54458-61-6 Usage
Description
2,3,4,5-Tetramethyl-2-cyclopentenone is an organic compound characterized by its unique molecular structure, featuring a cyclopentenone ring with four methyl groups attached at various positions. 2,3,4,5-Tetramethyl-2-cyclopentenone is known for its potential applications in the fields of organic synthesis and pharmaceuticals, making it a valuable compound for research and development.
Uses
Used in Organic Synthesis:
2,3,4,5-Tetramethyl-2-cyclopentenone is used as an organic synthesis intermediate for the creation of various complex organic molecules. Its unique structure allows for a wide range of reactions, making it a versatile building block in the synthesis of numerous compounds.
Used in Pharmaceutical Intermediates:
In the pharmaceutical industry, 2,3,4,5-Tetramethyl-2-cyclopentenone serves as a key intermediate in the development of new drugs. Its reactivity and structural properties make it a valuable component in the synthesis of various pharmaceutical compounds.
Used in Laboratory Research and Development:
2,3,4,5-Tetramethyl-2-cyclopentenone is extensively utilized in laboratory settings for research and development purposes. Its unique properties and reactivity make it an essential tool for scientists working on the synthesis of new organic compounds and pharmaceuticals.
Used in Chemical Production Processes:
2,3,4,5-Tetramethyl-2-cyclopentenone is also used in the chemical production process, where it plays a crucial role in the synthesis of various chemicals and materials. Its versatility and reactivity contribute to the efficiency and effectiveness of these production processes.
Used in the Synthesis of Chiral Pre-ligands:
2,3,4,5-Tetramethyl-2-cyclopentenone has been employed in the synthesis of chiral pre-ligands, such as (R)-3,3'-bis(tetramethylcyclopentadienyl)-2,2'-bismethoxy-1,1'-bisnaphthalene and (R)-3-tetramethylcyclopentadienyl-2,2'-bismethoxy-1,1'-bisnaphthalene. These pre-ligands are obtained by reacting the compound with (R)-3,3'-dilithium-2,2'-bismethoxy-1,1'-bisnaphthalene, showcasing its importance in the development of chiral compounds with potential applications in various fields.
Synthesis
In a bottom round flask equipped with a mechanical stirrer, a dropping funnel and a reflux condenser was loaded 2000g (23.2 mol) of the starting ketone with 75% w/w of butylacetate as the solvent, 0.35 molar equivalents of anhydrous magnesium chloride and the aforementioned titanium catalytic solution containing 0.06 molar equivalents of the trichloropropoxytitanium complex. The resulting suspension was stirred vigorously and allowed to heat to 90°C. Then 2 molar equivalents of the acetaldehyde were added dropwise over 3h at 90°C. The reaction was continued for an additional hour and cooled to 40°C. The reaction mixture was hydrolysed with a 10% aqueous acetic acid solution and neutralised with a 20% aqueous potassium carbonate solution. The resulting organic phase was directly fractionated into a laboratory Sulzer packed column, to afford the title compound, as a mixture of isomers trans:cis = 85:15, in 27 % yield and the enone (II) (i.e. 4-methyl-4-hexen-3-one) in 31 % yield. mixture of isomers trans:cis = (B.p. = 70-80°C at P = 8 mbar); 4-methyl-4-hexen-3-one = (B.p. = 45-65°C at P = 8 mbar). 1H-NMR (isomer trans): 1.15 (d 3H); 1.19 (d 3H); 1.68 (s 3H); 1.88 (m 1H); 1.98 (s 3H); 2.25 (m 1H). 13C-NMR (isomer trans): 8.5; 14.6; 15.1 ; 17.7; 46.2; 48.4; 134.5; 171.6; 21 1.0.
Check Digit Verification of cas no
The CAS Registry Mumber 54458-61-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,4,5 and 8 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 54458-61:
(7*5)+(6*4)+(5*4)+(4*5)+(3*8)+(2*6)+(1*1)=136
136 % 10 = 6
So 54458-61-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O/c1-5-6(2)8(4)9(10)7(5)3/h5,7H,1-4H3/t5-,7-/m0/s1
54458-61-6Relevant articles and documents
Photocatalytic degradation of water taste and odour compounds in the presence of polyoxometalates and TiO2: Intermediates and degradation pathways
Fotiou, Theodora,Triantis, Theodoros M.,Kaloudis, Triantafyllos,Papaconstantinou, Elias,Hiskia, Anastasia
, p. 1 - 9 (2014/05/20)
Geosmin (GSM) and 2-methylisoborneol (MIB) are produced by several species of cyanobacteria and actinomycetes. These compounds can taint water and fish causing undesirable taste and odours. Studies have shown that GSM/MIB are resistant in standard water treatments. Polyoxometalates (POM) are efficient photocatalysts in the degradation and mineralization of a great variety of organic pollutants, presenting similar behaviour with the widely published titanium dioxide (TiO2). Photocatalytic degradation of GSM and MIB under UV-A light in the presence of a characteristic POM photocatalyst, SiW 12O404-, in aqueous solution has been studied and compared with the photodegradation by TiO2 suspensions. GSM and MIB are effectively degraded in the presence of both photocatalysts. Addition of OH radical scavengers (KBr and tertiary butyl alcohol, TBA) retards the photodegradation rates of both compounds, suggesting that photodegradation mechanism takes place via OH radicals. Intermediates identified using GC-MS in the case of GSM and MIB, are mainly identical in the presence of both photocatalysts, also suggesting a common reaction mechanism. Possible photocatalytic degradation pathway for both GSM and MIB is proposed.
Direct Synthesis of Polysubstituted Cyclopentenones from Ketones and Aldehydes Catalyzed by Zirconium Compounds
Yuki, Tsuyoshi,Hashimoto, Motochika,Nishiyama, Yutaka,Ishii, Yasutaka
, p. 4497 - 4499 (2007/10/02)
-
Convenient preparations of 1,2,3,4,5- pentamethylcyclopentadiene and 1-ethyl-2,3,4,5-tetramethylcyclopentadiene
Feitler, David,Whitesides, George M.
, p. 466 - 469 (2007/10/05)
-
