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Cas Database

78589-68-1

78589-68-1

Identification

  • Product Name:methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

  • CAS Number: 78589-68-1

  • EINECS:

  • Molecular Weight:280.28

  • Molecular Formula: C17H12O4

  • HS Code:

  • Mol File:78589-68-1.mol

Synonyms:methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

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Relevant articles and documentsAll total 4 Articles be found

A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

Yoshida, Masahito,Saito, Koya,Fujino, Yuta,Doi, Takayuki

, p. 3452 - 3458 (2014/05/06)

A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c).

One-pot synthesis of 2-aryl-3-alkoxycarbonyl chromones through a cascade Lewis acid-catalyzed aldehyde olefination/oxa-Michael addition/oxidation

Wang, Ningning,Cai, Shuying,Zhou, Chao,Lu, Ping,Wang, Yanguang

, p. 647 - 652 (2013/07/25)

2-Aryl-3-alkoxycarbonyl chromones were effectively constructed from aryl aldehydes and 3-(2-(methoxymethoxy) phenyl)propiolates via a cascade Lewis acid catalyzed phenol ether deprotection/aldehyde olefination/intramolecular oxa-Michael addition reaction, and a sequential oxidation. This four-step reaction could be conducted in one-pot with high atom efficiency.

Alcohol mediated synthesis of 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives from 4-hydroxycoumarins

Zanwar, Manoj R.,Raihan, Mustafa J.,Gawande, Sachin D.,Kavala, Veerababurao,Janreddy, Donala,Kuo, Chun-Wei,Ambre, Ram,Yao, Ching-Fa

scheme or table, p. 6495 - 6504 (2012/10/08)

The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3- carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated.

NOUVEAU MODE DE CYCLYSATION DE CETO-YLURES. APPLICATION A UNE SYNTHESE IGINALE D'ACYL-3 HYDROXY-4-COUMARINES ET DE L'HYDROXY-11 BENZO-(b) 12 XANTHONE-12

Babin, P.,Dunogues, J.,Petraud, M.

, p. 1131 - 1139 (2007/10/02)

The thermal decomposition of keto-ylides resulting from the reaction of m- and p-acetoxy benzoyl chlorides with Ph3P=CH-COOMe leads, after saponification to m- and p-phenylpropiolic acid respectively.Ortho substitution by an acyl group generally changes the orientation of the reaction.Thus o-acetoxy-, benzoyloxy- or phenylacetoxy benzoyl chlorides respectively afford: and (R=Me,Ph) in satisfactory yields.Saponification of the first and second ones gives: (R=Me, Ph).This constitutes a new, convenient route to 3-acyl 4-hydroxy cumarins and 11-hydroxy 12H-benzoxanthene 12-one.Formation of these last products involves the carbonyl of the acyloxy-substituent and not of the acyl chloride as previously observed in these series.

Process route upstream and downstream products

Process route

methyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate
1607814-54-9

methyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
With 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; In toluene; at 30 ℃; for 25h; Solvent; Reagent/catalyst; Temperature; Catalytic behavior;
90%
1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one
16619-68-4

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2: 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine / toluene / 25 h / 30 °C
With 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; triethylamine; In dichloromethane; toluene;
methyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate
1607814-54-9

methyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
With tributylphosphine; In toluene; at 30 ℃; for 0.0833333h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;
97%
C<sub>17</sub>H<sub>14</sub>O<sub>4</sub>
1417564-38-5

C17H14O4

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 48h; Inert atmosphere; Reflux;
146 mg
4-hydroxy[1]benzopyran-2-one
1076-38-6,92395-12-5

4-hydroxy[1]benzopyran-2-one

nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
With triethylamine; In methanol; at 70 ℃; for 59h;
58%
methanol
67-56-1

methanol

C<sub>18</sub>H<sub>15</sub>NO<sub>4</sub>

C18H15NO4

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
With triethylamine; at 70 ℃; for 47h;
74%
methanol
67-56-1

methanol

nitrostyrene
5153-67-3

nitrostyrene

4-hydroxy[1]benzopyran-2-one
1076-38-6,92395-12-5

4-hydroxy[1]benzopyran-2-one

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
With triethylamine; at 70 - 80 ℃; for 49h;
72%
1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one
16619-68-4

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2: tributylphosphine / toluene / 0.08 h / 30 °C / Inert atmosphere
With tributylphosphine; triethylamine; In dichloromethane; toluene;
methyl 3-[2-(methoxymethoxy)phenyl]propiolate
1002130-71-3

methyl 3-[2-(methoxymethoxy)phenyl]propiolate

benzaldehyde
100-52-7

benzaldehyde

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 16 h / 50 °C / Inert atmosphere
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 48 h / Inert atmosphere; Reflux
With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; 1,2-dichloro-ethane;
benzaldehyde
100-52-7

benzaldehyde

methyl 3-(2-hydroxyphenyl)propiolate
425686-45-9

methyl 3-(2-hydroxyphenyl)propiolate

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
78589-68-1

methyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 12 h / 0 - 50 °C / Inert atmosphere
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 48 h / Inert atmosphere; Reflux
With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; 1,2-dichloro-ethane;

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