(+)-cis-Rose oxide

Base Information

• Chemical Name: (+)-cis-Rose oxide
• CAS No.: 4610-11-1
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• European Community (EC) Number: 225-017-2,618-036-6
• UNII: 08FS7459GK,7G7H98N31J
• DSSTox Substance ID: DTXSID401033220,DTXSID50894739
• Nikkaji Number: J297.847D
• Wikidata: Q27162313
• Mol file: 4610-11-1.mol

Synonyms:(+)-cis-rose oxide;Rose oxide, (-)-;UNII-08FS7459GK;4610-11-1;876-17-5;08FS7459GK;(2R,4S)-rose oxide;Rose oxide, cis-(+)-;FEMA No. 3236, (-)-;(2R-cis)-Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran;7G7H98N31J;Rose oxide L;2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2R,4S)-rel-;CIS-ROSENOXIDE;cis-(+)-rose oxide;D-CIS-ROSE OXIDE;UNII-C6O879WVH2;(2R,4S)-4-methyl-2-(2-methylprop-1-enyl)oxane;UNII-7G7H98N31J;SCHEMBL3663078;CHEBI:90102;(+/-)-CIS-ROSE OXIDE;DTXSID50894739;CZCBTSFUTPZVKJ-UWVGGRQHSA-N;DTXSID401033220;EINECS 225-017-2;ROSE OXIDE, CIS-(+/-)-;(4S,2R)-(+)-ROSE OXIDE;FEMA NO. 3236, CIS-(+)-;FEMA NO. 3236, CIS-(+/-)-;Q27162313;cis-tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran;(2R,4S)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran;2H-PYRAN, TETRAHYDRO-4-METHYL-2-(2-METHYLPROPENYL)-, CIS-;(+)-(2R,4S)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran;(2R,4S)-(+)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran;2H-PYRAN, TETRAHYDRO-4-METHYL-2-(2-METHYL-1-PROPENYL)-, CIS-;2H-PYRAN, TETRAHYDRO-4-METHYL-2-(2-METHYLPROPENYL)-, CIS-(+)-;2H-PYRAN, TETRAHYDRO-4-METHYL-2-(2-METHYL-1-PROPEN-1-YL)-, (2R,4S)-;2H-PYRAN, TETRAHYDRO-4-METHYL-2-(2-METHYL-1-PROPENYL)-, (2R-CIS)-

Chemical Property of (+)-cis-Rose oxide

Chemical Property:

• Vapor Pressure: 0.551mmHg at 25°C
• Boiling Point: 196.7°C at 760 mmHg
• Flash Point: 66.8°C
• PSA: 9.23000
• Density: 0.909g/cm³
• LogP: 2.76770
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCOC(C1)C=C(C)C
• Isomeric SMILES: C[C@H]1CCO[C@H](C1)C=C(C)C

Technology Process of (+)-cis-Rose oxide

There total 44 articles about (+)-cis-Rose oxide 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: 75.0%

(2R,4S)-2-((E)-3-Bromo-2-methyl-propenyl)-4-methyl-tetrahydro-pyran (144867-81-2) → cis‐rose oxide (4610-11-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 6h; Heating;

DOI:10.1016/S0040-4020(01)88272-7

Reference yield:

(+)-(R)-4-methylidene-2,2'-methylprop-1'-enyl-tetrahydropyran (76936-34-0) → cis‐rose oxide (4610-11-1) + (-)-trans-Rose oxide (5258-11-7)

Guidance literature:

With Wilkinson's catalyst; hydrogen; In benzene; at 20 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1021/ja060812g

Reference yield:

Dimethyl-[(R)-2-(2-methyl-propenyl)-tetrahydro-pyran-(4E)-ylidenemethyl]-phenyl-silane (895153-44-3) → cis‐rose oxide (4610-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAF; DMSO / tetrahydrofuran / 1 h / 90 °C

2: ClRh(PPh₃)3; H₂ / benzene / 3 h / 20 °C

With Wilkinson's catalyst; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; In tetrahydrofuran; benzene;

DOI:10.1021/ja060812g

upstream raw materials:

(2R,4S)-2-((E)-3-Bromo-2-methyl-propenyl)-4-methyl-tetrahydro-pyran

triphenylphosphonio-1-methylethanide

Trifluoro-acetic acid ((2R,4S)-4-methyl-tetrahydro-pyran-2-yl)-phenylsulfanyl-methyl ester

(3R)-3,7-dimethyl-5,6-octadien-1-ol

Refernces

• 1、 Eschinasi,E.H.. "". . p. 1097 - 1100. Retrieved 1970.
• 2、 Trost, Barry M.,Machacek, Michelle R.,Faulk, Brian D.. "Sequential Ru-Pd catalysis: A two-catalyst one-pot protocol for the synthesis of N- and O-heterocycles". . p. 6745 - 6754. Retrieved 2007/10/03.
• 3、 -. "Process for producing a rose oxide". . . Retrieved 2008/06/13.