2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

Base Information

• Chemical Name: 2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
• CAS No.: 10136-65-9
• Molecular Formula: C10H16 O2
• Molecular Weight: 168.236
• European Community (EC) Number: 233-376-1
• DSSTox Substance ID: DTXSID90871948
• Nikkaji Number: J10.649F
• Mol file: 10136-65-9.mol

Synonyms:Oxypinocamphone;Oxypinone;2-Hydroxy-3-pinanone;Camphostene;10136-65-9;3-Hydroxypinocamphone;2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one;3-Pinanone, 2-hydroxy-;2-Hydroxypinan-3-one;EINECS 233-376-1;(+)-2-Hydroxypinocamphone;2-Hydroxy-2,6,6-trimethylbicyclo(3.1.1)heptan-3-one;OPC;Bicyclo(3.1.1)heptan-3-one, 2-hydroxy-2,6,6-trimethyl-;Bicyclo[3.1.1]heptan-3-one, 2-hydroxy-2,6,6-trimethyl-;(+)-2-hydroxy-3-pinanone;2-hydroxy-pinanone;4-hydroxy-4,6,6-trimethylbicyclo[3.1.1]heptan-3-one;SCHEMBL1649604;DTXSID90871948;AKOS024386579;3-Pinanone, 2-hydroxy-, (.+.)-;(1R,2R,5R)-(+)-Hydroxy-3-pinanone;LS-109796;CS-0279238;FT-0604408;FT-0670009;EN300-297194;Q-200009;(3-BOC-AMINO-PYRROLIDIN-1-YL)-THIOPHEN-2-YL-ACETICACID

Chemical Property of 2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

Chemical Property:

• Vapor Pressure: 0.00491mmHg at 25°C
• Melting Point: 38.5 °C
• Boiling Point: 245°C at 760 mmHg
• PKA: 12.93±0.40(Predicted)
• Flash Point: 104.5°C
• PSA: 37.30000
• Density: 1.081g/cm³
• LogP: 1.37250
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 244

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C2CC1C(C(=O)C2)(C)O)C
• Recent ClinicalTrials: AGE Levels in ER+ Metastatic Breast Cancer Patients Receiving Endocrine Therapy

Technology Process of 2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

There total 31 articles about 2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 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: 98.0%

(2S,4S)-2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-4-trimethylsilanyloxy-pentanoic acid tert-butyl ester → (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1) + (2S,4S)-2-Amino-4-hydroxy-pentanoic acid tert-butyl ester

Guidance literature:

With citric acid; In tetrahydrofuran; for 96h; Ambient temperature;

DOI:10.1055/s-1997-3246

Reference yield: 72.0%

(-)-α-pinene (7785-26-4,25766-18-1) → (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1)

Guidance literature:

With potassium permanganate; water; In acetone; at -10 ℃;

DOI:10.1016/j.tetlet.2015.12.042

Reference yield: 62.0%

tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate (276253-82-8) + 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate (329710-76-1) → (S)-tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]-heptan-3-ylidene)amino]-4-(trifluoromethoxy)butanoate + (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1)

Guidance literature:

tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

2-(trifluoromethoxy)ethyl trifluoromethanesulphonate; In tetrahydrofuran; at -78 - 20 ℃; Overall yield = 1.34 g; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c6ob02436j

upstream raw materials:

(-)-α-pinene

(1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one

isopinocamphone

(+)-α-pinene

Downstream raw materials:

[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(2S)-2,6,6-trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol

(2R)-2,6,6-trimethyl-3-(pyridin-3-ylmethylimino)bicyclo[3.1.1]heptan-2-ol

Refernces

• 1、 Kondratov, Ivan S.,Logvinenko, Ivan G.,Tolmachova, Nataliya A.,Morev, Roman N.,Kliachyna, Maria A.,Clausen, Florian,Daniliuc, Constantin G.,Haufe, Günter. "Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid-a CF3O-containing analogue of natural lipophilic amino acids". . p. 672 - 679. Retrieved 2017.
• 2、 Suga et al.. "-". . p. 1180,1183. Retrieved 1968.
• 3、 Dvornikova,Buravlev,Suponitskii,Chukicheva,Kutchin. "Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction". . p. 480 - 492. Retrieved 2015.
• 4、 Frensch, Gustavo,Labes, Ricardo,Wosch, Celso Luiz,Munaretto, Laieli Dos Santos,Salomé, Kahlil Schwanka,Guerrero, Palimécio G.,Marques, Francisco A.. "New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes". . p. 420 - 422. Retrieved 2016.
• 5、 Hoeld,Sirisoma,Sparks,Casida. "Metabolism and mode of action of cis- and trans-3-pinanones (the active ingredients of hyssop oil)". . p. 251 - 265. Retrieved 2002.