101001-06-3

Basic information

• Product Name: 3-[(E)-(4-NITROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE
• Synonyms: 3-[(E)-(4-NITROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE
• CAS NO: 101001-06-3
• Molecular Formula: C₁₆H₁₁NO₄
• Molecular Weight: 281.26
• Mol File: 101001-06-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-[(E)-(4-NITROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(E)-(4-NITROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE(101001-06-3)
• EPA Substance Registry System: 3-[(E)-(4-NITROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE(101001-06-3)

Safety Data

• Hazardous Substances Data: 101001-06-3(Hazardous Substances Data)

Upstream product

• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 79530-06-6 3-(4-nitro-benzyl)-chromen-4-one 
• 93362-72-2 3,4-Dihydro-3-isopropyl-2-(4-methylpiperazino)-4-(4-nitrophenyl)-2H,5H-pyrano<3,2-c>chromen 
• 1262616-66-9 (2'S,3S,4'R)-4'-hydroxy-2'-(4-nitrophenyl)spiro[chroman-3,3'-thiochroman]-4-one 
• 1262801-68-2 (S)-2-amino-4-(4-nitrophenyl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile 

Relevant articles and documents

Etude RMN(1)H et radiocristallographique de la stereochemie de 3-aryl-9b-hydroxy-1,3,3a,9b-tetrahydro-4H-thienobenzopyrane-1-carboxylates d'ethyle. Configuration et conformation

The reaction of ethyl mercaptoacetate with some 3-arylidene-4-chromanones yields the corresponding ethyl 3-aryl-9b-hydroxy-1,3,3a,9b-tetrahydro-4H-thienobenzopyrane-1-carboxylates.In spite of the presence of four chirality centers, the reaction is diastereospecific and gives a single diastereoisomer whose configuration and conformation were specified by its PMR data.The cis-fused tetrahydrothiophenic and dihydropyranic cycles lie in half-chair conformation.The 9b-hydroxyl and the 3-aryl groups are in a cis equatorial and pseudoequatorial disposition.The ester group, also cis with the hydroxyl group, presents a hydrogen bond with the hydroxyl.In the presence of an ortho-substituent at the phenyl group (particularly a chlorine atom), this phenyl group undergoes a notable rotation as is pointed out by a radiocristallographic study.A comparative study between the NMR and radiogcristallographic data allows the confirmation of the maintenance of the same conformation in solid and dissolved states.

Imidazolium ionic liquids as catalyst for synthesis of (E)-3- arylidene(thio)chroman-4-ones under microwave irradiation

Use of imidazolium ionic liquids [Bmim][CF3COO] and [Bmim]OH as a catalyst for synthesis of 3-arylidene(thio)chroman- 4-ones by the condensation of (thio)chroman-4-ones and aromatic aldehydes under microwave irradiation conditions. A series of 3-arylidene(thio)chroman-4-ones were obtained as the only product and considerable increase of yield was founded within short time. The products 3-arylidene(thio)chromanones were assigned the (E)-configuration based on 1H NMR spectroscopic data.

Novel synthesis of N-methyl spiropyrrolidines by 1,3-dipolar cycloaddition reaction of azomethine ylides

A series of novel N-methyl spiropyrrolidines have been synthesized in good yield by the cycloaddition reaction of azomethine ylides generated by a decarboxylative route from sarcosine and paraformaldehyde with conformationally locked s-trans enone functionality present in the (E)-3-arylidene-4-chromanone as dipolarophiles. The structure of the title compound was established by spectroscopic techniques. Copyright Taylor & Francis, Inc.