trans-Verbenol

Base Information

• Chemical Name: trans-Verbenol
• CAS No.: 22339-08-8
• Deprecated CAS: 5416-53-5
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2906199090
• European Community (EC) Number: 244-920-2,217-335-5
• UNII: 3GPQ3N9L8Q,5E8197JSI1
• DSSTox Substance ID: DTXSID60883755
• Nikkaji Number: J259.681D
• Wikidata: Q82862592
• Mol file: 22339-08-8.mol

Synonyms:trans-Verbenol;22339-08-8;Verbenol, (R)-trans-;(1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol;(+)-trans-verbenol;(-)-trans-Verbenol;1820-09-3;UNII-3GPQ3N9L8Q;3GPQ3N9L8Q;Verbenol, (+/-)-trans-;UNII-5E8197JSI1;5E8197JSI1;EINECS 217-335-5;EINECS 244-920-2;AI3-23133;Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2S,5R)-rel-;Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2S,5R)-rel-;2-Pinen-4-ol, trans-;[1R-(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;(1R-(1alpha,2alpha,5alpha))-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol;NSC-6833;VERBENOL, TRANS-;(1R)-TRANS-VERBENOL;SCHEMBL1065045;(+/-)-TRANS-VERBENOL;(1alpha,2alpha,5alpha)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol;DTXSID60883755;VERBENOL, R-(+)-TRANS-;NSC 6833;TRANS-VERBENOL, (+/-)-;2-PINEN-4-OL, TRANS-(+)-;A816390;(1R,2S,5R)-4,6,6-trimethyl-2-bicyclo[3.1.1]hept-3-enol;4,6,6-TRIMETHYL-, (1.ALPHA.,2.ALPHA.,5.ALPHA.)-;Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, trans-(+)-;BICYCLO(3.1.1)HEPT-3-EN-2-OL, 4,6,6-TRIMETHYL-, (1R,2S,5R)-

Chemical Property of trans-Verbenol

Chemical Property:

• Boiling Point: 214.9°Cat760mmHg
• Flash Point: 84.5°C
• PSA: 20.23000
• Density: 1.002g/cm³
• LogP: 1.96950
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

(+)-trans-Verbenol ^*data from reagent 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
• Uses: (+)-trans-Verbenol is synthesized as an inhibitor of Parkinsons disease.

Technology Process of trans-Verbenol

There total 111 articles about trans-Verbenol 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:

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

2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-ol acetate

(+)-cis-pinononoic acid

4-methylisopropylbenzene

Refernces

A short synthesis of (-)-dendrobine

10.1021/ja990707p

The research focuses on the concise, enantioselective synthesis of (-)-dendrobine (1), a major alkaloid constituent of the Chinese ornamental orchid Dendrobium nobile, known for its antipyretic and hypotensive activities. The purpose of the study was to develop an efficient and stereoselective synthetic route to this molecule, which was achieved in 13 steps, starting from (+)-trans-verbenol (6). The synthesis involved a cascade reaction with a carbamyl radical to form amino alcohol 3, establishing the three principal stereogenic centers. Key chemicals used in the process included Pauson-Khand reaction components, such as N-propargyl derivative 8, and various reagents for functional group transformations, like iodotrimethylsilane, phenylselenenyl bromide, diethylaluminum cyanide, and sodium borohydride. The synthesis concluded with the formation of (-)-dendrobine (1) from cyanoketone 13 through a series of reactions, including reduction, Barton-McCombie deoxygenation, and epimerization, ultimately yielding the target compound with a 75% overall yield from 14 based on the recovered 15b. The study also highlighted the intriguing solvent effect on the Pauson-Khand reaction and the efficient formation of the azatricyclo[6.2.1.04,11]undecane ring system.