1569-94-4

Basic information

• Product Name: 5-Isoxazolemethanol, 4,5-dihydro-3-phenyl-
• CAS NO: 1569-94-4
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Mol File: 1569-94-4.mol

Chemical Properties

• CAS DataBase Reference: 5-Isoxazolemethanol, 4,5-dihydro-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isoxazolemethanol, 4,5-dihydro-3-phenyl-(1569-94-4)
• EPA Substance Registry System: 5-Isoxazolemethanol, 4,5-dihydro-3-phenyl-(1569-94-4)

Safety Data

• Hazardous Substances Data: 1569-94-4(Hazardous Substances Data)

Upstream product

• 873-67-6 benzonitrile oxide 
• 107-18-6 allyl alcohol 
• 932-90-1 syn-benzaldehyde oxime 
• 68843-67-4 (E)-1-phenylbut-3-en-1-one oxime 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 932-90-1 Benzaldoxime 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 68843-67-4 1-phenyl-but-3-en-1-one oxime 
• 100-52-7 benzaldehyde 
• 288404-17-1 (3-phenyl-4,5-dihydro-isoxazol-5-yl)-methanediol 
• 107-02-8 acrolein 
• 17647-39-1 3-phenyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester 
• 145732-24-7 3-Phenyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-ylmethyl)-4,5-dihydro-isoxazole 

Downstream Products

• 62353-37-1 5-(chloromethyl)-3-phenyl-4,5-dihydro-1,2-oxazole 
• 64984-98-1 4-phenyl-2-oxa-3-aza-bicyclo[3.1.0]hex-3-ene 
• 1338732-73-2 5-(N,N-dimethylaminomethyl)-3-phenyl-4,5-dihydroisoxazole 
• 138587-91-4 syn-3,4-dihydroxy-1-phenylhexan-1-one 
• 138587-91-4 anti-3,4-dihydroxy-1-phenylhexan-1-one 
• 86542-14-5 3-Hydroxy-1-phenyl-4-(tetrahydro-pyran-2-yloxy)-butan-1-one 
• 86542-13-4 4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-phenyl-butan-1-one 
• 159974-70-6 (2R,4R)-4-phenyl-1,2,4-butanetriol 
• 159974-69-3 (2S,4R)-4-phenyl-1,2,4-butanetriol 
• 159974-68-2 (R)-3,4-dihydroxy-1-phenylbutan-1-one 
• 159974-67-1 (S)-3,4-dihydroxy-1-phenylbutan-1-one 
• 124154-34-3 (S)-5-(Hydroxymethyl)-Δ²-isoxazoline 
• 119897-89-1 (R)-3-phenyl-Δ²-isoxazoline-5-methanol 

Relevant articles and documents

Preparation and 1-Carbon Homologation of Boronic Ester Substituted Δ2-isoxazolines: The 1,3 Dipolar Cycloaddition of Nitrile Oxides to Vinyl Boronic Esters

The dipolar cycloaddition of a variety of nitrile oxides to pinacol vinylboronate (2) is described.In addition, the 1-carbon homologation of the boronic ester substituted Δ2-isoxazolines obtained from the cycloadditions has been carried out emp

A Highly Effective Quenching Method of 1,3-Dipolar Cycloadditions of Nitrile Oxides or Nitrile Oxide/Lewis Acid Complexes by Use of 2-Propenyloxymagnesium Bromide

2-Propenyloxymagnesium bromide, readily prepared by treating 2-propen-1-ol with EtMgBr, is a highly effective quencher of nitrile oxide cycloadditions since this alkoxide is much more reactive to nitrile oxides than any other ever known dipolarophiles of

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Room temperature iron(ii)-catalyzed radical cyclization of unsaturated oximes with hypervalent iodine reagents

Here, we disclose an iron(ii)-catalyzed I-O bond cleavage of Koser's hypervalent iodine reagents (HIRs) that initiated the radical cyclization of unsaturated oximes at room temperature. This strategy is successfully applied for the construction of the isoxazoline backbone in an efficient manner. In particular, the direct introduction of a TsO group into products facilitates their late-stage transformations in organic synthesis.

Green organocatalytic synthesis of isoxazolines via a one-pot oxidation of allyloximes

A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in moderate to excellent yields.

Manganese-Promoted Oxidative Cyclization of Unsaturated Oximes Using Molecular Oxygen in Air under Ambient Conditions

A highly efficient manganese-promoted oxidative cyclization of unsaturated oximes to afford the corresponding 4,5-dihydroisoxazoline alcohols was developed. A very low loading (generally 0.1–0.2 mol-%) of Mn(acac)3(acac = acetylacetonate) promoted the oxidative cyclization through the direct incorporation of molecular oxygen present in air (open flask) at room temperature.

Organophotocatalytic Generation of N- and O-Centred Radicals Enables Aerobic Oxyamination and Dioxygenation of Alkenes

A cooperative TEMPO and photoredox catalytic strategy was applied for the first time to the direct conversion of N?H and O?H bonds into N- and O-centred radicals, enabling a general and selective oxidative radical oxyamination and dioxygenation of various

Metal-Free Autoxidative Nitrooxylation of Alkenyl Oximes with Molecular Oxygen

A metal-free aerobic autoxidative nitrooxylation of alkenyl oximes mediated by tert-butyl nitrite is described. Molecular oxygen is used as the oxidizing reagent, avoiding use of organic trapping reagents such as 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMP

METHOD FOR PRODUCING 4,5-DIHYDROISOXAZOLE

PROBLEM TO BE SOLVED: To provide a method for producing 4,5-dihydroisoxazole derivatives useful as pharmaceutical and agrochemical intermediates at low production costs and under mild reaction conditions. SOLUTION: The present invention provides a method for producing a compound represented by formula (I) or formula (II), comprising a cyclization step of making a compound represented by formula (III) or formula (IV) react with oxygen in the air in the presence of a catalyst comprising manganese to obtain a cyclized product. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Hypervalent iodine-catalyzed cycloaddition of nitrile oxides to alkenes

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was fi