2-Cyclohexen-1-one, 3-phenyl-

Base Information

• Chemical Name: 2-Cyclohexen-1-one, 3-phenyl-
• CAS No.: 10345-87-6
• Molecular Formula: C12H12 O
• Molecular Weight: 172.227
• Hs Code.: 2914399090
• European Community (EC) Number: 233-755-1
• NSC Number: 63067
• UNII: WRW3EDX5ZE
• DSSTox Substance ID: DTXSID2065044
• Nikkaji Number: J81.496B
• Wikidata: Q72501562
• ChEMBL ID: CHEMBL503170
• Mol file: 10345-87-6.mol

Synonyms:10345-87-6;3-Phenylcyclohex-2-en-1-one;3-Phenyl-2-cyclohexen-1-one;2-Cyclohexen-1-one, 3-phenyl-;3-Phenyl-2-cyclohexenone;5,6-Dihydro[1,1'-biphenyl]-3(4H)-one;1-Phenylcyclohexen-3-one;5,6-Dihydro-[1,1'-biphenyl]-3(4H)-one;3-phenylcyclohex-2-enone;CHEMBL503170;EINECS 233-755-1;NSC 63067;NSC-63067;SMR000477876;NSC63067;WRW3EDX5ZE;3-Phenyl-cyclohex-2-enone;NCIOpen2_000257;MLS001060693;MLS001180171;SCHEMBL679561;3-phenyl-cyclohex-2-en-1-one;DTXSID2065044;3-Phenyl-2-cyclohexen-1-one #;HMS2201B09;HMS3354N13;BDBM50243787;AKOS006343762;NCGC00161071-01;NCGC00161071-02;BS-26175;EN300-85031;A851266;Z1201617608

Chemical Property of 2-Cyclohexen-1-one, 3-phenyl-

Chemical Property:

• Vapor Pressure: 0.00344mmHg at 25°C
• Melting Point: 64-65℃
• Boiling Point: 282°Cat760mmHg
• Flash Point: 113.7°C
• PSA: 17.07000
• Density: 1.087g/cm³
• LogP: 2.82300
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 172.088815002
• Heavy Atom Count: 13
• Complexity: 221

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Phenyl-2-cyclohexen-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=CC(=O)C1)C2=CC=CC=C2
• Uses: 3-Phenyl-2-cyclohexen-1-one is an intermediate used to prepare niacin receptor agonists for the treatment of dyslipidemia. It is also used in the synthesis of inhibitors for urinary bladder rhythmic contraction.

Technology Process of 2-Cyclohexen-1-one, 3-phenyl-

There total 140 articles about 2-Cyclohexen-1-one, 3-phenyl- 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: 100.0%

1-phenyl-2-cyclohex-2-en-1-ol (60174-90-5) → 3-phenylcyclohex-2-enone (10345-87-6)

Guidance literature:

With laccase from Trametes versicolor; oxygen; 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In dimethyl sulfoxide; at 30 ℃; for 24h; under 760.051 Torr; pH=5.2; Schlenk technique; Enzymatic reaction;

DOI:10.1002/adsc.201800299

Reference yield: 100.0%

3-Ethoxycyclohex-2-en-1-one (5323-87-5) + phenylmagnesium bromide (100-58-3) → 3-phenylcyclohex-2-enone (10345-87-6)

Guidance literature:

3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

With hydrogenchloride; water; In tetrahydrofuran;

Reference yield: 95.0%

1-Phenylcyclohexene (771-98-2) → 3-phenylcyclohex-2-enone (10345-87-6)

Guidance literature:

With 2,6-dimethylpyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In water; acetonitrile; Electrolysis;

DOI:10.1016/j.tetlet.2005.02.032

upstream raw materials:

1-phenyl-3-(piperidin-1-yl)propan-1-one

ethyl acetoacetate

1-phenylcyclohexanol

1-phenyl-1-cyclohexane

Downstream raw materials:

3-methylbiphenyl

m-sexiphenyl

1,3-diphenyl-cyclohexa-1,3-diene

(rac)-3-phenyl-3-methylcyclohexanone

Refernces

• 1、 Gottumukkala, Aditya L.,Teichert, Johannes F.,Heijnen, Dorus,Eisink, Niek,Van Dijk, Simon,Ferrer, Catalina,Van Den Hoogenband, Adri,Minnaard, Adriaan J.. "Pd-diimine: A highly selective catalyst system for the base-free oxidative heck reaction". . p. 3498 - 3501. Retrieved 2011.
• 2、 Na, Sung Jae,Lee, Bun Yeoul,Bui, Nhat-Nguyen,Mho, Sun-il,Jang, Hye-Young. "A new dirhodium tetraacetate carbenoid: Synthesis, crystal structure and catalytic application". . p. 5523 - 5527. Retrieved 2007.
• 3、 Ozaki, Yutaka,Kubo, Ayako,Kim, Sang-Won. "A Method for the Cyclic Enone Synthesis Using Lithium Chloride-Hexamethylphosphoramide System". . p. 993 - 994. Retrieved 1993.
• 4、 Li, Yuancheng,Lee, Tae Bum,Wang, Tanyu,Gamble, Audrey V.,Gorden, Anne E. V.. "Allylic C-H activations using Cu(II) 2-quinoxalinol salen and tert-butyl hydroperoxide". . p. 4628 - 4633. Retrieved 2012.
• 5、 Kamijo, Shin,Dudley, Gregory B.. "Tandem nucleophilic addition/fragmentation reactions and synthetic versatility of vinylogous acyl triflates". . p. 6499 - 6507. Retrieved 2006.
• 6、 Guthrie,Guo. "Intramolecular aldol condensations: Rate and equilibrium constants". . p. 11472 - 11487. Retrieved 1996.
• 7、 Scheuermann Nee Taylor, Caroline J.,Jaekel, Christoph. "Enantioselective hydrogenation of enones with a hydroformylation catalyst". . p. 2708 - 2714. Retrieved 2008.
• 8、 Cho, Chan Sik,Motofusa, Shin-Ichi,Uemura, Sakae. "Antimony(III) chloride as an efficient catalyst for palladium-catalyzed hydrophenylation of α,β-unsaturated ketones and aldehydes". . p. 1739 - 1742. Retrieved 1994.
• 9、 Vatèle, Jean-Michel. "Lewis acid promoted oxidative rearrangement of tertiary allylic alcohols with the PhIO/TEMPO system". . p. 1785 - 1788. Retrieved 2008.
• 10、 Cho, Chan Sik,Motofusa, Shin-ichi,Ohe, Kouichi,Uemura, Sakae,Shim, Sang Chul. "A New Catalytic Activity of Antimony(III) Chloride in Palladium(0)-Catalyzed Conjugate Addition of Aromatics to α,β-Unsaturated Ketones and Aldehydes with Sodium Tetraphenylborate and Arylboronic Acids". . p. 883 - 888. Retrieved 1995.