(3R-trans)-3-Methyl-6-(1-methylvinyl)cyclohexene

Base Information

• Chemical Name: (3R-trans)-3-Methyl-6-(1-methylvinyl)cyclohexene
• CAS No.: 5113-87-1
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 2902199090
• European Community (EC) Number: 225-843-3
• DSSTox Substance ID: DTXSID70199152
• Nikkaji Number: J85.994J
• Wikidata: Q72485409
• Mol file: 5113-87-1.mol

Synonyms:5113-87-1;(1R)-(+)-trans-Isolimonene;(+)-trans-Isolimonene;(3R-trans)-3-Methyl-6-(1-methylvinyl)cyclohexene;(3R,6R)-3-methyl-6-prop-1-en-2-ylcyclohexene;EINECS 225-843-3;Cyclohexene, 3-methyl-6-(1-methylethenyl)-, (3R-trans)-;p-Mentha-2,8-diene, (1R,4R)-(+)-;Isolimonene, trans-(+)-;(+)-3R-trans-Isolimonene;(+)-(1R,4R)-trans-Isolimonene;(1R)-trans-isolimonene;3-Isopropenyl-6-methyl-1-cyclohexene-, (3R-trans)-;CHEBI:90014;DTXSID70199152;HY-N7250;AKOS017343718;p-Mentha-2,8-diene, (1R,4R)-()-;CS-0110667;(3r-trans)-3-methyl-6-(1-methylethenyl) cyclohexene;(3R-trans)-3-methyl-6-(1-methylethenyl)cyclohexene;(3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene;(1R)-(+)-trans-Isolimonene, >=95.0% (sum of enantiomers, GC)

Chemical Property of (3R-trans)-3-Methyl-6-(1-methylvinyl)cyclohexene

Chemical Property:

• Vapor Pressure: 2.26mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Boiling Point: 167.3°Cat760mmHg
• Flash Point: 41.3°C
• PSA: 0.00000
• Density: 0.824g/cm³
• LogP: 3.16480
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 153

Purity/Quality:

99%, ^*data from raw suppliers

(1R)-(+)-trans-Isolimonene ≥95.0% (sum of enantiomers, GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 2073245
• Hazard Codes: Xn,N
• Statements: 10-51/53-22
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C=C1)C(=C)C
• Isomeric SMILES: C[C@@H]1CC[C@H](C=C1)C(=C)C

Technology Process of (3R-trans)-3-Methyl-6-(1-methylvinyl)cyclohexene

There total 25 articles about (3R-trans)-3-Methyl-6-(1-methylvinyl)cyclohexene 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:

methanol (67-56-1) + isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → 3-methyl-6-(prop-1-en-2-yl)cyclohexene (5113-87-1) + 8-methoxymenthan-3-ol + 3-(2-methoxypropan-2-yl)-6-methylcyclohexene

Guidance literature:

In toluene; under 3750.38 Torr; Flow reactor;

DOI:10.1007/s00706-021-02778-8

Reference yield:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone (5524-05-0) → 3-methyl-6-(prop-1-en-2-yl)cyclohexene (5113-87-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / paraffin oil; tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Reflux

3.1: manganese(IV) oxide / dichloromethane / 64 h / 20 °C

4.1: 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / chloroform / 18 h / -30 °C

5.1: n-butyllithium / diethyl ether; hexane / 0.5 h / 0 - 20 °C

5.2: 16 h / 0 - 20 °C

6.1: chromium(VI) oxide; tert.-butylhydroperoxide / dichloromethane / 2 h

7.1: methanol / 18 h / 20 °C / Irradiation; Inert atmosphere

With chromium(VI) oxide; tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; paraffin oil; 1.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1055/s-0036-1588645

Reference yield:

ethyl (E)-2-[(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexylidene]acetate (141277-82-9) → 3-methyl-6-(prop-1-en-2-yl)cyclohexene (5113-87-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Reflux

2.1: manganese(IV) oxide / dichloromethane / 64 h / 20 °C

3.1: 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / chloroform / 18 h / -30 °C

4.1: n-butyllithium / diethyl ether; hexane / 0.5 h / 0 - 20 °C

4.2: 16 h / 0 - 20 °C

5.1: chromium(VI) oxide; tert.-butylhydroperoxide / dichloromethane / 2 h

6.1: methanol / 18 h / 20 °C / Irradiation; Inert atmosphere

With chromium(VI) oxide; tert.-butylhydroperoxide; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2-tert-butyl-3-methyl-4-oxoimidazolidin-1-ium trifluoroacetate; In methanol; diethyl ether; hexane; dichloromethane; chloroform;

DOI:10.1055/s-0036-1588645

upstream raw materials:

2-trans-Amino-3-ref-(CH₃)-trans-caran

2-carene

methanol

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

Downstream raw materials:

1-methyl-4-isopropyl-1,3-cyclohexadiene

crithmene

formaldehyd

formic acid

Refernces

• 1、 Griesbeck, Axel G.,Porschen, Bj?rn,Kropf, Christian,Landes, Agnieszka,Hinze, Olga,Huchel, Ursula,Gerke, Thomas. "Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release". . p. 539 - 553. Retrieved 2017/01/25.