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564-94-3

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564-94-3 Usage

Description

2-Formyl-6,6-dimethylbicyclo(3.1.1 -)hept-2-ene has a refreshing, spicy-herbaceous odor of bay leaf, reminiscent of cinnamon. This substance may be synthesized from myrtenol by oxidation with chromic acid; by isolation from higher-than-cineole boiling fractions in the distillation of eucalyptus oil.

Chemical Properties

Different sources of media describe the Chemical Properties of 564-94-3 differently. You can refer to the following data:
1. 2-Formyl-6,6-dimethylbicyclo(3 1 1)hept-2-ene has a refreshing, spicy, herbaceous odor of bay leaf, reminiscent of cinnamon.
2. CLEAR COLOURLESS TO YELLOW LIQUID

Occurrence

Reported found in the oils from leaves of Eucalyptus globulus and Callytrix tetragona; in the oils of Hernandia pel- tata and Perovskia abrotanoides; in the oils from wood of Chamaecyparis formonensis and Chamaecyparis obtuse; also in cumin seeds and in mint Reported found in orange peel oil, ginger, juniper berry, pepper, peppermint, Scotch spearmint, peppermint oil, parsley seed oil, licorice, laurel, myrtle leaf, calabash nutmeg (Monadora myristica Dunal), Roman chamomile, eucalyptus oil and mastic gum oil

Preparation

From myrtenol by oxidation with chromic acid; by isolation from higher-than-cineole boiling fractions in the distillation of eucalyptus oil.

Taste threshold values

Taste characteristics at 30 ppm: woody, piney, minty, green cooling, slightly powdery and spicy.

Check Digit Verification of cas no

The CAS Registry Mumber 564-94-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 4 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 564-94:
(5*5)+(4*6)+(3*4)+(2*9)+(1*4)=83
83 % 10 = 3
So 564-94-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3/t8-,9-/m0/s1

564-94-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Myrtenal

1.2 Other means of identification

Product number -
Other names Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:564-94-3 SDS

564-94-3Synthetic route

myrtenol
515-00-4

myrtenol

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With bromobenzene; sodium hydride; triphenylphosphine; palladium diacetate In tetrahydrofuran at 65℃; for 1h;100%
With bromobenzene; sodium hydride; palladium diacetate; triphenylphosphine In tetrahydrofuran at 65℃; for 1h;95%
With calcium hydride; oxygen; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper dichloride In acetonitrile at 25℃; for 3h;93%
2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-[1,3]dioxolane

2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-[1,3]dioxolane

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With carbon tetrabromide In water; acetonitrile at 45℃; for 2h; sonication;99%
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With pentafluorobenzeneseleninic acid In benzene for 2h; Heating;85%
With selenium(IV) oxide In 1,4-dioxane; ethanol at 60℃;70%
With perfluorooctylselenic acid; iodosylbenzene In various solvent(s) Heating;62%
With selenium(IV) oxide
With selenium(IV) oxide In 1,4-dioxane; ethanol at 65 - 95℃;

A

myrtenol
515-00-4

myrtenol

B

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With 2-(N-oxido)pyridineseleninic anhydride In dichloromethane at 20℃; for 18h;A 57%
B 28%
myrtenol
515-00-4

myrtenol

phenol
108-95-2

phenol

A

7,7-dimethyl-2-(hydroxymethyl)bicyclo<3.1.1>heptane
514-99-8

7,7-dimethyl-2-(hydroxymethyl)bicyclo<3.1.1>heptane

B

4-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)phenol

4-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)phenol

C

3-(2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methoxy)benzyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

3-(2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methoxy)benzyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

D

4-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-9-isopropyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene
1344744-38-2

4-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-9-isopropyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene

E

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: myrtenol; phenol With aluminum isopropoxide at 160℃;
Stage #2: With hydrogenchloride In water
A n/a
B 1.5%
C 12%
D n/a
E 6%
dichloromethane
75-09-2

dichloromethane

peroxyde de t-butyle et de myrtenyle
81971-91-7

peroxyde de t-butyle et de myrtenyle

3-dichloromethyl-2,10-epoxypinane

3-dichloromethyl-2,10-epoxypinane

B

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With sodium carbonate at 110℃; for 12h;A 10%
B 6%
Beta-pinene
177698-19-0

Beta-pinene

A

nopinone
24903-95-5

nopinone

B

pinocarvone
16812-40-1

pinocarvone

C

myrtenol
515-00-4

myrtenol

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; titanium(IV) oxide In acetonitrile for 6h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Beta-pinene
177698-19-0

Beta-pinene

A

pinocarvone
16812-40-1

pinocarvone

B

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; sodium acetate; sodium chloride; palladium dichloride 1.) AcOH, reflux; 2.) CH3CN, irradiation λ=366 nm; Yield given. Multistep reaction. Yields of byproduct given;
Beta-pinene
177698-19-0

Beta-pinene

A

myrtenyl hydroperoxide
58434-29-0

myrtenyl hydroperoxide

7,7-Dimethyl-3-oxatricyclo<4.1.1.02,4>octane-2-methanol
105815-51-8

7,7-Dimethyl-3-oxatricyclo<4.1.1.02,4>octane-2-methanol

C

myrtenol
515-00-4

myrtenol

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; 5,15,10,20-tetraphenylporphyrin; Ti(O-t-Bu) In chloroform-d1 at 0℃; for 28h; Product distribution; Irradiation; other catalysts;A 43 % Spectr.
B 23 % Spectr.
C 16 % Spectr.
D 18 % Spectr.
With oxygen; 5,15,10,20-tetraphenylporphyrin; Ti(O-t-Bu) In chloroform-d1 at 0℃; for 28h; Irradiation;A 43 % Spectr.
B 23 % Spectr.
C 16 % Spectr.
D 18 % Spectr.

A

pinocarvone
16812-40-1

pinocarvone

6,6-Dimethylspirobicyclo<3.1.1>heptan-3-ol-2,2'-oxirane
33081-46-8

6,6-Dimethylspirobicyclo<3.1.1>heptan-3-ol-2,2'-oxirane

C

3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one
28664-04-2

3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; 5,15,10,20-tetraphenylporphyrin; titanium(IV) isopropylate In dichloromethane at 0℃; for 20h; Irradiation;A 5 % Spectr.
B 81 % Spectr.
C 9 % Spectr.
D 3 % Spectr.

A

pinocarvone
16812-40-1

pinocarvone

6,6-Dimethylspirobicyclo<3.1.1>heptan-3-ol-2,2'-oxirane
33081-46-8

6,6-Dimethylspirobicyclo<3.1.1>heptan-3-ol-2,2'-oxirane

C

3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one
28664-04-2

3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one

(1α,2β,4β,6α)-2,2,7-trimethyl-3-oxatricyclo[4.1.1.02,4]octane
32162-27-9

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

E

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; thiamine diphosphate; bis(acetylacetonate)oxovanadium In dichloromethane at 0℃; Product distribution; Irradiation; other catalysts;A 8 % Spectr.
B 46 % Spectr.
C 28 % Spectr.
D 10 % Spectr.
E 8 % Spectr.
myrtenyl hydroperoxide
58434-29-0

myrtenyl hydroperoxide

A

pinocarvone
16812-40-1

pinocarvone

C

myrtenol
515-00-4

myrtenol

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
In hexane at 40℃; for 3528h; Product distribution; isomerization reaction;

A

pinocarvone
16812-40-1

pinocarvone

C

myrtenyl hydroperoxide
58434-29-0

myrtenyl hydroperoxide

D

myrtenol
515-00-4

myrtenol

E

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With copper acetylacetonate Product distribution; Ambient temperature; other metal compounds; other hydroperoxide;
myrtenol
515-00-4

myrtenol

A

myrtenic acid
19250-17-0

myrtenic acid

B

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With chlorine dioxide In tetrachloromethane at 50℃; for 0.75h;A 4 % Chromat.
B 41 % Chromat.
dextrorotatory myrtenol

dextrorotatory myrtenol

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
d-myrtenal;
acetic acid
64-19-7

acetic acid

myrtenol
515-00-4

myrtenol

chromic acid

chromic acid

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

B

α-pinene epoxide
1686-14-2

α-pinene epoxide

C

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene; oxygen In various solvent(s) Product distribution; Further Variations:; Reagents; Solvents; Oxidation; Irradiation;

C

α-pinene epoxide
1686-14-2

α-pinene epoxide

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene; oxygen In acetonitrile Product distribution; Further Variations:; Solvents; Oxidation; Irradiation;
Beta-pinene
177698-19-0

Beta-pinene

A

pinocarvone
16812-40-1

pinocarvone

3-hydroxy-β-pinene
1674-08-4

3-hydroxy-β-pinene

C

myrtenol
515-00-4

myrtenol

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; Co-Fe3O4 at 60℃; under 760.051 Torr; for 7h; Product distribution; Further Variations:; Catalysts;
Beta-pinene
177698-19-0

Beta-pinene

B

myrtenol
515-00-4

myrtenol

C

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With 2,6-dimethylpyridine; oxygen; rose bengal; acetic anhydride In methanol at 20℃; for 4h; UV-irradiation;
Beta-pinene
177698-19-0

Beta-pinene

A

myrtenol
515-00-4

myrtenol

B

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; rose bengal In N,N-dimethyl-formamide at 20℃; for 4h; UV-irradiation;
Beta-pinene
177698-19-0

Beta-pinene

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen; rose bengal; acetic anhydride In methanol at 20℃; for 4h; UV-irradiation;
Conditions
ConditionsYield
With oxygen; rose bengal In N,N-dimethyl-formamide at 20℃; for 4h; UV-irradiation;
With dihydrogen peroxide In acetonitrile at 60℃; for 24h; Temperature;A 41 %Chromat.
B 13 %Chromat.
C 17 %Chromat.
D 11 %Chromat.
Conditions
ConditionsYield
With 2,6-dimethylpyridine; oxygen; rose bengal; acetic anhydride In methanol at 20℃; for 4h; UV-irradiation;
Beta-pinene
177698-19-0

Beta-pinene

A

pinocarvone
16812-40-1

pinocarvone

trans-pinocarveol

trans-pinocarveol

C

myrtenol
515-00-4

myrtenol

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen at 60℃; under 760.051 Torr; for 6h; Neat (no solvent);

A

verbenone
80-57-9

verbenone

C

pinocarvone
16812-40-1

pinocarvone

trans-pinocarveol

trans-pinocarveol

E

α-pinene epoxide
1686-14-2

α-pinene epoxide

F

myrtenol
515-00-4

myrtenol

G

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen at 60℃; under 760.051 Torr; for 6h; Neat (no solvent);

A

verbenone
80-57-9

verbenone

C

pinocarvone
16812-40-1

pinocarvone

trans-pinocarveol

trans-pinocarveol

E

myrtenol
515-00-4

myrtenol

F

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With oxygen at 60℃; under 3800.26 Torr; for 3.5h; Neat (no solvent); Autoclave;

A

pinocarvone
16812-40-1

pinocarvone

C

pinocarveyl hydroperoxide
22321-84-2

pinocarveyl hydroperoxide

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With 6,7-bis[3-(Nε-tert-butyloxycarbonyllysine methyl ester)]-1,3,5,8-tetramethyl-2,4-divinylporphyrin immobilized in silica gel In chloroform at 20℃; for 30h; Quantum yield; Time; Irradiation;

A

pinocarvone
16812-40-1

pinocarvone

trans-pinocarveol

trans-pinocarveol

C

pinocarveyl hydroperoxide
22321-84-2

pinocarveyl hydroperoxide

D

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
With chlorophyll extract of fresh spinach leaves immobilized in silica gel In chloroform at 20℃; Reagent/catalyst; Irradiation;
(1S,2S)-1-phenyl-N2-methyl-1,2-propandiamine
130827-43-9

(1S,2S)-1-phenyl-N2-methyl-1,2-propandiamine

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

(1R,2R,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine
130827-39-3, 130857-87-3, 130857-92-0

(1R,2R,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine

Conditions
ConditionsYield
In chloroform for 24h; Ambient temperature;100%
1R,2S-N,N-dimethyl-2-phenyl-3-methyl-1,3-diaminoethane
130857-96-4

1R,2S-N,N-dimethyl-2-phenyl-3-methyl-1,3-diaminoethane

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

(1S,2S,3R,4S,5R)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine
130827-41-7, 130857-89-5, 130857-95-3

(1S,2S,3R,4S,5R)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine

Conditions
ConditionsYield
In chloroform for 24h; Ambient temperature;100%
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

6,6-dimethylbicyclo<3.3.1>heptane-2-carboxaldehyde
4764-14-1

6,6-dimethylbicyclo<3.3.1>heptane-2-carboxaldehyde

Conditions
ConditionsYield
With hydrogen; SC-1 Ni2B In methanol at 25℃; under 760 Torr; for 24h;96%
With hydrido(triphenylphosphine)copper(I) hexamer; phenylsilane In toluene for 5h; Ambient temperature;80%
acetone
67-64-1

acetone

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

4-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)-2-butanone
56933-99-4

4-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)-2-butanone

Conditions
ConditionsYield
With Pd-MgO; hydrogen at 75℃; under 3750.38 Torr; for 3h;95%
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2,2-dimethoxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene
1263208-49-6

2,2-dimethoxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
With 1-ethyl-3-methylimidazolium hydrogensulfate In methanol at 5 - 20℃; for 2h;93%
1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

C16H22O2

C16H22O2

Conditions
ConditionsYield
With ethylenediamine diacetic acid In neat (no solvent) at 20℃; for 0.5h; Knoevenagel Condensation; Green chemistry;93%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol
33829-99-1

1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Ambient temperature;92%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

(1R)-(-)-myrtenal

(1R)-(-)-myrtenal

Conditions
ConditionsYield
With pyrrolidine In methanol for 5h; Inert atmosphere; Schlenk technique;90%
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

(E)-3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)prop-2-enal
124931-24-4

(E)-3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)prop-2-enal

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Sealed tube; Inert atmosphere;
Stage #2: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran at 20℃; for 6h; Sealed tube; Inert atmosphere;
90%
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

myrtenol
515-00-4

myrtenol

Conditions
ConditionsYield
With lithium pyrrolidinoborohydride at 25℃;89%
With LiPyrrBH3 In tetrahydrofuran at 25℃; for 3h;89%
With sodium triphenyl boronhydride In tetrahydrofuran at 0℃; for 1h;100 % Chromat.
With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 60℃; for 2h; Schlenk technique; Inert atmosphere;99 %Chromat.
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

α-pinenyl bromide
22339-11-3

α-pinenyl bromide

Conditions
ConditionsYield
Stage #1: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 8h;
Stage #2: With carbon tetrabromide; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 0.5h;
84%
3,5-dimethyl-4-nitroisoxazole
1123-49-5

3,5-dimethyl-4-nitroisoxazole

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

5-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)vinyl]-3-methyl-4-nitroisoxazole

5-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)vinyl]-3-methyl-4-nitroisoxazole

Conditions
ConditionsYield
With piperidine In ethanol at 65℃; for 2h;81%
(Z)-2-cyano-3-mercapto-3-(phenylamino)acrylamide

(Z)-2-cyano-3-mercapto-3-(phenylamino)acrylamide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

(RR,RS)-5-cyano-2-(6',6'-dimethylbicyclo[3.1.1]hept-2'-en-2'-yl)-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one
884536-72-5

(RR,RS)-5-cyano-2-(6',6'-dimethylbicyclo[3.1.1]hept-2'-en-2'-yl)-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 2h; Heating;80%
4-methylthiosemicarbazide
6610-29-3

4-methylthiosemicarbazide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

C12H19N3S

C12H19N3S

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 85℃;80%
2,4-imidazolidinedione
461-72-3

2,4-imidazolidinedione

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

5-[1-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione

5-[1-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione

Conditions
ConditionsYield
With sodium acetate on alumina for 0.0333333h; microwave irradiation;76%
acetonitrile
75-05-8

acetonitrile

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

C12H17NO
324538-16-1

C12H17NO

Conditions
ConditionsYield
With [2,6-(iPr2PO)2C6H3]NiCH2CN at 20℃; for 24h; Inert atmosphere;73%
(1R,2S)-1-phenyl-N2-methyl-1,2-propandiamine
130827-42-8

(1R,2S)-1-phenyl-N2-methyl-1,2-propandiamine

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

A

(1R,2R,3S,4R,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine
130827-39-3, 130857-87-3, 130857-92-0

(1R,2R,3S,4R,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine

B

(1S,2S,3S,4R,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine
130827-39-3, 130857-87-3, 130857-92-0

(1S,2S,3S,4R,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine

Conditions
ConditionsYield
In chloroform for 24h; Ambient temperature;A 71%
B 12%
N-aminophthalamide
1875-48-5

N-aminophthalamide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

A

2,3-dihydrophthalazine-1,4-dione
1445-69-8

2,3-dihydrophthalazine-1,4-dione

B

myrtenal phthaloylhydrazone
121597-24-8

myrtenal phthaloylhydrazone

Conditions
ConditionsYield
In ethanol for 2.5h; Heating;A n/a
B 67%
formic acid
64-18-6

formic acid

Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

2-(cyclohexylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

2-(cyclohexylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 48h; Passerini Condensation; Inert atmosphere;66%
formic acid
64-18-6

formic acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

2-(tert-butylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

2-(tert-butylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 48h; Passerini Condensation; Inert atmosphere;64%
N-Boc-(tri-n-butylstannyl)dimethylamine

N-Boc-(tri-n-butylstannyl)dimethylamine

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

1,1-dimethylethyl N-methyl-N-[(bicyclo[3.3.1](4,4-dimethyl-6-formyl)heptyl)methyl] carbamate

1,1-dimethylethyl N-methyl-N-[(bicyclo[3.3.1](4,4-dimethyl-6-formyl)heptyl)methyl] carbamate

Conditions
ConditionsYield
Stage #1: N-Boc-(tri-n-butylstannyl)dimethylamine With n-butyllithium In tetrahydrofuran at -78℃; for 0.283333h; Metallation;
Stage #2: In tetrahydrofuran at -78 - -53℃; for 0.416667h; Transmetallation;
Stage #3: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde With chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; Substitution;
62%
(1S,2S)-1-phenyl-N1,N2-dimethyl-1,2-propandiamine
130857-97-5

(1S,2S)-1-phenyl-N1,N2-dimethyl-1,2-propandiamine

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

A

(1R,2R,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine
130827-41-7, 130857-89-5, 130857-95-3

(1R,2R,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine

B

(1R,2S,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine
130827-41-7, 130857-89-5, 130857-95-3

(1R,2S,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine

Conditions
ConditionsYield
In chloroform for 24h; Ambient temperature;A 60%
B 40%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-[1,3]dithiane
69460-06-6

2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-[1,3]dithiane

Conditions
ConditionsYield
With TAFF In benzene for 3h; Heating;60%
(S)-5-oxopyrrolidine-2-carbohydrazide
934-06-5

(S)-5-oxopyrrolidine-2-carbohydrazide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

N'-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylene)-5-oxopyrrolidine-2-carbohydrazide

N'-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylene)-5-oxopyrrolidine-2-carbohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In water at 20℃; for 1h;60%
formic acid
64-18-6

formic acid

p-chlorobenzylisocyanide
39546-47-9

p-chlorobenzylisocyanide

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

2-(4-chlorobenzylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

2-(4-chlorobenzylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 48h; Passerini Condensation; Inert atmosphere;57%
6,7-dimethoxy-1-cyanomethylene-1,2,3,4-tetrahydroisoquinoline
51054-41-2

6,7-dimethoxy-1-cyanomethylene-1,2,3,4-tetrahydroisoquinoline

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

C22H24N2O2

C22H24N2O2

Conditions
ConditionsYield
With cerium(III) chloride In acetonitrile at 20℃; for 6h;52%

564-94-3Relevant articles and documents

Aspect Cinetique des Substitutions Homolytiques Intramoleculaires. Decomposition de Peroxydes Insatures Derives du Pinane

Montaudon, Evelyne,Bourgeois, Marie-Josephe

, p. 9335 - 9342 (1994)

The decomposition, in dichloromethane, of β- and γ-unsaturated peroxides derived from pinane leads to transient tertiary pinanyl adduct radicals.The evolution of the reaction depends on the position of the insaturation.An intramolecular homolytic substitution gives functional pinanic epoxides in the first case; a β-scission followed by a hydrogen transfer yields functional p-menthenic peroxides in the second case.

Synthesis of Myrtenal-Based Nanocellulose/Diacylhydrazine Complexes with Antifungal Activity for Plant Protection

Cen, Bo,Duan, Wengui,Li, Baoyu,Lin, Guishan,Wang, Xiaoyu

, p. 12956 - 12965 (2021/11/17)

In search of novel bioactive compounds with excellent and broad-spectrum antifungal activity and nanopesticides with sustained releasing property, a series of novel myrtenal-based diacylhydrazines were designed, synthesized, and characterized. The preliminary bioassay showed that myrtenal-based 2-picolinyl hydrazide exhibited better or comparable antifungal activity than that of the commercial fungicides boscalid and chlorothalonil against the tested fungi. Furthermore, myrtenal-based nanocellulose was designed as a nanopesticide carrier and prepared from two biomass materials, bleached bagasse pulp and turpentine oil. Drug-loading capacities (LCs) of these carriers and sustained releasing properties of corresponding complexes were also evaluated, and the results indicated that the esterification reaction in the different solvents would affect the micromorphology of carriers, which was the important influential factor for loading or releasing drugs. To our delight, complex VIII-3 (LC = 0.32, total releasing amount/time = 99.8%/168 h) showed a macroporous framework with the drug evenly distributed across the opening network and staged drug-releasing performance that deserved further study as a nanopesticide.

Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology

Ganji, Suresh,Svensson, Fredric G.,Unelius, C. Rikard

, p. 3332 - 3337 (2020/11/30)

Herein we report the asymmetric syntheses of a number of oxygenated terpenoids that are of importance in the chemical ecology of bark beetles. These are pinocamphones, isopinocamphones, pinocarvones, and 4-thujanols (= sabinene hydrates). The camphones were synthesized from isopinocampheol, the pinocarvones from β-pinene, and the thujanols from sabinene. The NMR spectroscopic data, specific rotations, and elution orders of their stereoisomers on a chiral GC-phase (β-cyclodextrin) are also reported. This enables facile synthesis of pure compounds for biological activity studies and identification of stereoisomers in mixed natural samples.

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