(1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

Base Information

• Chemical Name: (1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
• CAS No.: 1820-09-3
• Deprecated CAS: 1414586-51-8
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• European Community (EC) Number: 217-335-5,243-407-0
• UNII: R7N6NH1O0K
• DSSTox Substance ID: DTXSID10885103
• Nikkaji Number: J259.680F
• Wikidata: Q27287910
• Mol file: 1820-09-3.mol

Synonyms:19890-02-9;(1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol;Verbenol, (S)-trans-;(S)-trans-verbenol;UNII-R7N6NH1O0K;R7N6NH1O0K;(1S)-(+)-Cis-verbenol;EINECS 243-407-0;AI3-23135;Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1S,2R,5S)-;Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1S,2R,5S)-;[1S-(1alpha,2alpha,5alpha)]-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol;(1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol;2-Pinen-4-ol, trans-;1820-09-3;Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1.alpha.,2.alpha.,5.alpha.)-;Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, [1S-(1.alpha.,2.alpha.,5.alpha.)]-;BICYCLO(3.1.1)HEPT-3-EN-2-OL, 4,6,6-TRIMETHYL-, (1S-(1.ALPHA.,2.ALPHA.,5.ALPHA.))-;(1S)-TRANS-VERBENOL;SCHEMBL19951524;DTXSID10885103;(1S-(1alpha,2alpha,5alpha))-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol;Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, [1S-(1.alpha.,2.beta.,5.alpha.)]-;(S)-(-)-TRANS-VERBENOL;AKOS006272684;(1S,4R,5S)-(-)-TRANS-VERBENOL;2-PINEN-4-OL, (1S,4R,5S)-(-)-;4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol #;Q27287910;(1S,5alpha)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2alpha-ol;Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, trans-(-)-

Chemical Property of (1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

Chemical Property:

• Melting Point: 24°C
• Refractive Index: 1.4908 (estimate)
• Boiling Point: 234.73°C (rough estimate)
• PKA: 14.56±0.60(Predicted)
• Flash Point: 84.51oC
• PSA: 20.23000
• Density: 0.9657
• LogP: 1.96950
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 215

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(C2CC1C2(C)C)O
• Isomeric SMILES: CC1=C[C@H]([C@H]2C[C@@H]1C2(C)C)O

Technology Process of (1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

There total 83 articles about (1S,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-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: 54.0%

Pinene (80-56-8,177698-18-9,25766-18-1) → verbenone (80-57-9) + Verbenol (1820-09-3,1845-30-3,5416-53-5,13040-03-4,18881-04-4,19890-02-9,22339-08-8,80795-83-1,473-67-6)

Guidance literature:

With oxygen; Enzymatic reaction;

DOI:10.1016/j.molcatb.2015.02.006

Reference yield: 29.0%

Pinene (80-56-8,177698-18-9,25766-18-1) → verbenone (80-57-9) + Verbenol (1820-09-3,1845-30-3,5416-53-5,13040-03-4,18881-04-4,19890-02-9,22339-08-8,80795-83-1,473-67-6) + pinocarveyl hydroperoxide (22321-84-2) + verbenyl-hydroperoxide (94268-68-5) + α-pinene epoxide (1686-14-2,25488-94-2)

Guidance literature:

With oxygen; at 89.84 ℃; under 750.075 Torr;

DOI:10.1002/cssc.200900228

Reference yield:

Pinene (80-56-8,177698-18-9,25766-18-1) → verbenone (80-57-9) + Verbenol (1820-09-3,1845-30-3,5416-53-5,13040-03-4,18881-04-4,19890-02-9,22339-08-8,80795-83-1,473-67-6) + 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) + sobrerol (498-71-5,454-77-3,772-36-1,32226-54-3,38235-58-4,42370-41-2,54164-89-5,60687-00-5,71697-84-2)

Guidance literature:

With Acetobacter methanolicus MB 58; microbielle oxydation;

upstream raw materials:

Pinene

rac-α-pinene

dihydrogen peroxide

acetone

Downstream raw materials:

benzyl-((1S,4R)-pin-2-en-4-yl)-ether

(-)-(S)-2,2,4-trimethyl-3-cyclohexene-1-carbaldehyde

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-yloxy)-tetrahydro-pyran-3-yl ester

(+/-)-4-trans-(2-Olivetyl)-pinen

Refernces

• 1、 Aberkouks, Abderrazak,Mekkaoui, Ayoub Abdelkader,Ait Ali, Mustapha,El Firdoussi, Larbi,El Houssame, Soufiane. "Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst". . . Retrieved 2020/02/15.
• 2、 Karman, Marta,Romanowski, Grzegorz. "Cis-dioxidomolybdenum(VI) complexes with chiral tetradentate Schiff bases: Synthesis, spectroscopic characterization and catalytic activity in sulfoxidation and epoxidation". . . Retrieved 2020/07/02.