5007-50-1

Basic information

• Product Name: 1-FURAN-2-YL-ETHANONE OXIME
• Synonyms: ART-CHEM-BB B006531;AKOS B006531;1-(2-FURYL)ETHANONE OXIME;1-(2-FURYL)-1-ETHANONE OXIME;1-FURAN-2-YL-ETHANONE OXIME;(1Z)-1-(2-Furyl)ethanone oxime;(NZ)-N-(1-furan-2-ylethylidene)hydroxylamine;(Z)-1-(furan-2-yl)ethanone oxime
• CAS NO: 5007-50-1
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.13
• Mol File: 5007-50-1.mol

Chemical Properties

• Melting Point: 104 °C
• Boiling Point: 218.8 °C at 760 mmHg
• Flash Point: 86.1 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0.0716mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 1-FURAN-2-YL-ETHANONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FURAN-2-YL-ETHANONE OXIME(5007-50-1)
• EPA Substance Registry System: 1-FURAN-2-YL-ETHANONE OXIME(5007-50-1)

Safety Data

• Hazardous Substances Data: 5007-50-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Furan-2-yl-ethanone oxime is utilized as a reagent in organic synthesis, playing a crucial role in the formation of complex organic molecules. Its ability to participate in various chemical reactions makes it a valuable component in the synthesis of a wide range of organic compounds.
Used in Metal Complexation:
As a chelating agent, 1-Furan-2-yl-ethanone oxime is employed in metal complexation reactions. It forms stable complexes with metal ions, which is essential in various chemical processes and applications, including the development of catalysts and the study of metal ion behavior.
Used in Pharmaceutical Development:
1-Furan-2-yl-ethanone oxime has been studied for its potential as an anti-cancer agent, given its capacity to inhibit certain enzymes that play a role in cancer development and progression. This property positions it as a candidate for the development of new pharmaceuticals targeting cancer treatment.
Additionally, it has been investigated for its anti-inflammatory properties, which could lead to its use in the development of medications for inflammatory conditions.
Used in Agrochemical Production:
1-Furan-2-yl-ethanone oxime has also been explored for its use in the production of agrochemicals. Its potential applications in this field could include the development of pesticides or other compounds that enhance crop protection and yield.

InChI:InChI=1/C6H7NO2/c1-5(7-8)6-3-2-4-9-6/h2-4,8H,1H3/b7-5+

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 68727-98-0 N'-(1-(furan-2-yl)ethylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 99969-04-7 N-(furan-2-yl)acetamide 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 5689-65-6 2,6-di(furan-2-yl)-4-phenylpyridine 
• 63122-43-0 2-(2'-furanyl)pyrrole 
• 1198575-44-8 7-methyl-4,5-diphenylfuro[2,3-c]pyridine 
• 188772-55-6 (Z)-1-(furan-2-yl)ethanone O-benzyloxime 
• 132523-44-5 (R)-1-(furan-2-yl)ethanamine 

Relevant articles and documents

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides

We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.

Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations

A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.

Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones

A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3-amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3-dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.

Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions

A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.

High add valued application of turpentine in crop production through structural modification and qsar analysis

Turpentine is a volatile component of resin, which is an abundant forest resource in Southern China. As one of the most important components, the integrated application of-pinene has been studied. The broad-spectrum evaluation of -pinene and its analogues has, therefore, been necessary. In an attempt to expand the scope of agro-activity trials, the preparation and the evaluation of the herbicidal activity of a series of -pinene analogues against three agricultural herbs were carried out. In accordance with the overall herbicidal activity, it is noteworthy that compounds 6k, 6l, and 6m demonstrated extreme activity with IC50 values of 0.065, 0.065, and 0.052 mol active ingredients/hectare against E. crus-galli. The preliminary structure-activity relationship (SAR) was analyzed and the compounds with the appropriate volatility and substituent type that had beneficial herbicidal activity were analyzed. Simultaneously, the quantitative structure-activity relationship (QSAR) model was built and the most important structural features were indicated, which was, to a certain extent, in line with the SAR study. The study aimed to study the application of the forest resource turpentine in agriculture as a potential and alternative approach for comprehensive utilization.

Cu-Catalyzed Coupling of O-Acyl Oximes with Isatins: Domino Rearrangement Strategy for Direct Access to Quinoline-4-Carboxamides by C–N Bond Cleavage

A mild domino rearrangement strategy for the direct access to substituted quinoline-4-carboxamides has been developed. This copper-catalyzed coupling reaction of O-acyl oximes with isatins in the presence of molecular oxygen as the sole oxidizing agent proceeds through a ring expansion of the isatins through cleavage of the two C–N bonds.

Catalytic Enantio- and Diastereoselective Mannich Addition of TosMIC to Ketimines

Chiral amines bearing a stereocenter in the α position are ubiquitous compounds with many applications in the pharmaceutical and agrochemical sectors, as well as in catalysis. Catalytic asymmetric Mannich additions represent a valuable method to access such compounds in enantioenriched form. This work reports the first enantio- and diastereoselective addition of commercially available p-toluenesulfonylmethyl isocyanide (TosMIC) to ketimines, affording 2-imidazolines bearing two contiguous stereocenters, one of which is fully-substituted, with high yields and excellent stereocontrol. The reaction, catalyzed by silver oxide and a dihydroquinine-derived N,P-ligand, is broad in scope, operationally simple, and scalable. Derivatization of the products provides enantioenriched vicinal diamines, precursors to NHC ligands and sp3-rich heterocyclic scaffolds. Computations are used to understand catalysis and rationalize stereoselectivity.

Copper-catalyzed radical/radical cross-coupling of ketoxime carboxylates with 4-hydroxycoumarins: A novel synthesis of furo[3,2-c]-coumarins

A novel and efficient strategy for the synthesis of furo[3,2-c]coumarins has been developed via copper-catalyzed radical/radical cross-coupling of ketoxime carboxylates with 4-hydroxycoumarins. This redox-neutral reaction allows smooth and selective synthesis of 2-substituted, 3-substituted, 2,3-disubstituted and 2,3-fused polycyclic furo[3,2-c]coumarins.

Synthesis of enaminones via copper-catalyzed decarboxylative coupling reaction under redox-neutral conditions

A novel copper-catalyzed C(sp3)-H oxidative functionalization of aromatic oxime acetates with α-oxocarboxylic acids was reported. This process involved N-O/C-C bond cleavages and C-C bond formations to furnish substituted enaminones under redox-neutral conditions. The oxime acetates served as both reactants and internal oxidants. Furthermore, this transformation also features good functional group tolerance and needs no ligands or additional bases.