(1r,3s,5r)-6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol

Base Information

• Chemical Name: (1r,3s,5r)-6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
• CAS No.: 19894-98-5
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2906199090
• European Community (EC) Number: 216-813-0,243-410-7
• UNII: 993483H55R,20ZI248IAP
• DSSTox Substance ID: DTXSID301339508
• Nikkaji Number: J217.756K
• Wikidata: Q105150076
• Mol file: 19894-98-5.mol

Synonyms:19894-98-5;(1r,3s,5r)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol;trans-Pinocarveol;Pinocarveol, trans-(+)-;UNII-20ZI248IAP;Pinocarveol, trans-(+/-)-;20ZI248IAP;2(10)-Pinen-3-ol, trans-;1674-08-4;UNII-993483H55R;EINECS 216-813-0;EINECS 243-410-7;993483H55R;(1R,3S,5R)-3-Hydroxy-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane;(1alpha,3alpha,5alpha)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol;[1R-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol;(1alpha,3alpha,5alpha)-6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol;(1R-(1alpha,3beta,5alpha))-6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol;Bicyclo[3.1.1]heptan-3-ol, 6,6-dimethyl-2-methylene-, (1.alpha.,3.alpha.,5.alpha.)-;BICYCLO(3.1.1)HEPTAN-3-OL, 6,6-DIMETHYL-2-METHYLENE-, (1.ALPHA.,3.ALPHA.,5.ALPHA.)-;trans-Isopinocarveol;(+)-trans-Pinocarveol;(+)-PINOCARVEOL;D-TRANS-PINOCARVEOL;PINOCARVEOL, TRANS-;TRANS-(+)-PINOCARVEOL;SCHEMBL14484474;DTXSID301339508;(-)-trans-2(10)-Pinen-3-ol;(1R)-(+)-TRANS-PINOCARVEOL;AKOS026742394;FEMA NO. 3587, TRANS-(+)-;FEMA NO. 3587, TRANS-(+/-)-;BICYCLO(3.1.(+/-)-TRANS-PINOCARVEOL;EN300-183424;(1S,3R,5S)-(-)-2(10)-Pinen-3-ol;2(10)-PINEN-3-OL, (1R,3S,5R)-(+)-;BICYCLO(3.1.1)HEPTAN-3-OL, 6,6-DIMETHYL-2-METHYLENE-, (1R,3S,5R)-;BICYCLO(3.1.1)HEPTAN-3-OL, 6,6-DIMETHYL-2-METHYLENE-, (1R,3S,5R)-REL-;BICYCLO(3.1.1)HEPTAN-3-OL, 6,6-DIMETHYL-2-METHYLENE-, (1R-(1.ALPHA.,3.ALPHA.,5.ALPHA.))-

Chemical Property of (1r,3s,5r)-6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol

Chemical Property:

• Vapor Pressure: 0.0283mmHg at 25°C
• Boiling Point: 217.5°Cat760mmHg
• Flash Point: 90.1°C
• PSA: 20.23000
• Density: 1g/cm³
• LogP: 1.96950
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

97% ^*data from raw suppliers

(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CC1C(=C)C(C2)O)C
• Isomeric SMILES: CC1([C@@H]2C[C@H]1C(=C)[C@H](C2)O)C
• General Description: [1R-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol, also known as (+)-trans-pinocarveol, is a monoterpene alcohol studied in the context of dithiocarbonate synthesis and photolysis. The compound was used as a precursor to explore photolytic transformations, where it was converted into dithiocarbonates and subsequently subjected to photolysis, yielding thioethers or disulfides depending on reaction conditions. This highlights its role as a versatile intermediate in organic synthesis and photochemical studies.

Technology Process of (1r,3s,5r)-6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol

There total 73 articles about (1r,3s,5r)-6,6-Dimethyl-2-methylidenebicyclo[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: 100.0%

Pinene (80-56-8,177698-18-9,25766-18-1) → 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)

Guidance literature:

Pinene; With oxygen; In dichloromethane; at 20 ℃; for 4h; visible light irradiation;

With triphenylphosphine;

DOI:10.1039/b916488j

Reference yield: 81.0%

Pinene (80-56-8,177698-18-9,25766-18-1) → pinocarvone (16812-40-1) + 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) + C10H16O2 (18680-29-0,18680-31-4,25926-74-3,33081-45-7,33081-46-8,79951-98-7)

Guidance literature:

With titanium(IV) isopropylate; oxygen; 5,15,10,20-tetraphenylporphyrin; In dichloromethane; at 0 ℃; Irradiation;

DOI:10.1016/S0040-4039(00)84656-0

Reference yield: 63.75%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Beta-pinene (177698-19-0,25719-60-2) → nopol (128-50-7) + 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)

Guidance literature:

With Cr and Fe containing metal organic framework MIL-101; air; In acetonitrile; at 80 ℃; for 30h; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/d0ta02991b

upstream raw materials:

3-amino-β-pinene

Pinene

myrtenol

myrtenyl hydroperoxide

Downstream raw materials:

(?)-β-pinene

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

(+)-isopinocampheol

trans-pinocarvyl acetate

Refernces

Synthesis and Photolysis of S-Methyl S-Alkenyl Dithiocarbonates in the Monoterpene Series

10.1021/jo00201a024

The research focuses on the synthesis and photolysis of dithiocarbonates derived from monoterpenes, specifically myrtenol, trans-pinocarveol, and perillyl alcohol. The purpose of the study was to explore the transformations of these dithiocarbonates under photolytic conditions, aiming to understand the regioselective formation of thioethers and disulfides. The researchers synthesized the dithiocarbonates by xanthation of the parent alcohols using potassium hydroxide and carbon disulfide, followed by thermolysis or silica gel chromatography to achieve the desired dithiocarbonates. Upon photolysis at different wavelengths (254 nm and >313 nm), the primary dithiocarbonates mainly yielded disulfides, while the secondary ones primarily produced thioethers.