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5989-27-5

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5989-27-5 Usage

General Description

D-Limonene is a clear, colorless liquid at room temperature with a pleasantly distinct, strong citrus aroma. This chemical compound comes from the peel of citrus fruits and is widely used in the manufacture of food flavorings, perfume, household cleaning products, and in herbal medicine. It is highly flammable, non-toxic, and is considered an effective solvent for cleaning purposes, as well as a natural insecticide. Evidence from studies suggests possible health benefits, including anti-inflammatory, antioxidant, and anticancer properties. However, exposure to high concentrations may cause skin irritation in some individuals. It is largely categorized as safe by most regulatory agencies.

Check Digit Verification of cas no

The CAS Registry Mumber 5989-27-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,8 and 9 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 5989-27:
(6*5)+(5*9)+(4*8)+(3*9)+(2*2)+(1*7)=145
145 % 10 = 5
So 5989-27-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1

5989-27-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (L0047)  (+)-Limonene  >95.0%(GC)

  • 5989-27-5

  • 25mL

  • 205.00CNY

  • Detail
  • TCI America

  • (L0047)  (+)-Limonene  >95.0%(GC)

  • 5989-27-5

  • 500mL

  • 435.00CNY

  • Detail
  • TCI America

  • (L0105)  (+)-Limonene  >99.0%(GC)

  • 5989-27-5

  • 5mL

  • 390.00CNY

  • Detail
  • TCI America

  • (L0105)  (+)-Limonene  >99.0%(GC)

  • 5989-27-5

  • 25mL

  • 1,180.00CNY

  • Detail
  • Alfa Aesar

  • (L04733)  (R)-(+)-Limonene, 97%, stab.   

  • 5989-27-5

  • 100ml

  • 163.0CNY

  • Detail
  • Alfa Aesar

  • (L04733)  (R)-(+)-Limonene, 97%, stab.   

  • 5989-27-5

  • 500ml

  • 482.0CNY

  • Detail
  • Sigma-Aldrich

  • (62118)  (R)-(+)-Limonene  analytical standard

  • 5989-27-5

  • 62118-1ML

  • 445.77CNY

  • Detail
  • Sigma-Aldrich

  • (62118)  (R)-(+)-Limonene  analytical standard

  • 5989-27-5

  • 62118-5ML

  • 1,423.89CNY

  • Detail
  • Sigma-Aldrich

  • (62118)  (R)-(+)-Limonene  analytical standard

  • 5989-27-5

  • 62118-25ML

  • 5,647.59CNY

  • Detail
  • Sigma-Aldrich

  • (00590590)  (R)-(+)-Limonene  primary pharmaceutical reference standard

  • 5989-27-5

  • 00590590-100MG

  • 3,039.66CNY

  • Detail
  • Sigma-Aldrich

  • (62122)  (R)-(+)-Limonene  technical, ~90% (sum of enantiomers, GC)

  • 5989-27-5

  • 62122-250ML-F

  • 374.40CNY

  • Detail
  • Sigma-Aldrich

  • (62122)  (R)-(+)-Limonene  technical, ~90% (sum of enantiomers, GC)

  • 5989-27-5

  • 62122-1L-F

  • 1,137.24CNY

  • Detail

5989-27-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (4R)-limonene

1.2 Other means of identification

Product number -
Other names (R)-(+)-p-mentha-1,8-diene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances;Solvents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5989-27-5 SDS

5989-27-5Synthetic route

Phosphoric acid diethyl ester (R)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester

Phosphoric acid diethyl ester (R)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With ammonia; lithium80%
L-carveol
308363-12-4

L-carveol

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With 2-nitrobenzenesulfonyl hydrazide; triphenylphosphine; diethylazodicarboxylate In various solvent(s) -30 deg, 1 h; 23 deg C 30 min;78%
(+)-trans-carveol
2102-58-1

(+)-trans-carveol

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With triethylsilane; lithium perchlorate In diethyl ether for 16h; Ambient temperature;68%
1-[2-((R)-4-Methyl-cyclohex-3-enyl)-prop-2-ene-1-sulfonyl]-propan-2-one

1-[2-((R)-4-Methyl-cyclohex-3-enyl)-prop-2-ene-1-sulfonyl]-propan-2-one

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With aluminum amalgam In tetrahydrofuran; water at 20℃; for 4h;58%
C16H27BO2

C16H27BO2

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With acetic acid at 120℃;22%
(+)-α-pinene
7785-70-8

(+)-α-pinene

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With fired clay at 25℃;
With fired clay; acetic anhydride; acetic acid at 10℃;
With fired clay; acetic anhydride; acetic acid at 25℃;
2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

benzene
71-43-2

benzene

A

D-limonene
5989-27-5

D-limonene

B

bornyl-picryl ether

bornyl-picryl ether

C

(+)-camphene
79-92-5

(+)-camphene

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
at 120℃; d-α-pinene;
2-Benzoylbenzoic acid
85-52-9

2-Benzoylbenzoic acid

(+)-α-pinene
7785-70-8

(+)-α-pinene

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
at 140℃;
2-Benzoylbenzoic acid
85-52-9

2-Benzoylbenzoic acid

(1R,5R)-(+)-β-pinene
127-91-3

(1R,5R)-(+)-β-pinene

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
at 140℃;
(R)-(+)-binaphthol mononeryl ether
86851-45-8

(R)-(+)-binaphthol mononeryl ether

A

Terpinolene
586-62-9

Terpinolene

B

D-limonene
5989-27-5

D-limonene

C

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; tri-tert-butylphenol; diisobutylaluminium hydride 2.) 3 h, -130 deg C, CCl3F; Yield given. Multistep reaction. Yields of byproduct given;
(R)-(+)-binaphthol mononeryl ether
86851-45-8

(R)-(+)-binaphthol mononeryl ether

A

D-limonene
5989-27-5

D-limonene

B

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
With (2,4,6-tri-tert-butylphenoxy)-isobutylaluminium trifluormethanesulfonate In trichlorofluoromethane at -130℃; for 3h; further reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(-)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]ethyl}benzene
130814-75-4

(-)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]ethyl}benzene

isoprene
78-79-5

isoprene

A

D-limonene
5989-27-5

D-limonene

B

(-)-trans-carveol
18383-51-2

(-)-trans-carveol

C

(+)-trans-carveol
2102-58-1

(+)-trans-carveol

D

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
at 50℃; under 135011 Torr; for 60h; Product distribution; other conditions; other 1-(1-arylalkoxy)-2-methyl-1,3-butadienes; enantioselectivity of the reaction;
[(S)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene
136476-14-7

[(S)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene

isoprene
78-79-5

isoprene

A

D-limonene
5989-27-5

D-limonene

B

(-)-trans-carveol
18383-51-2

(-)-trans-carveol

C

(+)-trans-carveol
2102-58-1

(+)-trans-carveol

D

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
at 50℃; under 135011 Torr; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
[(R)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene
175522-76-6

[(R)-2,2-Dimethyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene

isoprene
78-79-5

isoprene

A

D-limonene
5989-27-5

D-limonene

B

(-)-trans-carveol
18383-51-2

(-)-trans-carveol

C

(+)-trans-carveol
2102-58-1

(+)-trans-carveol

D

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
at 50℃; under 135011 Torr; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
[(S)-2-Methyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene
136476-12-5

[(S)-2-Methyl-1-((E)-2-methyl-buta-1,3-dienyloxy)-propyl]-benzene

isoprene
78-79-5

isoprene

A

D-limonene
5989-27-5

D-limonene

B

(-)-trans-carveol
18383-51-2

(-)-trans-carveol

C

(+)-trans-carveol
2102-58-1

(+)-trans-carveol

D

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
at 50℃; under 135011 Torr; for 60h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Benzyl-methyl-[2-((R)-4-methyl-cyclohex-3-enyl)-propyl]-amine

Benzyl-methyl-[2-((R)-4-methyl-cyclohex-3-enyl)-propyl]-amine

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
With dihydrogen peroxide In tert-butyl alcohol 1.) 25 deg C, 110 h, 2.) 150 deg C, 1 torr, 1 h; Yield given;
methanol
67-56-1

methanol

(1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane
5718-75-2

(1R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane

Raney nickel

Raney nickel

A

trans-1,4-menthane
1678-82-6

trans-1,4-menthane

B

cis-1-isopropyl-4-methyl-cyclohexane
6069-98-3

cis-1-isopropyl-4-methyl-cyclohexane

C

D-limonene
5989-27-5

D-limonene

D

(+)-p-menth-1-ene
1195-31-9

(+)-p-menth-1-ene

linalool
126-91-0

linalool

Japanese acid earth

Japanese acid earth

A

7-methyl-3-methene-1,6-octadiene
123-35-3

7-methyl-3-methene-1,6-octadiene

B

Geraniol
106-24-1

Geraniol

C

terpineol
98-55-5

terpineol

D

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
at 159℃;
formic acid
64-18-6

formic acid

A

Terpinolene
586-62-9

Terpinolene

B

D-limonene
5989-27-5

D-limonene

C

limonene.
138-86-3

limonene.

D

terpinene

terpinene

Conditions
ConditionsYield
d-α-pinene;
diethyl ether
60-29-7

diethyl ether

1,2,8,9-tetrabromo-p-menthane
4764-54-9

1,2,8,9-tetrabromo-p-menthane

iodine
7553-56-2

iodine

magnesium

magnesium

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
at 0℃; d-limonene tetrabromide;
ethanol
64-17-5

ethanol

1,2,8,9-tetrabromo-p-menthane
4764-54-9

1,2,8,9-tetrabromo-p-menthane

zinc dust

zinc dust

D-limonene
5989-27-5

D-limonene

Conditions
ConditionsYield
d-limonene tetrabromide;
(+)-α-pinene
7785-70-8

(+)-α-pinene

aluminium silicate

aluminium silicate

A

D-limonene
5989-27-5

D-limonene

B

(+)-camphene
79-92-5

(+)-camphene

Conditions
ConditionsYield
Mechanism;
(+)-α-pinene
7785-70-8

(+)-α-pinene

titanic acid

titanic acid

A

D-limonene
5989-27-5

D-limonene

B

(+)-camphene
79-92-5

(+)-camphene

Conditions
ConditionsYield
Mechanism;
(+)-α-pinene
7785-70-8

(+)-α-pinene

acetic acid
64-19-7

acetic acid

fired clay

fired clay

A

terpineol
98-55-5

terpineol

B

D-limonene
5989-27-5

D-limonene

rac-endo-borneol
6627-72-1

rac-endo-borneol

D

1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
507-70-0

1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol

Conditions
ConditionsYield
at 30℃; anschl. Verseifen;
(+)-α-pinene
7785-70-8

(+)-α-pinene

fired clay

fired clay

A

D-limonene
5989-27-5

D-limonene

B

(+)-camphene
79-92-5

(+)-camphene

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
at 10℃;
(1S)-endo-fenchylamine
131348-01-1

(1S)-endo-fenchylamine

acetic acid
64-19-7

acetic acid

sodium nitrite

sodium nitrite

A

D-limonene
5989-27-5

D-limonene

B

α-fenchene
116724-26-6

α-fenchene

C

(+)-cyclofenchene
488-97-1

(+)-cyclofenchene

D

(-)-ξ-fenchene

(-)-ξ-fenchene

Conditions
ConditionsYield
Produkt 5: (+)-α-Terpineol, Produkt 6: (-)-α-Fenchol, Produkt 7: (-)-β-Fenchol und Produkt 8: (-)-α-Fenchenhydrat;
phthalic acid mono-((R)-p-menth-1-en-8-yl ester)

phthalic acid mono-((R)-p-menth-1-en-8-yl ester)

aqueous NaOH-solution

aqueous NaOH-solution

A

D-limonene
5989-27-5

D-limonene

B

d-α-terpineol

d-α-terpineol

Conditions
ConditionsYield
bei der Wasserdampfdestillation;
α-terpinyl chloride
39864-10-3

α-terpinyl chloride

A

Terpinolene
586-62-9

Terpinolene

B

D-limonene
5989-27-5

D-limonene

C

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine for 8h; Heating; Title compound not separated from byproducts;
2-Benzyloxy-2'-((Z)-3,7-dimethyl-octa-2,6-dienyloxy)-[1,1']binaphthalenyl

2-Benzyloxy-2'-((Z)-3,7-dimethyl-octa-2,6-dienyloxy)-[1,1']binaphthalenyl

A

1-methyl-4-isopropyl-1,3-cyclohexadiene
99-86-5

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

B

α-terpinyl chloride
39864-10-3

α-terpinyl chloride

C

D-limonene
5989-27-5

D-limonene

D

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
With tin(IV) chloride In various solvent(s) at -78℃; for 12h; Product distribution; Further Variations:; Solvents; Reagents; Temperatures; time;
2'-((Z)-3,7-Dimethyl-octa-2,6-dienyloxy)-2-(4-trifluoromethyl-benzyloxy)-[1,1']binaphthalenyl

2'-((Z)-3,7-Dimethyl-octa-2,6-dienyloxy)-2-(4-trifluoromethyl-benzyloxy)-[1,1']binaphthalenyl

A

α-terpinyl chloride
39864-10-3

α-terpinyl chloride

B

D-limonene
5989-27-5

D-limonene

C

(-)-(S)-limonene
5989-54-8

(-)-(S)-limonene

Conditions
ConditionsYield
With tin(ll) chloride In dichloromethane at -97℃; for 6h; Product distribution; Further Variations:; Solvents; Temperatures; time;
D-limonene
5989-27-5

D-limonene

(+)-p-menth-1-ene
1195-31-9

(+)-p-menth-1-ene

Conditions
ConditionsYield
With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; under 7500.75 Torr; for 20h; Inert atmosphere; Sealed tube;100%
With ethanol; lithium; nickel dichloride; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 20℃; for 22h;99%
With platinum(IV) oxide; hydrogen under 775.743 Torr; regioselective reaction;99%
D-limonene
5989-27-5

D-limonene

(4R)-limonene 1,2-epoxide
1195-92-2

(4R)-limonene 1,2-epoxide

Conditions
ConditionsYield
With urea hydrogen peroxide adduct; methyltrioxorhenium(VII) In dichloromethane at 20℃; for 0.5h;99%
With tert.-butylhydroperoxide In decane at 55℃; for 3h; in air; regioselective reaction;95%
With C15H34N(1+)*H2O4P(1-); Tri(dodecyltrimethylammonium) dodecatungstophosphate; dihydrogen peroxide In water; toluene at 65℃; for 6h; Inert atmosphere;95%
D-limonene
5989-27-5

D-limonene

C37H48N2O4S3

C37H48N2O4S3

C47H64N2O4S3

C47H64N2O4S3

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In toluene at 20℃; for 36h; Sealed tube; Irradiation; Inert atmosphere;99%
D-limonene
5989-27-5

D-limonene

cis-(R)-limonene oxide
4680-24-4

cis-(R)-limonene oxide

Conditions
ConditionsYield
With dihydrogen peroxide; polystyrene; {2-(aminomethyl)pyridine}methyl(trioxo)rhenium(VII) In dichloromethane; water; acetonitrile at -10℃; for 2h;98%
With dihydrogen peroxide; divinylbenzene cross-linked poly(4-vinylpyridine); methyltrioxorhenium(VII) In dichloromethane; water; acetonitrile at 25℃; for 1.5h;89%
Multi-step reaction with 2 steps
1: bis[(4R)-2(4-Et-3,4-dihydro-2-oxazolyl)phenolato-N,O]O(O2)Mo; aq. tert-butyl hydroperoxide / toluene / 22 h / 20 °C
2: (μ-O)[MoO2(NCS)-2-(3,4-dihydro-4-MeOMe-oxazolyl-Ph)Py-N,N]2; aq. tert-butyl hydroperoxide / toluene / 22 h / 20 °C
View Scheme
D-limonene
5989-27-5

D-limonene

(R)-5-Isopropenyl-2-methylene-cyclohexyl-hydroperoxide

(R)-5-Isopropenyl-2-methylene-cyclohexyl-hydroperoxide

Conditions
ConditionsYield
With zeolite NaY; oxygen Irradiation; photooxygenation;97%
D-limonene
5989-27-5

D-limonene

diphenylsilane
775-12-2

diphenylsilane

(2-((R)-4-methylcyclohex-3-en-1-yl)propyl)diphenylsilane

(2-((R)-4-methylcyclohex-3-en-1-yl)propyl)diphenylsilane

Conditions
ConditionsYield
Stage #1: diphenylsilane With [(2-dicyclohexylphosphinocyclopentene-1-(2,6-dimethylphenyl)imine)Ni(allyl)]OTf In benzene-d6 at 20℃; for 0.0833333h; Inert atmosphere; Glovebox;
Stage #2: D-limonene In benzene-d6 at 20℃; for 12h; Inert atmosphere; Sealed tube;
97%
With [N,N'-(1,2-dimethyl-1,2-ethanediylidene)bis[3-(diphenylphosphino)-1-propanamine]]Ni In benzene-d6 at 70℃; for 168h; Inert atmosphere;76%
D-limonene
5989-27-5

D-limonene

phenylsilane
694-53-1

phenylsilane

(4R)-1-methyl-4-[(1R,S)-1-methyl-2-(phenylsilyl)ethyl]cyclohex-1-ene

(4R)-1-methyl-4-[(1R,S)-1-methyl-2-(phenylsilyl)ethyl]cyclohex-1-ene

Conditions
ConditionsYield
With n-butyllithium; 2,6-bis-[1-(2,6-diethylphenylimino)ethyl]pyridine iron(II) chloride In hexane; toluene at 20℃; for 1h; Inert atmosphere; regioselective reaction;96%
Stage #1: phenylsilane With (C5Me5)(iPr2MeP)H2FeH(N2); trityl tetrakis(pentafluorophenyl)borate In fluorobenzene at -35 - 20℃;
Stage #2: D-limonene In fluorobenzene at 20℃; for 20h; regioselective reaction;
92%
yttrium(pentamethylcyclopentadienyl)2CH(trimethylsilyl)2 In benzene for 96h; Ambient temperature;61%
(η5-C5Me4(i)Pr)2YMe*THF for 96h; Product distribution; Ambient temperature; other catalysts;
With [(2,6-iPr2PhBDI)Mn(μ-H)]2 In benzene-d6 at 130℃; for 144h; Inert atmosphere;
D-limonene
5989-27-5

D-limonene

A

(R)-8,9-limonene oxide
184488-93-5

(R)-8,9-limonene oxide

(1RS,2SR,4R)-limonene-1,2-epoxide
203719-54-4

(1RS,2SR,4R)-limonene-1,2-epoxide

Conditions
ConditionsYield
With 1H-imidazole; dihydrogen peroxide; sodium N-dodecanoyl-L-proplinate; Mn[5-(4-C6H4CO-(N-L-proline))-10,15,20-Ph3-porphyrinyl]Cl In ethanol; water at 25℃; for 0.166667h; Product distribution; Further Variations:; Catalysts; Reagents;A n/a
B 95%
D-limonene
5989-27-5

D-limonene

1-Chloro-4-(1-chloro-1-methyl-ethyl)-1-methyl-cyclohexane
4497-96-5

1-Chloro-4-(1-chloro-1-methyl-ethyl)-1-methyl-cyclohexane

Conditions
ConditionsYield
With acetyl chloride In ethanol at 30℃; for 0.166667h; Markovnikov hydrochlorination;95%
Multi-step reaction with 2 steps
1: 250 - 270 °C
2: diethyl ether; hydrogen chloride
View Scheme
D-limonene
5989-27-5

D-limonene

A

trans-1,4-menthane
1678-82-6

trans-1,4-menthane

B

cis-1-isopropyl-4-methyl-cyclohexane
6069-98-3

cis-1-isopropyl-4-methyl-cyclohexane

C

(+)-p-menth-1-ene
1195-31-9

(+)-p-menth-1-ene

Conditions
ConditionsYield
With hydrogen; 2 In neat (no solvent)A 2%
B 4%
C 94%
With ruthenium; hydrogen at 30℃; under 900.09 Torr; Reagent/catalyst;
morpholine
110-91-8

morpholine

carbon monoxide
201230-82-2

carbon monoxide

D-limonene
5989-27-5

D-limonene

4-[3-((R)-4-Methyl-cyclohex-3-enyl)-butyl]-morpholine

4-[3-((R)-4-Methyl-cyclohex-3-enyl)-butyl]-morpholine

Conditions
ConditionsYield
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer In acetonitrile at 80℃; under 60004.8 Torr; for 20h;93%
Stage #1: morpholine; carbon monoxide; D-limonene With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In tetrahydrofuran at 100℃; Autoclave;
Stage #2: With hydrogen In tetrahydrofuran at 100℃; under 30003 Torr; Autoclave;
79%
D-limonene
5989-27-5

D-limonene

(1S,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol
59121-74-3

(1S,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Conditions
ConditionsYield
With oxygen; potassium carbonate In water at 25℃; under 1551.49 Torr; for 72h; enantioselective reaction;92%
D-limonene
5989-27-5

D-limonene

2-bromo-1-hydroxy-p-menth-8-ene
506422-90-8

2-bromo-1-hydroxy-p-menth-8-ene

Conditions
ConditionsYield
With N-Bromosuccinimide In water; acetone at 10℃;91%
D-limonene
5989-27-5

D-limonene

(1S,4R)-2-chloro-4-(1-methylvinyl)-1-methylcyclohexanol
521925-06-4

(1S,4R)-2-chloro-4-(1-methylvinyl)-1-methylcyclohexanol

Conditions
ConditionsYield
With sodium hypochlorite; water; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 60℃; for 9h; Temperature; Solvent;90.2%
D-limonene
5989-27-5

D-limonene

p-menth-1-ene
61585-35-1

p-menth-1-ene

Conditions
ConditionsYield
With hydrogen; platinum on activated charcoal pressure of 60 lb/sq in. to 43.5 lb/sq in.;90%
With copper at 200℃; inactive substances;
With hydrogen; platinum dihydrolimonene;
With sodium tetrahydroborate In methanol at 20℃; Catalytic behavior; Reagent/catalyst; Inert atmosphere;
D-limonene
5989-27-5

D-limonene

4-isopropenyl-1-methylcyclohexane
6252-33-1

4-isopropenyl-1-methylcyclohexane

Conditions
ConditionsYield
Stage #1: D-limonene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 25℃; for 2.5h; Inert atmosphere;
Stage #2: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 760.051 Torr; Inert atmosphere;
Stage #3: With 2-methyl-2-nitrosopropane dimer In tetrahydrofuran for 0.75h; regioselective reaction;
90%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

D-limonene
5989-27-5

D-limonene

A

(Ξ)-3-((R)-4-methyl-cyclohex-3-enyl)-butyraldehyde diethylacetal

(Ξ)-3-((R)-4-methyl-cyclohex-3-enyl)-butyraldehyde diethylacetal

B

3-(4-methylcyclohex-3-enyl)butanal
199445-85-7

3-(4-methylcyclohex-3-enyl)butanal

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; tri(o-t-butylphenyl)phosphite; hydrogen at 80℃; under 60804.1 Torr; for 4h; Inert atmosphere; Autoclave;A 90%
B n/a
D-limonene
5989-27-5

D-limonene

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol
287720-47-2

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol

Conditions
ConditionsYield
Stage #1: D-limonene With PS-9-BBN In tetrahydrofuran at 40℃; for 24h;
Stage #2: With tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide In tetrahydrofuran; methanol at 0 - 50℃; for 4h;
89%
Stage #1: D-limonene With 9-bora-bicyclo[3.3.1]nonane at 20℃; Inert atmosphere;
Stage #2: With dihydrogen peroxide; sodium hydroxide In ethanol at 50℃; for 2h;
89.6%
Stage #1: D-limonene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 20℃; for 2h;
Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; water temp. < 10 deg C;
Stage #3: In tetrahydrofuran; water at 40℃; for 2h;
80%
D-limonene
5989-27-5

D-limonene

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon at 140℃; for 1h;89%
With iodine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 0.75h; Reflux;82%
With dodecane; hydrogen at 300℃; under 11251.1 Torr; for 2h; Catalytic behavior; Temperature; Autoclave; Inert atmosphere;57%
piperazine
110-85-0

piperazine

carbon monoxide
201230-82-2

carbon monoxide

D-limonene
5989-27-5

D-limonene

C15H28N2
1098145-03-9

C15H28N2

Conditions
ConditionsYield
Stage #1: piperazine; carbon monoxide; D-limonene With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In tetrahydrofuran at 100℃; Autoclave;
Stage #2: With hydrogen In tetrahydrofuran at 100℃; under 30003 Torr; Autoclave;
89%
D-limonene
5989-27-5

D-limonene

(1S,2S,4R)-2-bromo-1-methyl-4-(prop-1-en-2-yl)cyclohexanol

(1S,2S,4R)-2-bromo-1-methyl-4-(prop-1-en-2-yl)cyclohexanol

Conditions
ConditionsYield
With sodium hypobromide; copper(II) acetate monohydrate In water; 1,2-dichloro-ethane at 80℃; for 6h; Reagent/catalyst; Temperature;88.3%
With N-Bromosuccinimide; water In acetone at 0 - 5℃;85%
With N-Bromosuccinimide; water In acetone at 0 - 25℃; for 1h; Large scale; chemoselective reaction;
With N-Bromosuccinimide In water; acetone at 0 - 25℃; for 1h;
With N-Bromosuccinimide In water; acetone at 0℃; for 0.666667h; Inert atmosphere; Schlenk technique; Glovebox;
Conditions
ConditionsYield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; cetyltrimethylammonim bromide In dichloromethane; chloroform87%
D-limonene
5989-27-5

D-limonene

(R)-4-methyl-3-(3'-oxobutyl)pent-4-enal
7086-79-5, 85031-77-2, 127288-10-2, 136521-14-7

(R)-4-methyl-3-(3'-oxobutyl)pent-4-enal

Conditions
ConditionsYield
Stage #1: D-limonene With pyridine; ozone In methanol at -50℃; for 12h; Inert atmosphere;
Stage #2: With dimethylsulfide In methanol at -50℃;
86%
Stage #1: D-limonene With oxygen; ozone In methanol; dichloromethane at -70℃;
Stage #2: With dimethylsulfide at 20℃; for 5h;
70%
Stage #1: D-limonene With ozone In methanol; dichloromethane at -70℃;
Stage #2: With dimethylsulfide In methanol; dichloromethane at 20℃; for 5h;
70%
D-limonene
5989-27-5

D-limonene

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

(1'R,2RS)-2-methyl-2-(4'-methylcyclohex-3'-enyl)-2,3,5,6,7-pentahydrobenzo[1,2-b]furan-4-one

(1'R,2RS)-2-methyl-2-(4'-methylcyclohex-3'-enyl)-2,3,5,6,7-pentahydrobenzo[1,2-b]furan-4-one

Conditions
ConditionsYield
With manganese triacetate; acetic acid at 70℃; for 2h;86%
D-limonene
5989-27-5

D-limonene

acetylacetone
123-54-6

acetylacetone

(1'R,5RS)-3-acetyl-2,5-dimethyl-5-(4'-methylcyclohex-3'-enyl)-4,5-dihydrofuran

(1'R,5RS)-3-acetyl-2,5-dimethyl-5-(4'-methylcyclohex-3'-enyl)-4,5-dihydrofuran

Conditions
ConditionsYield
With manganese triacetate; acetic acid at 70℃; for 1.5h;86%
D-limonene
5989-27-5

D-limonene

1-phenylbutan-1,3-dione
93-91-4

1-phenylbutan-1,3-dione

[2,5-Dimethyl-5-((R)-4-methyl-cyclohex-3-enyl)-4,5-dihydro-furan-3-yl]-phenyl-methanone

[2,5-Dimethyl-5-((R)-4-methyl-cyclohex-3-enyl)-4,5-dihydro-furan-3-yl]-phenyl-methanone

Conditions
ConditionsYield
With manganese triacetate; acetic acid at 70℃; for 1.5h;86%
Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen at 20℃; under 760.051 Torr; Overall yield = 16 g;A n/a
B 85%
With (bis-1,2-diphenylphosphinoethane)Co(CH2SiMe3)2; hydrogen In benzene at 25℃; under 3040.2 Torr; for 6h; Time;A 55%
B 42%
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; below 20 deg C; Yield given. Yields of byproduct given;
With platinum(IV) oxide; hydrogen In ethanol at 20℃; under 760.051 Torr; for 5.4h;
D-limonene
5989-27-5

D-limonene

(R)-8,9-limonene oxide
184488-93-5

(R)-8,9-limonene oxide

Conditions
ConditionsYield
With perchloric acid; dihydrogen peroxide In water; acetonitrile; tert-butyl alcohol at 60℃; for 0.166667h; stereoselective reaction;85%
With fluorapatite; dihydrogen peroxide; tris(cetylpyridinium) 12-tungstophosphate In water at 25℃; for 14h;61%
With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 24h;35%
D-limonene
5989-27-5

D-limonene

O,O-diisopropyl hydrogen phosphorodithioate
107-56-2

O,O-diisopropyl hydrogen phosphorodithioate

O,O-diisopropyl S-[1-methyl-1-(4-methylcyclohex-3-en-1-yl)ethyl]dithiophosphate

O,O-diisopropyl S-[1-methyl-1-(4-methylcyclohex-3-en-1-yl)ethyl]dithiophosphate

Conditions
ConditionsYield
With zinc(II) chloride at 20℃; for 2h;85%
With zinc(II) chloride at 20℃; Inert atmosphere;85%
With zinc(II) chloride
propylamine
107-10-8

propylamine

carbon monoxide
201230-82-2

carbon monoxide

D-limonene
5989-27-5

D-limonene

C14H27N
1098144-84-3

C14H27N

Conditions
ConditionsYield
Stage #1: propylamine; carbon monoxide; D-limonene With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen In tetrahydrofuran at 100℃; Autoclave;
Stage #2: With hydrogen In tetrahydrofuran at 100℃; under 30003 Torr; Autoclave;
85%

5989-27-5Relevant articles and documents

Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors

Kutateladze, Dennis A.,Strassfeld, Daniel A.,Jacobsen, Eric N.

, p. 6951 - 6956 (2020/05/19)

Chiral urea derivatives are shown to catalyze enantioselective tail-to-head cyclization reactions of neryl chloride analogues. Experimental data are consistent with a mechanism in which ?-participation by the nucleophilic olefin facilitates chloride ionization and thereby circumvents simple elimination pathways. Kinetic and computational studies support a cooperative mode of catalysis wherein two molecules of the urea catalyst engage the substrate and induce enantioselectivity through selective transition state stabilization.

Upcycling a plastic cup: One-pot synthesis of lactate containing metal organic frameworks from polylactic acid

Slater, Benjamin,Wong, So-On,Duckworth, Andrew,White, Andrew J. P.,Hill, Matthew R.,Ladewig, Bradley P.

supporting information, p. 7319 - 7322 (2019/06/27)

Waste PLA can be upcycled to metal organic frameworks of potential high value in a one-pot synthesis scheme, where PLA depolymerisation occurs in situ. Three homochiral lactate based frameworks were successfully synthesised and characterised from PLA as a feed source, including ZnBLD. The chiral separation ability of ZnBLD was maintained.

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

Takada, Yuki,Caner, Joaquim,Kaliyamoorthy, Selvam,Naka, Hiroshi,Saito, Susumu

supporting information, p. 18025 - 18032 (2017/12/08)

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.

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