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79-92-5

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79-92-5 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 79-92-5 differently. You can refer to the following data:
1. WHITE CRYSTALLINE LOW MELTING SOLID
2. Camphene has a terpene, camphoraceous taste.

Occurrence

Reported found in carrot, dill, fennel, marjoram, nutmeg, parsley, pepper, tarragon and thyme.

Uses

Different sources of media describe the Uses of 79-92-5 differently. You can refer to the following data:
1. Camphene is used in the preparation of fragrances and as a food additive for flavoring.
2. Manufacture of synthetic camphor, camphor substitute.

Definition

ChEBI: A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.

Preparation

From pinene by catalytic isomerization or from bornyl chloride by heating with alkali in the presence of abietenesulfonic acid.

Aroma threshold values

Detection at 10%: camphoraceous, cooling, piney woody with terphy nuances. It has citrus and green minty and green spicy notes.

Taste threshold values

Taste characteristics at 50–100 ppm: camphoraceous, cooling, minty, with citrus and green spicy nuances.

General Description

A colorless to white crystalline solid with an insipid camphor-like odor. Dust and crystals are irritants to the eyes, nose and throat. Emits flammable vapors when heated. Emits acrid smoke and irritating fumes at high temperature. Used for the manufacture of synthetic camphor.

Reactivity Profile

Camphene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.

Hazard

Toxic by ingestion.

Flammability and Explosibility

Flammable

Pharmacology

Oral administration of camphene (260 mmols/kg) to rats increased bile flow by 50% 4 hr after administration (M?rsdorf, 1966). Development of atheromatosis of the aorta in rabbits fed 1 g cholesterol/day for 3 months was considerably inhibited by simultaneous administration of a mixture of terpenes including camphene, injected sc in a dose of 1 ml every other day for 6 wk and then given orally in doses of 2 ml/day (Benk?, Macher, Szarvas & Tiboldi, 1961). The effect of 1 g cholesterol/day for 8 wk in the diet of rabbits in increasing the number and volume of mast cells in the aortic adventitia and increasing the total lipid content of the aortic wall was slightly enhanced by the simultaneous addition of 11 g camphene/day (Lesznyak, Benko, Szabo & Muller, 1972). This camphene treatment also decreased the lipid accumulation in the liver, but had no effect on the cholesterol-induced atheromatosis of the aorta (Benko, Szabo, Muller & Lesznyak, 1972).

Anticancer Research

This was tested against melanoma cells in a syngeneic model, and there was promisingantitumor activity (Ma et al. 2016).

Safety Profile

Mutation data reported. Combustible; yields flammable vapors when heated and can react with oxidizing materials. To fight fire, use water spray, foam, fog, CO2. When heated to decomposition it emits acrid smoke and irritating fumes.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 79-92-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 79-92:
(4*7)+(3*9)+(2*9)+(1*2)=75
75 % 10 = 5
So 79-92-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3

79-92-5 Well-known Company Product Price

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

  • (C0009)  (±)-Camphene (contains ca. 20% Tricyclene)  >78.0%(GC)

  • 79-92-5

  • 25g

  • 130.00CNY

  • Detail
  • TCI America

  • (C0009)  (±)-Camphene (contains ca. 20% Tricyclene)  >78.0%(GC)

  • 79-92-5

  • 500g

  • 460.00CNY

  • Detail
  • Alfa Aesar

  • (A18040)  (±)-Camphene, tech. (sum of camphene + fenchene)   

  • 79-92-5

  • 50g

  • 519.0CNY

  • Detail
  • Alfa Aesar

  • (A18040)  (±)-Camphene, tech. (sum of camphene + fenchene)   

  • 79-92-5

  • 250g

  • 772.0CNY

  • Detail
  • Alfa Aesar

  • (A18040)  (±)-Camphene, tech. (sum of camphene + fenchene)   

  • 79-92-5

  • 1000g

  • 2207.0CNY

  • Detail
  • Supelco

  • (442505)  Camphene  analytical standard

  • 79-92-5

  • 000000000000442505

  • 234.00CNY

  • Detail
  • Sigma-Aldrich

  • (01410590)  Camphene  primary pharmaceutical reference standard

  • 79-92-5

  • 01410590-100MG

  • 3,039.66CNY

  • Detail

79-92-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name camphene

1.2 Other means of identification

Product number -
Other names 2-tert-butyl-acrylaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
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:79-92-5 SDS

79-92-5Synthetic route

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

camphene
79-92-5

camphene

Conditions
ConditionsYield
molybdophosphoric acid; silica gel In chloroform for 0.5h; Heating;99%
With bis(2,2,2-trifluoroethoxy)triphenylphosphorane61%
With sulfuric acid; water dl-camphene;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

C10H14S2
142039-34-7

C10H14S2

camphene
79-92-5

camphene

Conditions
ConditionsYield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; diethyl ether for 10h; Heating;82%
endo-borneol
464-45-9

endo-borneol

A

camphene
79-92-5

camphene

B

bornan-exo-2-yl bromide
4443-48-5

bornan-exo-2-yl bromide

Conditions
ConditionsYield
With carbon tetrabromide; polystyrene-supported triphenylphosphine In chloroform at 20℃; for 16h;A 2%
B 82%
ω,ω-dibromocamphene
70389-76-3

ω,ω-dibromocamphene

A

camphene
79-92-5

camphene

B

3,3-dimethyl-2-(bromomethylene)bicyclo<2.2.1>heptane
70234-75-2

3,3-dimethyl-2-(bromomethylene)bicyclo<2.2.1>heptane

Conditions
ConditionsYield
With methanol for 16h; Product distribution; Mechanism; Ambient temperature; Irradiation;A n/a
B 82%
With methanol for 16h; Ambient temperature; Irradiation;A n/a
B 82%
With methanol for 16h; Ambient temperature; Irradiation;
exo-2-nitroaminobornane
91087-37-5, 124666-29-1

exo-2-nitroaminobornane

A

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane
508-32-7

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane

B

camphene
79-92-5

camphene

Conditions
ConditionsYield
at 130℃; for 60h;A 9%
B 81%
(+/-)-1,3,4-trichloro-2-isobornyloxy-5,5-dimethoxycyclopentadiene

(+/-)-1,3,4-trichloro-2-isobornyloxy-5,5-dimethoxycyclopentadiene

A

camphene
79-92-5

camphene

B

(+/-)-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one
81849-86-7

(+/-)-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one

Conditions
ConditionsYield
at 20℃; for 720h; Decomposition;A 75%
B 80%
2-chlorobornane
559-45-5

2-chlorobornane

acetonitrile
75-05-8

acetonitrile

A

camphene
79-92-5

camphene

N-(2-exo-1,7,7-trimethylbicyclo<2.2.1>heptyl)acetamide
6627-20-9, 7362-52-9, 24629-80-9, 91690-03-8, 94319-77-4, 94347-61-2, 107494-22-4

N-(2-exo-1,7,7-trimethylbicyclo<2.2.1>heptyl)acetamide

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 1h;A 6%
B 66%
Beta-pinene
177698-19-0

Beta-pinene

B

1-methyl-4-isopropenylbenzene
1195-32-0

1-methyl-4-isopropenylbenzene

C

camphene
79-92-5

camphene

D

C20H32

C20H32

E

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With hydrogen at 140℃; for 4h; Temperature; Reagent/catalyst;A n/a
B n/a
C n/a
D 65.6%
E n/a

A

ethene
74-85-1

ethene

B

1,7,7-trimethylbicyclo[2.2.1]hept-2-ene
464-17-5

1,7,7-trimethylbicyclo[2.2.1]hept-2-ene

C

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane
508-32-7

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane

D

camphene
79-92-5

camphene

E

1,5,5-trimethyl-cyclopenta-1,3-diene
4249-09-6

1,5,5-trimethyl-cyclopenta-1,3-diene

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
at 320℃; Kinetics; pyrolysis, other temperature;A n/a
B 22.3%
C 14.8%
D 50.1%
E n/a
F n/a
(E)-ω-bromocamphene
51361-78-5

(E)-ω-bromocamphene

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

A

camphene
79-92-5

camphene

B

ω-sulphoxymethylcamphene
81373-62-8, 81373-63-9

ω-sulphoxymethylcamphene

Conditions
ConditionsYield
With potassium tert-butylate at 100℃; for 6h; Product distribution;A 48%
B 32%
With potassium tert-butylate at 100℃; for 6h;A 48%
B 32%
acetic acid
64-19-7

acetic acid

A

Terpinolene
586-62-9

Terpinolene

B

camphene
79-92-5

camphene

C

terpinyl acetate
80-26-2

terpinyl acetate

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With 1-(3-sulfonic acid)propyl-3-poly(ethylene glycol) octadecylamine polyoxyethylene ether tetrafluoroborate at 30℃; for 10h; Catalytic behavior; Concentration; Reagent/catalyst; Temperature; Time;A 13.99 %Chromat.
B 17.23 %Chromat.
C 35.7%
D 16.55 %Chromat.
isobornyl chloride
464-41-5

isobornyl chloride

aniline
62-53-3

aniline

A

camphene
79-92-5

camphene

Conditions
ConditionsYield
at 185℃; for 5h;A n/a
B 31.3%

A

Terpinolene
586-62-9

Terpinolene

B

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

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

C

camphene
79-92-5

camphene

D

crithmene
99-85-4

crithmene

E

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With Conventional beta-zeolite at 70℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Reflux;A 8.7%
B 7.2%
C 19.7%
D 4.4%
E 30.7%
With mesoporous beta type zeolite at 70℃; for 0.5h;

A

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

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

B

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane
508-32-7

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane

C

camphene
79-92-5

camphene

D

crithmene
99-85-4

crithmene

Conditions
ConditionsYield
thionin-supported zeolite Na-Y In hexane at 20℃; for 0.5h; Product distribution;A 20%
B 2%
C 20%
D 18%
Conditions
ConditionsYield
With mineral acids dl-camphene;
d-borneol
464-43-7

d-borneol

camphene
79-92-5

camphene

Conditions
ConditionsYield
With Japanese acid earth at 210 - 220℃; bei der Destillation; d-camphene;
With copper(I) sulfate; copper; copper(II) sulfate at 330℃; d-camphene;
bornan-exo-2-yl bromide
4443-48-5

bornan-exo-2-yl bromide

camphene
79-92-5

camphene

Conditions
ConditionsYield
With sodium acetate; acetic acid dl-camphene;
Multi-step reaction with 2 steps
1: lime milk / 135 - 150 °C
View Scheme
bornylamine
4481-88-3

bornylamine

camphene
79-92-5

camphene

Conditions
ConditionsYield
With acetic anhydride at 200 - 210℃; dl-camphene;
(Ξ)-phosphonic acid ethyl ester-((1S)-bornyl ester)
108248-52-8

(Ξ)-phosphonic acid ethyl ester-((1S)-bornyl ester)

camphene
79-92-5

camphene

Conditions
ConditionsYield
at 320℃;
rac-endo-borneol
6627-72-1

rac-endo-borneol

camphene
79-92-5

camphene

Conditions
ConditionsYield
With fired clay; copper(II) oxide at 200 - 220℃; in einer Wasserstoffatmosphaere unter hohem Druck;
With sulfuric acid
zum Mechanismus der Bildung;
bornyl iodide
90977-38-1

bornyl iodide

camphene
79-92-5

camphene

rac-α-pinene
80-56-8

rac-α-pinene

camphene
79-92-5

camphene

Conditions
ConditionsYield
With bromine dl-camphene;
With sulfuric acid dl-camphene;
dl-camphene;
With acetic acid at 200℃; in geschlossenem Gefaess; dl-camphene;
Multi-step reaction with 2 steps
1: hydrogen bromide
2: sodium acetate; glacial acetic acid
View Scheme
(1R,2S)-N-(1,7,7-trimethyl-2-norbornyl)formamide
24629-79-6, 71697-80-8, 71697-81-9, 86391-06-2, 74183-27-0

(1R,2S)-N-(1,7,7-trimethyl-2-norbornyl)formamide

camphene
79-92-5

camphene

Conditions
ConditionsYield
With acetic anhydride at 200 - 210℃; dl-camphene;
bornyl-picryl ether

bornyl-picryl ether

camphene
79-92-5

camphene

Conditions
ConditionsYield
at 175℃; d-camphene;
tricyclene
508-32-7

tricyclene

camphene
79-92-5

camphene

Conditions
ConditionsYield
at 180 - 200℃; beim Leiten ueber Nickel im Stickstoffstrom;
With sodium hydrogen sulfate at 168℃;
With sodium pyrosulfate at 168℃; dl-camphene;
methanol
67-56-1

methanol

B

camphene
79-92-5

camphene

C

4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene
14576-08-0

4-(2-methoxypropan-2-yl)-1-methylcyclohex-1-ene

F

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With sodium methylate at 35℃;A 25 % Chromat.
B 3 % Chromat.
C 18 % Chromat.
D 5 % Chromat.
E 28 % Chromat.
F 8 % Chromat.
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2,2,2-Trichloro-acetimidic acid 2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester
148952-14-1

2,2,2-Trichloro-acetimidic acid 2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester

B

camphene
79-92-5

camphene

C

2-tert-Butylperoxy-2,6,6-trimethyl-bicyclo[3.1.1]heptane

2-tert-Butylperoxy-2,6,6-trimethyl-bicyclo[3.1.1]heptane

D

4-(1-tert-Butylperoxy-1-methyl-ethyl)-1-methyl-cyclohexene

4-(1-tert-Butylperoxy-1-methyl-ethyl)-1-methyl-cyclohexene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In pentane 1.) -5 deg C, 15 min, 2.) up to r.t.; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2,2,2-Trichloro-acetimidic acid 2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester
148952-14-1

2,2,2-Trichloro-acetimidic acid 2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester

A

camphene
79-92-5

camphene

B

2-tert-Butylperoxy-2,6,6-trimethyl-bicyclo[3.1.1]heptane

2-tert-Butylperoxy-2,6,6-trimethyl-bicyclo[3.1.1]heptane

C

4-(1-tert-Butylperoxy-1-methyl-ethyl)-1-methyl-cyclohexene

4-(1-tert-Butylperoxy-1-methyl-ethyl)-1-methyl-cyclohexene

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In pentane 1.) -5 deg C, 15 min, 2.) up to r.t.; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
Beta-pinene
177698-19-0

Beta-pinene

B

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

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

C

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane
508-32-7

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane

D

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

E

camphene
79-92-5

camphene

F

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
Pt/Al at 300℃; for 1.2h; Product distribution; Mechanism; catalytic transformation investigated on different catalyst with different contact time and temperature; further products determined;
carbon monoxide
201230-82-2

carbon monoxide

camphene
79-92-5

camphene

(3,3-dimethyl-[2]norbornyl)-acetaldehyde
39850-66-3

(3,3-dimethyl-[2]norbornyl)-acetaldehyde

Conditions
ConditionsYield
With hydrogen In toluene at 80℃; under 30402 Torr; for 24h; Catalytic behavior; Autoclave;100%
camphene
79-92-5

camphene

3,3-dimethyl-spiro[norbornan-2,2'-oxirane]
875-03-6, 62318-94-9, 69685-54-7, 69685-55-8, 90365-31-4

3,3-dimethyl-spiro[norbornan-2,2'-oxirane]

Conditions
ConditionsYield
With NH-pyrazole; peracetic acid; methyltrioxorhenium(VII) In dichloromethane; water at 20℃; for 3h; Catalytic behavior; Concentration; Reagent/catalyst; Solvent; Temperature; Time;97%
With N-hydroxyphthalimide; oxygen; acetaldehyde In acetonitrile at 60℃; under 760.051 Torr; for 4h; Minisci epoxidation; Continuous flow reactor;73%
With oxygen; isobutyraldehyde; cobalt dichloride In acetonitrile at 25℃;72%
Conditions
ConditionsYield
With oxygen; zirconium(IV) chloride; diisobutylaluminium hydride In tolueneA 4%
B 96%
With oxygen; zirconium(IV) chloride; diisobutylaluminium hydride 1.) toluene, 7 h, 70 deg C; Multistep reaction;
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

camphene
79-92-5

camphene

aluminium bromide
7727-15-3

aluminium bromide

C10H17AlBr2

C10H17AlBr2

Conditions
ConditionsYield
In diethyl ether; benzene Ar, LiAlH4 in ether added to benzene under stirring, most of the solvent removed, benzene and AlBr3 in benzene added, stirred at 20°C for 1 h, org. compound in benzene added drowise under stirring, warmed to 30-40°C for 5-10 min; NMR;96%
carbon monoxide
201230-82-2

carbon monoxide

camphene
79-92-5

camphene

N-butylamine
109-73-9

N-butylamine

C15H29N
1350552-86-1

C15H29N

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 20h; Inert atmosphere;94%
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 20h; Inert atmosphere;
camphene
79-92-5

camphene

A

(+-)-camphenilone
13211-15-9

(+-)-camphenilone

B

4,4-dimethyl-3-oxabicyclo<3.2.1>octan-2-one
66471-65-6

4,4-dimethyl-3-oxabicyclo<3.2.1>octan-2-one

Conditions
ConditionsYield
With ozone In chloroform for 3.5h;A 5%
B 93%
methanol
67-56-1

methanol

camphene
79-92-5

camphene

exo-2-Methoxy-1,7,7-trimethylbicyclo[2.2.1]heptane
4443-51-0, 5331-32-8, 10395-54-7, 30199-22-5, 30199-23-6, 113626-77-0

exo-2-Methoxy-1,7,7-trimethylbicyclo[2.2.1]heptane

Conditions
ConditionsYield
phosphotungstic acid at 65℃; for 5h;92.5%
With dodecatungstosilic acid at 65℃; for 3h; Product distribution; Further Variations:; Reagents; Addition; rearrangement;
ethanol
64-17-5

ethanol

camphene
79-92-5

camphene

ethyl isobornyl ether

ethyl isobornyl ether

Conditions
ConditionsYield
phosphotungstic acid at 65℃; for 5h;92.5%
With dodecatungstosilic acid at 65℃; for 3h; Product distribution; Further Variations:; Reagents; Addition; rearrangement;
camphene
79-92-5

camphene

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butyl isobornyl ether

tert-butyl isobornyl ether

Conditions
ConditionsYield
dodecatungstosilic acid at 65℃; for 5h;92.5%
With dodecatungstosilic acid at 65℃; for 3h; Product distribution; Further Variations:; Reagents; Addition; rearrangement;
camphene
79-92-5

camphene

phenylmethanethiol
100-53-8

phenylmethanethiol

benzyl (1,7,7-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

benzyl (1,7,7-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

benzyl (2,3,3-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

benzyl (2,3,3-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

Conditions
ConditionsYield
In(OSO2CF3)3 In 1,2-dichloro-ethane Heating;A 92%
B 72%
camphene
79-92-5

camphene

ethanethiol
75-08-1

ethanethiol

ethyl (2,3,3-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

ethyl (2,3,3-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

ethyl (1,7,7-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

ethyl (1,7,7-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

Conditions
ConditionsYield
In(OSO2CF3)3 In 1,2-dichloro-ethane at -8℃; for 7h;A 65%
B 91%
camphene
79-92-5

camphene

O,O-Diethyl hydrogen phosphorodithioate
298-06-6

O,O-Diethyl hydrogen phosphorodithioate

Dithiophosphoric acid O,O'-diethyl ester S-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl) ester

Dithiophosphoric acid O,O'-diethyl ester S-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl) ester

Conditions
ConditionsYield
1.) r.t., 30 min, 2.) 80-100 deg C, 12 h;90%
camphene
79-92-5

camphene

acetonitrile
75-05-8

acetonitrile

N-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)acetamide
91690-03-8

N-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)acetamide

Conditions
ConditionsYield
With iron(III) perchlorate Ambient temperature;90%
With phosphotungstic acid; 1,7,7-trimethyltricyclo[2.2.1.02,6]heptane In water at 80℃; for 8h; Ritter reaction;67%
quinoline
91-22-5

quinoline

camphene
79-92-5

camphene

2-((3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)quinoline

2-((3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)quinoline

Conditions
ConditionsYield
With tricyclohexylphosphonium chloride; [(1,5-cyclooctadiene)2RhCl]2 In tetrahydrofuran at 165℃; for 19h;90%
camphene
79-92-5

camphene

4-(pentafluoro-λ6-sulfaneyl)benzenediazonium tetrafluoroborate
1605274-62-1

4-(pentafluoro-λ6-sulfaneyl)benzenediazonium tetrafluoroborate

C16H19F5S

C16H19F5S

Conditions
ConditionsYield
With palladium diacetate In ethanol; water at 20℃; for 16h; Heck Reaction;89%
With palladium diacetate In ethanol; water at 20℃; for 16h; Heck Reaction;89%
camphene
79-92-5

camphene

thioacetic acid
507-09-5

thioacetic acid

(3,3-dimethylbicyclo[2.2.1]hept-2-yl)methyl exo-thioacetate

(3,3-dimethylbicyclo[2.2.1]hept-2-yl)methyl exo-thioacetate

2,3,3-trimethylbicyclo[2.2.1]hept-2-yl exo-thioacetate

2,3,3-trimethylbicyclo[2.2.1]hept-2-yl exo-thioacetate

1,7,7-trimethylbicyclo[2.2.1]hept-2-yl exo-thioacetate

1,7,7-trimethylbicyclo[2.2.1]hept-2-yl exo-thioacetate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 12h;A 88%
B 73%
C 77%
morpholine
110-91-8

morpholine

carbon monoxide
201230-82-2

carbon monoxide

camphene
79-92-5

camphene

C15H27NO
88100-38-3

C15H27NO

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 22h; Inert atmosphere;87%
Octanethiol
111-88-6

Octanethiol

camphene
79-92-5

camphene

octyl (2,3,3-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

octyl (2,3,3-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

octyl (1,7,7-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

octyl (1,7,7-trimethylbicyclo[2.2.1]hept-2-yl) exo-sulfide

Conditions
ConditionsYield
In(OSO2CF3)3 In 1,2-dichloro-ethane at 84℃;A 69%
B 85%
Dichloromethylsilane
75-54-7

Dichloromethylsilane

camphene
79-92-5

camphene

Dichloro-(3,3-dimethyl-bicyclo[2.2.1]hept-2-ylmethyl)-methyl-silane

Dichloro-(3,3-dimethyl-bicyclo[2.2.1]hept-2-ylmethyl)-methyl-silane

Conditions
ConditionsYield
With dihydrogen hexachloroplatinate In isopropyl alcohol83.6%
carbon monoxide
201230-82-2

carbon monoxide

camphene
79-92-5

camphene

dibutylamine
111-92-2

dibutylamine

optically inactive dibutyl-[2-(3,3-dimethyl-[2]norbornyl)-ethyl]-amine
102180-80-3

optically inactive dibutyl-[2-(3,3-dimethyl-[2]norbornyl)-ethyl]-amine

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 22h; Inert atmosphere;83%
With methoxy(cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In toluene at 100℃; under 45603.1 Torr; for 4h; Inert atmosphere;
camphene
79-92-5

camphene

2,2,3-trimethyl-bicyclo[2.2.1]heptane
473-19-8

2,2,3-trimethyl-bicyclo[2.2.1]heptane

Conditions
ConditionsYield
With hydrogen; lithium aluminium tetrahydride; nickelocene In tetrahydrofuran Ambient temperature; atmospheric pressure;82%
With oxygen; hydrazine hydrate In propan-1-ol at 100℃; under 15001.5 Torr; for 0.166667h; Flow reactor;
thiobenzoic acid
98-91-9

thiobenzoic acid

camphene
79-92-5

camphene

(3,3-dimethylbicyclo[2.2.1]hept-2-yl)methyl exo-thiobenzoate

(3,3-dimethylbicyclo[2.2.1]hept-2-yl)methyl exo-thiobenzoate

2,3,3-trimethylbicyclo[2.2.1]hept-2-yl exo-thiobenzoate

2,3,3-trimethylbicyclo[2.2.1]hept-2-yl exo-thiobenzoate

1,7,7-trimethylbicyclo[2.2.1]hept-2-yl exo-thiobenzoate

1,7,7-trimethylbicyclo[2.2.1]hept-2-yl exo-thiobenzoate

Conditions
ConditionsYield
In(OSO2CF3)3 In 1,2-dichloro-ethane at 84℃;A 11%
B 59%
C 81%
camphene
79-92-5

camphene

recorcinol
108-46-3

recorcinol

4-(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-benzene-1,3-diol

4-(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-benzene-1,3-diol

4,6-bis(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzene-1,3-diol

4,6-bis(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzene-1,3-diol

C

4,6-bis(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzene-1,3-diol

4,6-bis(exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzene-1,3-diol

Conditions
ConditionsYield
With isopropyl alcohol; aluminium at 120℃; for 7h; Reagent/catalyst; Temperature; Time;A 81%
B n/a
C n/a
camphene
79-92-5

camphene

trichloro-(3,3-dimethyl-[2]norbornylmethyl)-silane
4563-52-4

trichloro-(3,3-dimethyl-[2]norbornylmethyl)-silane

Conditions
ConditionsYield
With dihydrogen hexachloroplatinate; trichlorosilane In isopropyl alcohol80.2%
With trichlorosilane at 280℃;

79-92-5Relevant articles and documents

Lockhart

, p. 219,224 (1974)

Highly-selective solvent-free catalytic isomerization of α-pinene to camphene over reusable titanate nanotubes

Huang, Geng,Liu, Jian,Su, Shengpei,Yin, Dulin,Zhou, Shuolin

, p. 10606 - 10611 (2020)

Titanate nanotubes, prepared by the hydrothermal reconstitution and modification with hydrochloric acid, were tested as solid acid catalysts in the isomerization of α-pinene under solvent free conditions. The results showed that titanate nanotubes have be

-

Wolinsky,J.,Eustace,E.J.

, p. 3654 - 3658 (1975)

-

Discovering Monoterpene Catalysis Inside Nanocapsules with Multiscale Modeling and Experiments

Pahima, Efrat,Zhang, Qi,Tiefenbacher, Konrad,Major, Dan T.

, p. 6234 - 6246 (2019/04/25)

Large-scale production of natural products, such as terpenes, presents a significant scientific and technological challenge. One promising approach to tackle this problem is chemical synthesis inside nanocapsules, although enzyme-like control of such chemistry has not yet been achieved. In order to better understand the complex chemistry inside nanocapsules, we design a multiscale nanoreactor simulation approach. The nanoreactor simulation protocol consists of hybrid quantum mechanics-molecular mechanics-based high temperature Langevin molecular dynamics simulations. Using this approach we model the tail-to-head formation of monoterpenes inside a resorcin[4]arene-based capsule (capsule I). We provide a rationale for the experimentally observed kinetics of monoterpene product formation and product distribution using capsule I, and we explain why additional stable monoterpenes, like camphene, are not observed. On the basis of the in-capsule I simulations, and mechanistic insights, we propose that feeding the capsule with pinene can yield camphene, and this proposal is verified experimentally. This suggests that the capsule may direct the dynamic reaction cascades by virtue of π-cation interactions.

Wijayati,Handayani,Supartono

, p. 1705 - 1708 (2017/06/27)

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