Norborn-5-en-2-yl phenyl ketone

Base Information

• Chemical Name: Norborn-5-en-2-yl phenyl ketone
• CAS No.: 6056-35-5
• Molecular Formula: C14H14O
• Molecular Weight: 198.265
• European Community (EC) Number: 227-983-0
• DSSTox Substance ID: DTXSID00975986
• Nikkaji Number: J227.271G
• Mol file: 6056-35-5.mol

Synonyms:6056-35-5;Norborn-5-en-2-yl phenyl ketone;2-Benzoyl-5-norbornene;bicyclo[2.2.1]hept-5-en-2-yl(phenyl)methanone;2-bicyclo[2.2.1]hept-5-enyl(phenyl)methanone;EINECS 227-983-0;{BICYCLO[2.2.1]HEPT-5-EN-2-YL}(PHENYL)METHANONE;5-Norbornene-2-benzoyl;Methanone, bicyclo(2.2.1)hept-5-en-2-ylphenyl-;Methanone, bicyclo[2.2.1]hept-5-en-2-ylphenyl-;(Bicyclo[2.2.1]hept-5-en-2-yl)(phenyl)methanone;2-Benzoylnorborna-5-ene;SCHEMBL818204;5-Norbornen-2-yl phenyl ketone;DTXSID00975986;AKOS015912925;AC-4857;2-Benzoyl-5-norbornene, exo(.+/-.);2-Benzoyl-5-norbornene, endo(.+/-.)

Chemical Property of Norborn-5-en-2-yl phenyl ketone

Chemical Property:

• Appearance/Colour: clear yellow-orange to brown liquid
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 296.881 °C at 760 mmHg
• Flash Point: 132.069 °C
• PSA: 17.07000
• Density: 1.13 g/cm³
• LogP: 3.08150
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 198.104465066
• Heavy Atom Count: 15
• Complexity: 286

Purity/Quality:

99%, ^*data from raw suppliers

2-Benzoyl-5-norbornene,mixture of endo and exo 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(C1C=C2)C(=O)C3=CC=CC=C3

Technology Process of Norborn-5-en-2-yl phenyl ketone

There total 11 articles about Norborn-5-en-2-yl phenyl ketone 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: 84.0%

(bicyclo[2.2.1]hept-5-en-2-yl)(pyrrolidin-1-yl)methanone + phenyllithium (591-51-5) → endo/exo-bicyclo[2.2.1]hept-5-en-2-yl(phenyl)methanone (6056-35-5)

Guidance literature:

In dibutyl ether; at 20 ℃; for 0.0166667h;

DOI:10.1002/chem.202004840

Reference yield: 78.0%

endo/exo-5-(1-phenylvinyl)bicilo[2.2.1]hept-2-ene → endo/exo-bicyclo[2.2.1]hept-5-en-2-yl(phenyl)methanone (6056-35-5)

Guidance literature:

With iron(III) trifluoromethanesulfonate; C₆₅H₇₇N₅O₄S₂; oxygen; In 1,2-dichloro-ethane; at 75 ℃; for 24h; under 760.051 Torr; chemoselective reaction; Green chemistry;

DOI:10.1021/jacs.5b03956

Reference yield: 72.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + Phenyl vinyl ketone (768-03-6,26742-84-7) → endo/exo-bicyclo[2.2.1]hept-5-en-2-yl(phenyl)methanone (6056-35-5)

Guidance literature:

With aluminium tris(2,6-diphenylphenoxide); In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ja00105a087

upstream raw materials:

bicyclo[2.2.1]hept-5-en-2-yl(phenyl)methanol

cyclopenta-1,3-diene

Phenyl vinyl ketone

phenyllithium

Downstream raw materials:

norborn-5-en-2-yl-phenyl-[2]pyridyl-methanol

exo-2-Brom-endo-2-benzoylbicyclo<2.2.1>heptan

(+/-)-phenyl-(norbornen-⁽⁵⁾-yl-(2endo))-ketone semicarbazone

(+/-)-[2endo]norbornyl-phenyl ketone

Refernces

• 1、 Ghinato, Simone,Territo, Davide,Maranzana, Andrea,Capriati, Vito,Blangetti, Marco,Prandi, Cristina. "A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects". supporting information. p. 2868 - 2874. Retrieved 2021/01/21.
• 2、 Bartley, David W.,Kodadek, Thomas J.. "CATALYSIS OF DIELS-ALDER REACTIONS BY METALLOPORPHYRINS". . p. 6303 - 6306. Retrieved 2007/10/02.