Ethyl 2-methyl-4,4-diphenylbuta-2,3-dienoate

Base Information

• Chemical Name: Ethyl 2-methyl-4,4-diphenylbuta-2,3-dienoate
• CAS No.: 5717-43-1
• Molecular Formula: C19H18O2
• Molecular Weight: 278.351
• ChEMBL ID: CHEMBL443611
• DSSTox Substance ID: DTXSID80550351
• Nikkaji Number: J747.208K
• Mol file: 5717-43-1.mol

Synonyms:CHEMBL443611;Ethyl 2-methyl-4,4-diphenylbuta-2,3-dienoate;5717-43-1;SCHEMBL8638044;DTXSID80550351;BDBM50292631;alpha-methyl-gamma,gamma-diphenylallenecarboxylic acid ethyl ester

Chemical Property of Ethyl 2-methyl-4,4-diphenylbuta-2,3-dienoate

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 278.130679813
• Heavy Atom Count: 21
• Complexity: 383

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=C=C(C1=CC=CC=C1)C2=CC=CC=C2)C

Technology Process of Ethyl 2-methyl-4,4-diphenylbuta-2,3-dienoate

There total 7 articles about Ethyl 2-methyl-4,4-diphenylbuta-2,3-dienoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

1-ethoxy-2-methyl-1-oxo-4-phenylbut-3-yn-2-yl 2-iodobenzoate + phenylboronic acid (98-80-6) → α-methyl-γ,γ-diphenylallenecarboxylic acid ethyl ester (5717-43-1) + ethyl 4-(diphenylmethylene)-3-methyl-1-oxoisochroman-3-carboxylate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 14h; Microwave irradiation; Inert atmosphere;

DOI:10.1021/jacs.6b00278

Reference yield: 59.0%

diphenylacetic acid chloride (1871-76-7) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → α-methyl-γ,γ-diphenylallenecarboxylic acid ethyl ester (5717-43-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1021/ja011428g

Reference yield: 38.0%

iron(III) chloride hexahydrate (121714-78-1,24290-40-2,58694-80-7,10025-77-1,64333-00-2) + hexacarbonyl(ethyl 2-methyl-4,4-diphenyl-2,3-butadienoate)diiron → ((C6H5)2CCC(CH3)COOC2H5)Fe(CO)4 (120438-57-5) + ((C6H5)2CCHC(CH2)COOC2H5)Fe(CO)3 (120438-56-4) + α-methyl-γ,γ-diphenylallenecarboxylic acid ethyl ester (5717-43-1)

Guidance literature:

In methanol; stirring, room temp., 24 h; the mixture of the two iron complexes (orange oil) was not amenable to chromatographic sepn.; evapn. (vac.), addn. of H2O, extn. (Et2O); evapn., TLC (petr. ether/Et2O 9:1), elution (CHCl3), evapn. (vac.), dissolving (petr. ether/Et2O 9:1), keeping at -15 °C (pptn. of the allene); evapn. to dryness in vac.; IR, MS, (1)H-NMR;

DOI:10.1002/hlca.19880710307

upstream raw materials:

diphenylacetic acid chloride

(carbethoxyethylidene)triphenylphosphorane

diphenyl ketene

iron(III) chloride hexahydrate

Downstream raw materials:

4-fluoro-3-methyl-5,5-diphenyl-2(5H)-furanone

3-(p-bromophenyl)-2-methyl-4-phenyl-1-naphthol

3-(p-fluorophenyl)-2-methyl-4-phenyl-1-naphthol

3,4-diphenyl-2-methyl-1-naphthol

Refernces

• 1、 Lue, Bo,Fu, Chunling,Ma, Shengming. "Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: An efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates". supporting information; experimental part. p. 274 - 281. Retrieved 2010/04/24.
• 2、 Trifonov, Latchezar S.,Orahovats, Alexander S.,Prewo, Roland,Heimgartner, Heinz. "Synthesis and Structure of Carbonyliron Complexes of Allenecarboxylates and Allenic Lactones". . p. 551 - 561. Retrieved 2007/10/02.