1171117-75-1

Basic information

• Product Name: (+)-(S)-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• Synonyms: (+)-(S)-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• CAS NO: 1171117-75-1
• Molecular Weight: 225.247
• Mol File: 1171117-75-1.mol

Chemical Properties

• CAS DataBase Reference: (+)-(S)-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one(1171117-75-1)
• EPA Substance Registry System: (+)-(S)-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one(1171117-75-1)

Safety Data

• Hazardous Substances Data: 1171117-75-1(Hazardous Substances Data)

Upstream product

• 27990-57-4 3-phenyl-1,4-benzoxazin-2-one 
• 1192307-86-0 (2-methoxy-2-oxo-(S)-1-phenylethyl) α-bromophenylacetate 
• 46425-95-0 o-(benzylamino)phenol 
• 902778-26-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromo-α-phenylacetate 
• 205748-19-2 (R,S)-2-Bromo-2-phenylacetic acid (R)-pantolactone ester 
• 95-55-6 2-amino-phenol 
• 129200-96-0 (2E)-3-phenyl-2-(phenylsulfonyl)-2-propenenitrile 
• 1417715-03-7 O,O'-di(α-bromo-α-phenylacetyl)-L-tartaric acid diisopropyl ester 
• 1327310-45-1 (2-ethoxy-(S)-1-methyl-2-oxoethyl) 2-bromo-2-phenylacetate 
• 1603-79-8 phenylglyoxylic acid ethyl ester 

Relevant articles and documents

Convenient asymmetric synthesis of both enantiomers of 3,4-disubstituted 3,4-dihydro-1,4-benzoxazin-2-ones

Both enantiomers of N-substituted 3-arylated 3,4-dihydro-1,4-benzoxazin-2-ones were conveniently synthesized up to 93:7 er based on the dynamic kinetic resolution of either (R)-pantolactone- or l-mandelate-derived α-bromo arylacetates in nucleophilic subs

Biomimetic reduction of imines and heteroaromatics with chiral and regenerable [2.2]Paracyclophane-Based NAD(P)H model CYNAM

In our previous work, we reported the synthesis of chiral and regenerable [2.2]paracyclophane-derived NAD(P)H models CYNAMs and their application in biomimetic asymmetric reduction of tetrasubstituted olefins. Herein, the biomimetic asymmetric reduction o

Catalytic Enantioselective Access to Dihydroquinoxalinones via Formal α-Halo Acyl Halide Synthon in One Pot

An enantioselective one-pot catalytic strategy to dihydroquinoxalinones, featuring novel 1-phenylsulfonyl-1-cyano enantioenriched epoxides as masked α-halo acyl halide synthons, followed by a domino ring-opening cyclization (DROC), is documented. A popula

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

Pnictogen-bonding catalysis based on σ-hole interactions has recently attracted the attention of synthetic chemists. As a proof-of-concept for asymmetric pnictogen-bonding catalysis, we report herein an enantioselective transfer hydrogenation of benzoxazi

Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]-Hydrogenase

[Fe]-hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]-hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development of a manganese(I) mimic of [Fe]-hydrogenase. This complex exhibits the highest activity and broadest scope in catalytic hydrogenation among known mimics. Thanks to its biomimetic nature, the complex exhibits unique activity in the hydrogenation of compounds analogous to methenyl-H4MPT+, the natural substrate of [Fe]-hydrogenase. This activity enables asymmetric relay hydrogenation of benzoxazinones and benzoxazines, involving the hydrogenation of a chiral hydride transfer agent using our catalyst coupled to Lewis acid-catalyzed hydride transfer from this agent to the substrates.

Exploration of chiral diastereomeric spiroketal (SPIROL)-based phosphinite ligands in asymmetric hydrogenation of heterocycles

New and readily available chiral SPIROL-based diphosphinite ligands (SPIRAPO) have been prepared and employed for iridium-catalyzed asymmetric hydrogenations of quinolines, quinoxalines and 2H-1,4-bezoxazin-2-ones. While the structurally similar (R,R,R)-SPIRAPO and (R)-SPINOL-based phosphinites were not the best ligands for these transformations, the (S,R,R)-diastereomer of SPIRAPO was found to be highly effective ligand for the reduction of 20 different heterocyclic systems with loadings as low as S/C = 10?000. This dearomatizative hydrogenation provided direct access to optically active tetrahydroquinolines in high enantioselectivities (up to 94percent ee) and excellent yields (up to 99percent), and was used to generate 1.75 g of natural alkaloid (-)-(R)-angustureine. This protocol was subsequently extended to achieve asymmetric hydrogenation of quinoxalines and 2H-1,4-benzoxazin-2-ones in good to excellent enantioselectivities.

Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts

Using ureas as transfer catalysts through hydrogen bonding activation, biomimetic asymmetric reduction of benzoxazinones and quinoxalinones with chiral and regenerable NAD(P)H models was described, giving chiral dihydrobenzoxazinones and dihydroquinoxalin

Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Br?nsted acid cocatalyst

The Ir-catalyzed highly efficient asymmetric hydrogenation of benzoxazinones and derivatives was successfully developed with N-methylated ZhaoPhos L5 as the ligand, which may display a new activation mode with a single anion-binding interaction among the

Relay iron/chiral bronsted acid catalysis: Enantioselective hydrogenation of benzoxazinones

An asymmetric hydrogenation reaction of benzoxazinones has been accomplished via a relay iron/chiral Bronsted acid catalysis. This approach provides a variety of chiral dihydrobenzoxazinones in good to high yields (75-96%) and enantioselectivities (up to