2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol

Base Information

• Chemical Name: 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol
• CAS No.: 473-61-0
• Molecular Formula: C10H18O
• European Community (EC) Number: 207-468-7
• NSC Number: 167499
• Nikkaji Number: J196.195K
• Wikidata: Q105235007
• Mol file: 473-61-0.mol

Synonyms:2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol;3-Pinanol;473-61-0;Isopinocampheol;3-Pinanol, stereoisomer;25465-65-0;EINECS 207-468-7;(1R,2R,3R,5S)-(-)-Isopinocampheol;2,6,6-Trimethylbicyclo(3.1.1)heptan-3-ol;4,6,6-trimethyl-3-bicyclo[3.1.1]heptanol;Bicyclo[3.1.1]heptan-3-ol, 2,6,6-trimethyl-, (1.alpha.,2.beta.,3.alpha.,5.alpha.)-;CC1(C)C2CC(O)C(C)C1C2;MFCD00064146;2,6,6-trimethylnorpinan-3-ol;pinan-3-ol;4,6,6-trimethylbicyclo[3.1.1]heptan-3-ol;SCHEMBL220765;AMY14854;NSC167499;AKOS000120849;HY-W048972;NSC-167499;SB84220;SY096803;CS-0101284;FT-0633460;FT-0652505;FT-0655607;(1R, 2R, 3R, 5S)-(-)-isopiriocampheol;EN300-20761;2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol #;A817867;A819190;A921806;J-500295;J-500440;(1R,2R,3R,5S)-2,6,6-trimethyl-bicyclo[3.1.1]Hept-3-ol;(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]Heptan-3-ol;Bicyclo[3.1.1]heptan-3-ol, 2,6,6-trimethyl-, (1.alpha.,2.beta.,3.beta.,5.alpha.)-;Bicyclo[3.1.1]heptan-3-ol,6,6-trimethyl-, (1.alpha.,2.beta.,3.alpha.,5.alpha.)-;Bicyclo[3.1.1]heptan-3-ol, 2,6,6-trimethyl-, [1R-(1.alpha.,2.alpha.,3.beta.,5.alpha.)]-;Bicyclo[3.1.1]heptan-3-ol, 2,6,6-trimethyl-, [1R-(1.alpha.,2.beta.,3.beta.,5.alpha.)]-;Bicyclo[3.1.1]heptan-3-ol, 2,6,6-trimethyl-, [1S-(1.alpha.,2.beta.,3.alpha.,5.alpha.)]-

Chemical Property of 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C2CC(C2(C)C)CC1O

Technology Process of 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol

There total 39 articles about 2,6,6-Trimethylbicyclo[3.1.1]heptan-3-ol 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: 90.0%

(-)-α-pinene (7785-26-4,25766-18-1) → (+)-isopinocampheol (1196-00-5,2734-31-8,19889-94-2,19889-95-3,25465-65-0,25465-95-6,27779-29-9,35997-96-7,35998-01-7,36129-11-0,51152-11-5,73366-08-2,125473-76-9,473-61-0,24041-60-9)

Guidance literature:

(-)-α-pinene; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; for 1h; Heating;

DOI:10.1016/S0957-4166(99)00446-2

Reference yield: 70.0%

B-crotyldiisopinocampheylborane (99493-12-6) + (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-pentanal (344796-28-7) → (+)-isopinocampheol (1196-00-5,2734-31-8,19889-94-2,19889-95-3,25465-65-0,25465-95-6,27779-29-9,35997-96-7,35998-01-7,36129-11-0,51152-11-5,73366-08-2,125473-76-9,473-61-0,24041-60-9) + (3R,4R,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-3,5-dimethyl-oct-1-en-4-ol (344796-32-3) + (3S,4R,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-3,5-dimethyl-oct-1-en-4-ol (344796-33-4)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; Heating;

DOI:10.1016/j.tetlet.2007.08.075

Reference yield: 43.0%

C13H20O (1058019-16-1) → (+)-isopinocampheol (1196-00-5,2734-31-8,19889-94-2,19889-95-3,25465-65-0,25465-95-6,27779-29-9,35997-96-7,35998-01-7,36129-11-0,51152-11-5,73366-08-2,125473-76-9,473-61-0,24041-60-9)

Guidance literature:

With samarium diiodide; water; isopropylamine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2008.06.081

upstream raw materials:

6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol

(1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane

(-)-α-pinene

cyclohexane

Downstream raw materials:

isopinocamphone

phthalic acid mono-((1S:2S:3S)-pinanyl-⁽³⁾-ester)

4-methyl-3-penten-1-al

dihydrocarveol

Refernces

Synthesis of enantiopure C₁ symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones

10.1016/S0957-4166(01)00175-6

The research focuses on the synthesis of enantiopure C1 symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones, which are valuable in asymmetric catalysis using coordination complexes of transition metals. The study utilizes various reactants, including 2-(diphenylphosphino)phenylphosphonous acid tetramethyldiamide, (+)-menthol, (1S,2S,3S,5R)-isopinocampheol, and (1R,2R)-trans-cyclohexanediol, to produce enantiopure phosphino-phosphonite ligands. The experiments involve Pd-catalyzed P–C coupling, halogen–metal exchange, and metallation–alkylation procedures. X-ray structural analysis was employed to determine the structures of the synthesized compounds, and various analytical techniques such as 31P{1H} NMR, 13C{1H} NMR, and optical rotation measurements were used to characterize the products and confirm the success of the reactions.

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