using a bipyrrolidine-based family of manganese complexes

Novel manganese complexes containing N4-tetradentate ligands derived from chiral bipyrrolidinediamines catalyze the stereoselective epoxidation of a wide array of alkenes using low catalyst loadings (0.1 mol%) and hydrogen peroxide (1.2 equiv.) as terminal oxidant. This family of catalysts affords good to excellent yields (80-100%) and moderate to good ees (40-73%) in short reaction times (30 min) making efficient use of hydrogen peroxide.

Asymmetric synthesis of β-adrenergic blockers through multistep one-pot transformations involving in situ chiral organocatalyst formation

Two birds one stone: A new atom-economical one-pot approach to enantioselective chiral drug synthesis, involving in situ multistep organocatalyst formation and the application of the reaction for multistep sequential synthesis of β-adrenergic blockers is disclosed (see scheme).