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(1R)-(+)-alpha-Pinene Manufacturer/High quality/Best price/In stock
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(1R)-(+)-ALPHA-PINENE
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99% (1R)-(+)-alpha-Pinene ManufacturerIn stock CAS NO.7785-70-8
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7785-70-8 Usage

Chemical Properties

(1R)-(+)-ALPHA-PINENE is Clear colourless liquid

Uses

(1R)-(+)-α-Pinene is used in hydroboration reactions and the reduction of ketones.

Uses

(+)-alpha-Pinene is employed in the preparation of chiral hydroboration reagents. It is a bronchodilator in humans. α-Pinene is an anti-inflammatory and used as a broad-spectrum antibiotic.It exhibits activity as an acetylcholinesterase inhibitor, aiding memory. It is a biosynthetic base for CB2 ligands, such as HU-308.

Uses

(+)-α-Pinene has been used in a tolerance testing procedure to detect the genes in Marinobacter aquaeolei, for engineering a pinene tolerant Escherichia coli.

Definition

ChEBI: The (+)-enantiomer of alpha-pinene.

General Description

(+)-α-Pinene is a monoterpenoid compound mainly found in Pinus species.

Purification Methods

(1R)-(+)-ALPHA-PINENE is isomerised by heat, acids and certain solvents. It should be distilled under reduced pressure under nitrogen and stored in the dark. It has been purified via the nitrosochloride [Waterman et al. Recl Trav Chim, Pays-Bas 48 1191 1929]. For purification of optically active forms see Lynn [J Am Chem Soc 91 361 1919].
InChI:InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8H,4-6H2,1-3H3

7785-70-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (P1099)  (1R)-(+)-α-Pinene  >97.0%(GC) 7785-70-8 25mL 225.00CNY Detail
TCI America (P1099)  (1R)-(+)-α-Pinene  >97.0%(GC) 7785-70-8 100mL 540.00CNY Detail
TCI America (P1099)  (1R)-(+)-α-Pinene  >97.0%(GC) 7785-70-8 500mL 1,610.00CNY Detail
Alfa Aesar (L04941)  (+)-alpha-Pinene, 98%    7785-70-8 50g 330.0CNY Detail
Alfa Aesar (L04941)  (+)-alpha-Pinene, 98%    7785-70-8 250g 1041.0CNY Detail
Sigma-Aldrich (80605)  (+)-α-Pinene  analytical standard 7785-70-8 80605-1ML 424.71CNY Detail
Sigma-Aldrich (80605)  (+)-α-Pinene  analytical standard 7785-70-8 80605-5ML 1,738.62CNY Detail
Aldrich (268070)  (+)-α-Pinene  ≥99% 7785-70-8 268070-5G 532.35CNY Detail
Aldrich (268070)  (+)-α-Pinene  ≥99% 7785-70-8 268070-25G 1,831.05CNY Detail
Aldrich (P45680)  (+)-α-Pinene  98% 7785-70-8 P45680-100ML 614.25CNY Detail
Aldrich (P45680)  (+)-α-Pinene  98% 7785-70-8 P45680-500ML 2,378.61CNY Detail

7785-70-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 9, 2017

Revision Date: Aug 9, 2017

1.Identification

1.1 GHS Product identifier

Product name (+)-α-pinene

1.2 Other means of identification

Product number -
Other names (1R,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-ene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:7785-70-8 SDS

7785-70-8Synthetic route

C30H45BO

C30H45BO

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-1-Phenyl-3-buten-1-ol
77118-87-7

(S)-1-Phenyl-3-buten-1-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; isobutyraldehyde at 65℃; for 12h;A 90%
B 90%
diisopinocampheylborane
21932-54-7

diisopinocampheylborane

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
Stage #1: With benzaldehyde at 50℃; Oxidation;
Stage #2: diisopinocampheylborane With boron trifluoride diethyl etherate at 100℃; for 1h; Oxidation;
86%
C28H47BO

C28H47BO

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1R,1'R)-(+)-1-(2-cyclohexenyl)-1-ethanol
95674-80-9

(1R,1'R)-(+)-1-(2-cyclohexenyl)-1-ethanol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; isobutyraldehyde at 65℃; for 12h;A 84%
B 67%
diisopinocampheylborane

diisopinocampheylborane

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
Stage #1: diisopinocampheylborane With benzaldehyde Inert atmosphere; Cooling with ice;
Stage #2: With boron trifluoride diethyl etherate at 100℃; for 1h; Inert atmosphere;
71%
(1S,4R,5R)-3-iodo-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene
911673-20-6

(1S,4R,5R)-3-iodo-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
473-62-1

(1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

C

6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene
190715-28-7

6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
Stage #1: (1S,4R,5R)-3-iodo-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene With potassium tert-butylate In diethylene glycol dimethyl ether at 170℃; for 8h;
Stage #2: With silica gel In hexane
A 6%
B 32%
C 54%
(-)-isopinocamphyl tosylate
62697-75-0

(-)-isopinocamphyl tosylate

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene
24031-98-9

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110℃; for 3h; Title compound not separated from byproducts.;A 45%
B 45%
(-)-isopinocampheol
1196-00-5

(-)-isopinocampheol

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(+)-pinocamphyl chloride
185378-26-1

(+)-pinocamphyl chloride

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine for 16h; Heating;A n/a
B 30%

A

(-)-α-pinene
7785-26-4

(-)-α-pinene

B

(+)-α-pinene
7785-70-8

(+)-α-pinene

C

2,4,4-Trimethyl-8-methylene-3-aza-bicyclo[3.3.1]non-2-ene

2,4,4-Trimethyl-8-methylene-3-aza-bicyclo[3.3.1]non-2-ene

Conditions
ConditionsYield
With chloranil In dichloromethane; acetonitrile Irradiation; Yield given;A n/a
B n/a
C 5%
ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(-)-trans-δ-pinene
24031-99-0

(-)-trans-δ-pinene

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene
24031-98-9

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene

rac-α-pinene
80-56-8

rac-α-pinene

A

(-)-α-pinene
7785-26-4

(-)-α-pinene

B

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
Leiten des Dampfes durch Gelatine-Hydrosol;
(+)-pinocamphone-hydrazone

(+)-pinocamphone-hydrazone

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(-)-trans-δ-pinene
24031-99-0

(-)-trans-δ-pinene

Conditions
ConditionsYield
With ethanol; mercury(II) oxide
Conditions
ConditionsYield
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) toluene, -50 deg C, 1h, 2.) toluene, 26 deg C, 10h; Yield given. Multistep reaction. Yields of byproduct given;
cyclopinene
73956-74-8

cyclopinene

A

Beta-pinene
177698-19-0

Beta-pinene

B

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

C

camphene
79-92-5

camphene

D

2-menthene
5256-65-5

2-menthene

E

(+)-α-pinene
7785-70-8

(+)-α-pinene

F

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With KU 21 cation-exchange resin In hexane at 70℃; for 1h; Product distribution;A 4 % Chromat.
B n/a
C 3 % Chromat.
D n/a
E 76 % Chromat.
F n/a

A

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

B

(+)-α-pinene
7785-70-8

(+)-α-pinene

C

cyclopinene
73956-74-8

cyclopinene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 5h; Heating; Yield given. Yields of byproduct given;
benzaldehyde
100-52-7

benzaldehyde

(4aR,8aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-benzo[b]borinine
175656-35-6

(4aR,8aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-benzo[b]borinine

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,8aR)-1-Benzyloxy-decahydro-benzo[b]borinine
878381-35-2

(4aR,8aR)-1-Benzyloxy-decahydro-benzo[b]borinine

Conditions
ConditionsYield
In diethyl ether at 0℃; for 6h; Elimination;
benzaldehyde
100-52-7

benzaldehyde

(4aR,9aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-1-bora-benzocycloheptene

(4aR,9aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-1-bora-benzocycloheptene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,9aR)-1-Benzyloxy-decahydro-1-bora-benzocycloheptene

(4aR,9aR)-1-Benzyloxy-decahydro-1-bora-benzocycloheptene

Conditions
ConditionsYield
In diethyl ether at 0℃; Elimination;
benzaldehyde
100-52-7

benzaldehyde

(4aR,10aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-dodecahydro-1-bora-benzocyclooctene

(4aR,10aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-dodecahydro-1-bora-benzocyclooctene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,10aR)-1-Benzyloxy-dodecahydro-1-bora-benzocyclooctene

(4aR,10aR)-1-Benzyloxy-dodecahydro-1-bora-benzocyclooctene

Conditions
ConditionsYield
In diethyl ether at 0℃; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(R)-2-Ethyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(R)-2-Ethyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(R)-1-Ethoxy-2-ethyl-borolane

(R)-1-Ethoxy-2-ethyl-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(S)-2-Isopropyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(S)-2-Isopropyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-1-Ethoxy-2-isopropyl-borolane

(S)-1-Ethoxy-2-isopropyl-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(S)-2-(2,2-Dimethyl-propyl)-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(S)-2-(2,2-Dimethyl-propyl)-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-2-(2,2-Dimethyl-propyl)-1-ethoxy-borolane

(S)-2-(2,2-Dimethyl-propyl)-1-ethoxy-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(3aR,7aR)-4-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-octahydro-4-bora-indene

(3aR,7aR)-4-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-octahydro-4-bora-indene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(3aR,7aR)-4-Ethoxy-octahydro-4-bora-indene

(3aR,7aR)-4-Ethoxy-octahydro-4-bora-indene

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(S)-2-Benzyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(S)-2-Benzyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-2-Benzyl-1-ethoxy-borolane

(S)-2-Benzyl-1-ethoxy-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(4aR,8aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-benzo[b]borinine
175656-35-6

(4aR,8aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-benzo[b]borinine

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,8aR)-1-Ethoxy-decahydro-benzo[b]borinine
217079-79-3

(4aR,8aR)-1-Ethoxy-decahydro-benzo[b]borinine

Conditions
ConditionsYield
In diethyl ether at 0℃; for 1h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(S)-2-Cyclopentylmethyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(S)-2-Cyclopentylmethyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-2-Cyclopentylmethyl-1-ethoxy-borolane

(S)-2-Cyclopentylmethyl-1-ethoxy-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
2,3-epoxy-cis-pinane
14575-92-9

2,3-epoxy-cis-pinane

benzene
71-43-2

benzene

sodium

sodium

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(+)-pinocamphone
18492-59-6

(+)-pinocamphone

C

(-)-trans-pinocarveol
1674-08-4

(-)-trans-pinocarveol

d-pinene nitrosochloride

d-pinene nitrosochloride

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
With ethanol; aniline
l-pinene nitrosochloride

l-pinene nitrosochloride

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
With ethanol; aniline
(-)(1R)-3ξ-chloro-cis-pinane
117227-80-2

(-)(1R)-3ξ-chloro-cis-pinane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(+)-δ-pinene

(+)-δ-pinene

Conditions
ConditionsYield
With potassium phenolate at 150℃;
(+)-α-pinene
7785-70-8

(+)-α-pinene

2-Pinene oxide
217320-94-0

2-Pinene oxide

Conditions
ConditionsYield
With 4-tert-butylpyridine; urea hydrogen peroxide adduct; methyltrioxorhenium(VII) In nitromethane; water at 0℃; for 5h;100%
With dihydrogen peroxide; sodium acetate; acetic anhydride; sodium hydrogencarbonate In 1,2-dichloro-ethane at 50℃; for 4h; Solvent; Reagent/catalyst; Temperature;90%
With Candida antarctica lipase B; Octanoic acid; choline chloride; dihydrogen peroxide; glycerol; urea In water at 60℃; for 3h; Reagent/catalyst; Solvent; Time; Temperature;84.6%
(+)-α-pinene
7785-70-8

(+)-α-pinene

diisopinocampheylborane
21932-54-7

diisopinocampheylborane

Conditions
ConditionsYield
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane at 0 - 20℃; hydroboration;99%
With dimethylsulfide borane complex In tetrahydrofuran; dimethyl sulfoxide at 0 - 20℃; Inert atmosphere;90%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 24h;85%
(+)-α-pinene
7785-70-8

(+)-α-pinene

(1S)-pinocarvone
19890-00-7

(1S)-pinocarvone

Conditions
ConditionsYield
With oxygen; 5,15,10,20-tetraphenylporphyrin; acetic anhydride; dmap In dichloromethane at 20℃; for 18h; Irradiation;99%
With tetraphenyl pyrophosphate; oxygen; acetic anhydride Irradiation;99%
With pyridine; dmap; 5,10,15,20-tetrakisphenylporphyrin; oxygen; acetic anhydride In dichloromethane for 1.5h; Irradiation;97%
(+)-α-pinene
7785-70-8

(+)-α-pinene

2,3-epoxy-cis-pinane
14575-92-9

2,3-epoxy-cis-pinane

Conditions
ConditionsYield
With dihydrogen peroxide; (trans-1,2-diaminocyclohexane)methyltrioxorhenium In dichloromethane; water; acetonitrile at -10℃; for 1h;98%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;93%
With 3,3-dimethyldioxirane In dichloromethane; acetone at -5 - 0℃; for 2h;92%
(+)-α-pinene
7785-70-8

(+)-α-pinene

/PMIBI134-1530/

/PMIBI134-1530/

R-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane
73624-47-2, 76695-88-0, 100347-98-6, 64106-79-2

R-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane

Conditions
ConditionsYield
In tetrahydrofuran at 24℃; for 24h; Product distribution; other time; hydroboration of 2-organylapopinenes with 9-borabicyclo<3.3.1>nonane; effect of steric factors of alkyl substituent on the rate of hydroboration; conversion;98%
(+)-α-pinene
7785-70-8

(+)-α-pinene

pinanediol
18680-27-8

pinanediol

Conditions
ConditionsYield
With osmium(VIII) oxide; trimethylamine-N-oxide In pyridine; water; tert-butyl alcohol for 96h; Heating;96.5%
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; water In tert-butyl alcohol for 24h; Reflux;96.5%
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In tert-butyl alcohol for 24h; Inert atmosphere; Reflux;91%
(+)-α-pinene
7785-70-8

(+)-α-pinene

(1S,3S)-3-acetyl-2,2-dimethylcyclobutaneacetaldehyde1,6-cyclodecanedione
71628-89-2

(1S,3S)-3-acetyl-2,2-dimethylcyclobutaneacetaldehyde1,6-cyclodecanedione

Conditions
ConditionsYield
Stage #1: (+)-α-pinene With ozone In dichloromethane; isopropyl alcohol at -78℃;
Stage #2: With ring-opening metathesis polymer-supported triphenylphosphine In dichloromethane; isopropyl alcohol at 20℃; for 2h; Further stages.;
96%
Stage #1: (+)-α-pinene With oxygen; ozone In dichloromethane at -78℃; Schlenk technique;
Stage #2: With triphenylphosphine In dichloromethane at -78 - 20℃;
36%
With ozone
(+)-α-pinene
7785-70-8

(+)-α-pinene

(1S,2S,4R,6S)-2,7,7-trimethyl-3-oxatricyclo [4.1.1.02,4]octane

(1S,2S,4R,6S)-2,7,7-trimethyl-3-oxatricyclo [4.1.1.02,4]octane

Conditions
ConditionsYield
With oxygen; isobutyraldehyde In acetonitrile at 25℃; for 2h; Reagent/catalyst;96%
With 1,3,5-trichlorobenzene; iodosylbenzene; C38H35ClN4OPRu(1+)*Cl(1-); trifluoroacetic acid In 1,1,2,2-tetrachloroethane at 30℃; for 19h;32%
(+)-α-pinene
7785-70-8

(+)-α-pinene

C16H21NO3S2

C16H21NO3S2

Conditions
ConditionsYield
In diethyl ether at 0℃; for 16h;95%
(+)-α-pinene
7785-70-8

(+)-α-pinene

C10H16(2)H2

C10H16(2)H2

Conditions
ConditionsYield
With deuterium; Wilkinson's catalyst In toluene93.5%
(+)-α-pinene
7785-70-8

(+)-α-pinene

methyl 2-(4-bromophenyl)-2-diazoacetate

methyl 2-(4-bromophenyl)-2-diazoacetate

methyl (αR,1R,4R,6S)-α-(3,5,5-trimethylbicyclo[3.1.1]hept-2-en-1-yl)-(4-bromophenyl)acetate
380500-01-6

methyl (αR,1R,4R,6S)-α-(3,5,5-trimethylbicyclo[3.1.1]hept-2-en-1-yl)-(4-bromophenyl)acetate

Conditions
ConditionsYield
With dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) In various solvent(s) at 23℃; for 3h;93%
C30H45BO

C30H45BO

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-1-Phenyl-3-buten-1-ol
77118-87-7

(S)-1-Phenyl-3-buten-1-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; isobutyraldehyde at 65℃; for 12h;A 90%
B 90%
diisopinocampheylborane
21932-54-7

diisopinocampheylborane

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
Stage #1: With benzaldehyde at 50℃; Oxidation;
Stage #2: diisopinocampheylborane With boron trifluoride diethyl etherate at 100℃; for 1h; Oxidation;
86%
C28H47BO

C28H47BO

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1R,1'R)-(+)-1-(2-cyclohexenyl)-1-ethanol
95674-80-9

(1R,1'R)-(+)-1-(2-cyclohexenyl)-1-ethanol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; isobutyraldehyde at 65℃; for 12h;A 84%
B 67%
diisopinocampheylborane

diisopinocampheylborane

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
Stage #1: diisopinocampheylborane With benzaldehyde Inert atmosphere; Cooling with ice;
Stage #2: With boron trifluoride diethyl etherate at 100℃; for 1h; Inert atmosphere;
71%
(1S,4R,5R)-3-iodo-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene
911673-20-6

(1S,4R,5R)-3-iodo-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
473-62-1

(1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

C

6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene
190715-28-7

6,6-dimethyl4-methylidenebicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
Stage #1: (1S,4R,5R)-3-iodo-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene With potassium tert-butylate In diethylene glycol dimethyl ether at 170℃; for 8h;
Stage #2: With silica gel In hexane
A 6%
B 32%
C 54%
(-)-isopinocamphyl tosylate
62697-75-0

(-)-isopinocamphyl tosylate

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene
24031-98-9

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110℃; for 3h; Title compound not separated from byproducts.;A 45%
B 45%
(-)-isopinocampheol
1196-00-5

(-)-isopinocampheol

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(+)-pinocamphyl chloride
185378-26-1

(+)-pinocamphyl chloride

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine for 16h; Heating;A n/a
B 30%

A

(-)-α-pinene
7785-26-4

(-)-α-pinene

B

(+)-α-pinene
7785-70-8

(+)-α-pinene

C

2,4,4-Trimethyl-8-methylene-3-aza-bicyclo[3.3.1]non-2-ene

2,4,4-Trimethyl-8-methylene-3-aza-bicyclo[3.3.1]non-2-ene

Conditions
ConditionsYield
With chloranil In dichloromethane; acetonitrile Irradiation; Yield given;A n/a
B n/a
C 5%
ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(-)-trans-δ-pinene
24031-99-0

(-)-trans-δ-pinene

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene
24031-98-9

(1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene

rac-α-pinene
80-56-8

rac-α-pinene

A

(-)-α-pinene
7785-26-4

(-)-α-pinene

B

(+)-α-pinene
7785-70-8

(+)-α-pinene

Conditions
ConditionsYield
Leiten des Dampfes durch Gelatine-Hydrosol;
(+)-pinocamphone-hydrazone

(+)-pinocamphone-hydrazone

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(-)-trans-δ-pinene
24031-99-0

(-)-trans-δ-pinene

Conditions
ConditionsYield
With ethanol; mercury(II) oxide
Conditions
ConditionsYield
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) toluene, -50 deg C, 1h, 2.) toluene, 26 deg C, 10h; Yield given. Multistep reaction. Yields of byproduct given;
cyclopinene
73956-74-8

cyclopinene

A

Beta-pinene
177698-19-0

Beta-pinene

B

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

C

camphene
79-92-5

camphene

D

2-menthene
5256-65-5

2-menthene

E

(+)-α-pinene
7785-70-8

(+)-α-pinene

F

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With KU 21 cation-exchange resin In hexane at 70℃; for 1h; Product distribution;A 4 % Chromat.
B n/a
C 3 % Chromat.
D n/a
E 76 % Chromat.
F n/a

A

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

B

(+)-α-pinene
7785-70-8

(+)-α-pinene

C

cyclopinene
73956-74-8

cyclopinene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 5h; Heating; Yield given. Yields of byproduct given;
benzaldehyde
100-52-7

benzaldehyde

(4aR,8aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-benzo[b]borinine
175656-35-6

(4aR,8aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-benzo[b]borinine

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,8aR)-1-Benzyloxy-decahydro-benzo[b]borinine
878381-35-2

(4aR,8aR)-1-Benzyloxy-decahydro-benzo[b]borinine

Conditions
ConditionsYield
In diethyl ether at 0℃; for 6h; Elimination;
benzaldehyde
100-52-7

benzaldehyde

(4aR,9aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-1-bora-benzocycloheptene

(4aR,9aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-decahydro-1-bora-benzocycloheptene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,9aR)-1-Benzyloxy-decahydro-1-bora-benzocycloheptene

(4aR,9aR)-1-Benzyloxy-decahydro-1-bora-benzocycloheptene

Conditions
ConditionsYield
In diethyl ether at 0℃; Elimination;
benzaldehyde
100-52-7

benzaldehyde

(4aR,10aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-dodecahydro-1-bora-benzocyclooctene

(4aR,10aR)-1-((1R,2S,3R,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-3-yl)-dodecahydro-1-bora-benzocyclooctene

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(4aR,10aR)-1-Benzyloxy-dodecahydro-1-bora-benzocyclooctene

(4aR,10aR)-1-Benzyloxy-dodecahydro-1-bora-benzocyclooctene

Conditions
ConditionsYield
In diethyl ether at 0℃; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(R)-2-Ethyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(R)-2-Ethyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(R)-1-Ethoxy-2-ethyl-borolane

(R)-1-Ethoxy-2-ethyl-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
acetaldehyde
75-07-0

acetaldehyde

(S)-2-Isopropyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

(S)-2-Isopropyl-1-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borolane

A

(+)-α-pinene
7785-70-8

(+)-α-pinene

B

(S)-1-Ethoxy-2-isopropyl-borolane

(S)-1-Ethoxy-2-isopropyl-borolane

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Elimination;
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