2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol

Base Information

• Chemical Name: 2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
• CAS No.: 5989-33-3
• Deprecated CAS: 10448-30-3,128441-08-7,17681-23-1,21391-92-4,37267-79-1,63427-76-9,68780-91-6
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• European Community (EC) Number: 227-814-0
• UNII: 2U90CGE5DT
• Nikkaji Number: J221.269B
• Wikidata: Q27160941
• Metabolomics Workbench ID: 49144
• ChEMBL ID: CHEMBL2252948
• Mol file: 5989-33-3.mol

Synonyms:cis-Linalool Oxide;2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol;cis-Linalool 3,6-oxide;(+/-)-cis-Linalyl oxide;2U90CGE5DT;(Z)-Furanoid linalool oxide;CHEBI:88903;cis-alpha,alpha,5-Trimethyl-5-vinyltetrahydrofuran-2-methanol;cis-Linalyl Oxide;5989-33-3;Linalool oxide, (Z)-;Linalool oxide B;Linalool oxide, cis-;(Z)-Linalool oxide B;cis-Furan linalool oxide;UNII-2U90CGE5DT;Linalool oxide I (cis, furanoid);EINECS 227-814-0;Linalool oxide I;CIS-FURANOID;(2R,5S)-linalyl oxide;cis-Furanoid linalool oxide;CIS-F-LINALOOL OXIDE;linalool oxide B (cis-THF);cis-5-Ethenyltetrahydro-alpha,alpha,5-trimethyl-2-furanmethanol;EPOXYDIHYDROLINALOOL II;SCHEMBL111540;2-Furanmethanol, 5-ethenyltetrahydro-alpha,alpha,5-trimethyl-, cis-;cis-2-Methyl-2-vinyl-5-(1-hydroxy-1-methylethyl)tetrahydrofuran;CHEMBL2252948;(2S,5R)-(+)-Linalool oxide;2-Furanmethanol, 5-ethenyltetrahydro-alpha,alpha,5-trimethyl-, (2R,5S)-rel-;BRHDDEIRQPDPMG-PSASIEDQSA-N;CHEBI:132839;FEMA NO. 3746, CIS-;(+/-)-LINALOOL OXIDE, (Z)-;Q27160941;5-Ethenyltetrahydro-a,a,5-trimethyl-cis-2-Furanmethanol;5-Ethenyltetrahydro-a,a,5-trimethyl-(2R,5S)-rel-2-Furanmethanol

Chemical Property of 2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol

Chemical Property:

• Boiling Point: 188 °C
• PKA: 14.57±0.29(Predicted)
• Flash Point: 75.4oC
• PSA: 29.46000
• Density: 1.023±0.06 g/cm3(Predicted)
• LogP: 1.88100
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

99%, ^*data from raw suppliers

cis-LinaloolOxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(O1)C(C)(C)O)C=C
• Isomeric SMILES: C[C@]1(CC[C@@H](O1)C(C)(C)O)C=C

Technology Process of 2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol

There total 28 articles about 2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-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: 60.0%

anti-N-<1-(5-ethenyltetrahydro-5-methylfuran-2-yl)-1-methylethoxy>-2,2,6,6-tetramethylpiperidine (128344-89-8,128344-91-2) → 2-[(5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propan-2-ol (4031-48-5,5989-33-3,23007-29-6,34995-77-2,41720-55-2,41720-60-9,60047-17-8,128441-08-7,128441-10-1,37267-80-4)

Guidance literature:

With acetic acid; zinc;

DOI:10.1039/c39900000103

Reference yield:

Carbonic acid (Z)-6,7-dihydroxy-3,7-dimethyl-oct-2-enyl ester methyl ester → 2-[(5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propan-2-ol (4031-48-5,5989-33-3,23007-29-6,34995-77-2,41720-55-2,41720-60-9,60047-17-8,128441-08-7,128441-10-1,37267-80-4) + trans-2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (4031-48-5,5989-33-3,23007-29-6,34995-77-2,41720-55-2,41720-60-9,60047-17-8,128441-08-7,128441-10-1,37267-80-4)

Guidance literature:

With triphenylphosphine; palladium diacetate; In tetrahydrofuran; at 50 ℃; for 24h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(97)00130-0

Reference yield:

Carbonic acid (Z)-6,7-dihydroxy-3,7-dimethyl-oct-2-enyl ester methyl ester → 2-[(5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propan-2-ol (4031-48-5,5989-33-3,23007-29-6,34995-77-2,41720-55-2,41720-60-9,60047-17-8,128441-08-7,128441-10-1,37267-80-4) + trans-2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (4031-48-5,5989-33-3,23007-29-6,34995-77-2,41720-55-2,41720-60-9,60047-17-8,128441-08-7,128441-10-1,37267-80-4)

Guidance literature:

With triphenylphosphine; palladium diacetate; In tetrahydrofuran; at 50 ℃; for 24h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(97)00130-0

upstream raw materials:

anti-N-<1-(5-ethenyltetrahydro-5-methylfuran-2-yl)-1-methylethoxy>-2,2,6,6-tetramethylpiperidine

Carbonic acid (E)-6,7-dihydroxy-3,7-dimethyl-oct-2-enyl ester ethyl ester

3,7-dimethylocta-1,6-dien-3-ol

Nerol

Refernces

• 1、 van Lint, Matthijs J.,Gümüs, Aysegül,Ruijter, Eelco,Faber, Kurt,Orru, Romano V. A.,Hall, Mélanie. "Enantioselective Bio-Hydrolysis of Geranyl-Derived rac-Epoxides: A Chemoenzymatic Route to trans-Furanoid Linalool Oxide". . p. 813 - 825. Retrieved 2019/01/04.
• 2、 Snejko, Natalia,Cascales, Concepcion,Gomez-Lor, Berta,Gutierrez-Puebla, Enrique,Iglesias, Marta,Ruiz-Valero, Caridad,Monge, M. Angeles. "From rational octahedron design to reticulation serendipity. A thermally stable rare earth polymeric disulfonate family with CdI2-like structure, bifunctional catalysis and optical properties". . p. 1366 - 1367. Retrieved 2007/10/03.