Pinocamphone

Base Information

• Chemical Name: Pinocamphone
• CAS No.: 547-60-4
• Deprecated CAS: 30517-87-4,1195518-93-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• European Community (EC) Number: 208-926-9,250-226-0
• UNII: 8W3PLY2V8K
• DSSTox Substance ID: DTXSID70881207
• Nikkaji Number: J215.932E
• Wikidata: Q27271103
• Metabolomics Workbench ID: 47201
• Mol file: 547-60-4.mol

Synonyms:isopinocamphon;pinocamphone;pinocamphone, (1alpha,2beta,5alpha)-isomer;pinocamphone, (1S-(1alpha,2beta,5alpha))-isomer

Chemical Property of Pinocamphone

Chemical Property:

• Boiling Point: 212°Cat760mmHg
• Flash Point: 72.8°C
• PSA: 17.07000
• Density: 0.95g/cm³
• LogP: 2.25760
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

99%, ^*data from raw suppliers

(1R,2S,5S)-2,6,6-TRIMETHYL BICYCLO-[3,1,1]-HEPTAN-3-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC(C2(C)C)CC1=O
• Isomeric SMILES: C[C@@H]1[C@@H]2C[C@@H](C2(C)C)CC1=O

Technology Process of Pinocamphone

There total 14 articles about Pinocamphone 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: 50.0%

α-pinene epoxide (1686-14-2,25488-94-2) → campholenyc aldehyde (4501-58-0,23727-15-3,91200-86-1,91819-58-8) + pinocarveol (547-61-5,1674-08-4,2158-49-8,3917-59-7,5947-36-4,6712-79-4,19889-99-7,19894-98-5) + iso-pinocamphone (473-62-1,547-60-4,14575-93-0,15358-88-0,18358-53-7,18492-59-6,22339-21-5,30469-22-8,30517-87-4)

Guidance literature:

With Zr(Ti)-2,6-naphthalendicarboxylate catalyst; In 1,2-dichloro-ethane; at 70 ℃; for 24h; Reagent/catalyst;

DOI:10.1039/c6ra23143h

Reference yield: 18.0%

2-Pinene oxide (217320-94-0,25488-94-2) → campholenyc aldehyde (4501-58-0,23727-15-3,91200-86-1,91819-58-8) + iso-pinocamphone (473-62-1,547-60-4,14575-93-0,15358-88-0,18358-53-7,18492-59-6,22339-21-5,30469-22-8,30517-87-4)

Guidance literature:

With methyl-tricarbonyl(η-cyclopentadienyl)molybdenum; In 1,2-dichloro-ethane; at 55 ℃; for 24h;

DOI:10.1016/j.jorganchem.2015.09.022

Reference yield:

2,6,6-trimethylbicyclo[3.1.1]heptane (473-55-2,4755-33-3,4795-86-2,4863-59-6,6876-13-7,10281-53-5,33626-25-4,112456-46-9,112456-47-0) → (1R*,2R*,3R*,5S*)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (51152-11-5) + iso-pinocamphone (473-62-1,547-60-4,14575-93-0,15358-88-0,18358-53-7,18492-59-6,22339-21-5,30469-22-8,30517-87-4) + pinan-2α-ol (473-54-1,4948-28-1,4948-29-2,18492-55-2,23516-36-1,25926-77-6,35408-04-9,35519-42-7,112574-21-7) + isoverbanol (473-64-3,473-65-4,515-88-8,7316-84-9,24739-64-8,35997-97-8,39166-53-5,39776-66-4,73307-11-6,94480-80-5,94480-81-6,94480-82-7,94480-83-8) + 1-acetyl-2,2-dimethyl-3-ethylcyclobutane (4951-97-7,67465-27-4) + cis-pinane-2-ol (473-54-1,4948-28-1,4948-29-2,18492-55-2,23516-36-1,25926-77-6,35408-04-9,35519-42-7,112574-21-7)

Guidance literature:

With oxygen; sodium sulfite; Product distribution; Mechanism; 1.) 70 deg C, 34 h, 2.) H₂O, 60 deg C, 4 h; other trans-pinane; var. temps.;

DOI:10.1002/prac.19923340506

upstream raw materials:

(1RS:2SR:3RS)-Pinanol-⁽³⁾

(1S*,2R*,3R*)-2,6,6-Trimethylbicyclo<3.1.1>heptan-3-ol

rac-α-pinene

Pinene

Downstream raw materials:

(-)-(2R,3R,5R)-2-hydroxy-3-pinanone

(+)-(1R,2R)-2,7,7-Trimethyl-3-oxabicyclo<4.1.1>octan-4-one

Refernces

• 1、 Bruno, Sofia M.,Gomes, Ana C.,Abrantes, Marta,Valente, Anabela A.,Pillinger, Martyn,Gon?alves, Isabel S.. "Ring-opening of epoxides promoted by organomolybdenum complexes of the type [(η5-C5H4R)Mo(CO)2(η3-C3H5)] and [(η5-C5H5)Mo(CO)3(CH2R)]". . p. 179 - 183. Retrieved 2015/10/19.
• 2、 Brose, Thomas,Pritzkow, Wilhelm,Thomas, Gerda. "Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen". . p. 403 - 409. Retrieved 2007/10/02.