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14309-57-0 Usage

Chemical Properties

3-Nonen-2-one has an agreeable, fruity odor.

Uses

3-Nonen-2-one is a useful organic building block.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 4973, 1980 DOI: 10.1021/ja00535a026Tetrahedron Letters, 24, p. 4825, 1983 DOI: 10.1016/S0040-4039(00)94017-6

Check Digit Verification of cas no

The CAS Registry Mumber 14309-57-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,3,0 and 9 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 14309-57:
(7*1)+(6*4)+(5*3)+(4*0)+(3*9)+(2*5)+(1*7)=90
90 % 10 = 0
So 14309-57-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H16O/c1-3-4-5-6-7-8-9(2)10/h7-8H,3-6H2,1-2H3/b8-7-

14309-57-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A19084)  3-Nonen-2-one, 96%   

  • 14309-57-0

  • 10g

  • 226.0CNY

  • Detail
  • Alfa Aesar

  • (A19084)  3-Nonen-2-one, 96%   

  • 14309-57-0

  • 50g

  • 682.0CNY

  • Detail
  • Alfa Aesar

  • (A19084)  3-Nonen-2-one, 96%   

  • 14309-57-0

  • 250g

  • 2898.0CNY

  • Detail

14309-57-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Nonen-2-one

1.2 Other means of identification

Product number -
Other names FEMA 3955

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:14309-57-0 SDS

14309-57-0Synthetic route

oxime of 3-nonen-2-one

oxime of 3-nonen-2-one

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane for 1.5h; Heating;93%
dimethyl (2-oxopropyl)phosphonate
4202-14-6

dimethyl (2-oxopropyl)phosphonate

hexanal
66-25-1

hexanal

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water for 12h;82%
(3E,5E)-nona-3,5-dien-2-one
80387-31-1

(3E,5E)-nona-3,5-dien-2-one

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With <(But2PH)PdPBut2>2 pretreated with O2; hydrogen In tetrahydrofuran for 1.5h; Ambient temperature;59%
hexanal
66-25-1

hexanal

acetone
67-64-1

acetone

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With sodium hydroxide
With piperidine; acetic acid
With L-proline In water at 20℃; Aldol condensation;
2-acetoxy-non-2-ene
57374-31-9

2-acetoxy-non-2-ene

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With potassium acetate; acetic acid
1-Heptene
592-76-7

1-Heptene

acetic anhydride
108-24-7

acetic anhydride

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With zinc(II) chloride
pentanal
110-62-3

pentanal

acetone
67-64-1

acetone

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
(i) aq. NaOH, (ii) H2SO4; Multistep reaction;
(+/-)-δ-decanolactone
705-86-2

(+/-)-δ-decanolactone

A

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

B

2,4-nonanedione
6175-23-1

2,4-nonanedione

C

4-hydroxy-2-nonanone
1038622-41-1

4-hydroxy-2-nonanone

D

2-phenylethanol
60-12-8

2-phenylethanol

E

nonane-2,4-diol
91525-87-0

nonane-2,4-diol

F

hexanal
66-25-1

hexanal

Conditions
ConditionsYield
at 25℃; for 72h; Product distribution; Fusarium solani; degradative patways of alkano-δ-lactones by fungus Fusarium solani;
1-Heptene
592-76-7

1-Heptene

acetyl chloride
75-36-5

acetyl chloride

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
With tetraethylammonium chloride In dichloromethane at -10 - -5℃; electrolysis (undivided cell, Al-anode, Cu-cathode);23 % Chromat.
hexanal
66-25-1

hexanal

acetone
67-64-1

acetone

A

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

B

(4S)-4-hydroxynonan-2-one
102368-24-1

(4S)-4-hydroxynonan-2-one

C

(R)-4-hydroxyl-2-nonenone

(R)-4-hydroxyl-2-nonenone

Conditions
ConditionsYield
Stage #1: acetone With L-proline In N,N-dimethyl-formamide at 10℃; for 0.5h; Aldol Addition; Sealed tube;
Stage #2: hexanal In N,N-dimethyl-formamide at 10℃; for 48h; Concentration; Solvent; Sealed tube; enantioselective reaction;
A 72 %Spectr.
B 22 %Spectr.
C n/a
hexanal
66-25-1

hexanal

acetone
67-64-1

acetone

A

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

B

C13H26O2

C13H26O2

C

(4S)-4-hydroxynonan-2-one
102368-24-1

(4S)-4-hydroxynonan-2-one

D

(R)-4-hydroxyl-2-nonenone

(R)-4-hydroxyl-2-nonenone

Conditions
ConditionsYield
Stage #1: acetone With L-proline In N,N-dimethyl-formamide at 10℃; for 0.5h; Aldol Addition; Sealed tube;
Stage #2: hexanal In N,N-dimethyl-formamide at 10℃; for 48h; Concentration; Sealed tube; enantioselective reaction;
A 13 %Spectr.
B 30 %Spectr.
C 34 %Spectr.
D n/a
hexanal
66-25-1

hexanal

1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Conditions
ConditionsYield
In dichloromethane at 80℃; for 19h; Wittig Olefination; Inert atmosphere; Sealed tube;
In tetrahydrofuran for 48h; Inert atmosphere; Reflux;
hexanal
66-25-1

hexanal

isopropyl alcohol
67-63-0

isopropyl alcohol

A

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

B

2-(n-butyl)-2-octenal
64935-38-2, 99915-14-7, 13019-16-4

2-(n-butyl)-2-octenal

C

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hafnium based tannic acid catalyst at 100℃; for 10h; Meerwein-Ponndorf-Verley Reduction; Sealed tube;A n/a
B n/a
C 65.5 %Chromat.
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

phenylboronic acid
98-80-6

phenylboronic acid

(4S)-4-phenylnonan-2-one
501919-45-5

(4S)-4-phenylnonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (R,R)-1,4-dimethyl-2,5-di(3',5'-di(trifluoromethyl)phenyl)bicyclo[2.2.2]octane-2,5-diene; potassium hydroxide In 1,4-dioxane; water at 20℃; for 3h; enantioselective reaction;99%
With chlorobis(ethylene)rhodium(I) dimer; C41H24F12O2P2; potassium hydroxide In water; toluene at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; enantioselective reaction;99%
With chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-2,6-dimethylphenyl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate; potassium hydroxide In 1,4-dioxane; water at 50℃; for 12h; optical yield given as %ee; enantioselective reaction;97%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

2-(2-oxopropyl)heptanenitrile

2-(2-oxopropyl)heptanenitrile

Conditions
ConditionsYield
With water; caesium carbonate In 1,4-dioxane for 3h; Inert atmosphere; Reflux; regioselective reaction;99%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

phenylboronic acid
98-80-6

phenylboronic acid

(S)-3-phenylnonan-2-one

(S)-3-phenylnonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (R,R)-1,4-dimethyl-2,5-di(3',5'-di(trifluoromethyl)phenyl)bicyclo[2.2.2]octane-2,5-diene; potassium hydroxide In methanol; dichloromethane at 30℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

phenylboronic acid
98-80-6

phenylboronic acid

(4R)-4-phenylnonan-2-one
435269-67-3

(4R)-4-phenylnonan-2-one

Conditions
ConditionsYield
With BF4(1-)*C68H44N2O4P2Rh(1+); water; potassium hydroxide In 1,4-dioxane at 60℃; for 1h; Anaerobic conditions; Combinatorial reaction / High throughput screening (HTS); optical yield given as %ee; enantioselective reaction;99%
With chlorobis(ethylene)rhodium(I) dimer; (R)-[6,6'-bis(bis(3,5-di(trifluoromethyl)phenyl)phosphino)-2,2',3,3'-tetrahydro-5,5'-bibenzo[b][1,4]dioxine]; potassium hydroxide In water; toluene at 20℃; for 60h; Hayashi-Miyaura reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;92%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

(S)-4-(3-chlorophenyl)nonan-2-one
1346758-83-5

(S)-4-(3-chlorophenyl)nonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,1'-(1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene-2,5-diyl)dinaphthalene; triethylamine In ethanol at 20℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-trifluoromethylphenylboronic acid
128796-39-4

4-trifluoromethylphenylboronic acid

(S)-4-(4-(trifluoromethyl)phenyl)nonan-2-one

(S)-4-(4-(trifluoromethyl)phenyl)nonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,1'-(1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene-2,5-diyl)dinaphthalene; triethylamine In ethanol at 20℃; for 72h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

(S)-4-p-tolylnonan-2-one

(S)-4-p-tolylnonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,1'-(1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene-2,5-diyl)dinaphthalene; triethylamine In ethanol at 20℃; for 29h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

(S)-4-(4-chlorophenyl)nonan-2-one
1346758-81-3

(S)-4-(4-chlorophenyl)nonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,1'-(1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene-2,5-diyl)dinaphthalene; triethylamine In ethanol at 20℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
bis(pinacolato)diborane

bis(pinacolato)diborane

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nonan-2-one
1293289-38-9

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nonan-2-one

Conditions
ConditionsYield
With picoline; copper(ll) sulfate pentahydrate In water at 20℃;98%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

C11H15BNO4(1-)*Li(1+)

C11H15BNO4(1-)*Li(1+)

C15H23NO2

C15H23NO2

Conditions
ConditionsYield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In 1,4-dioxane at 95℃; for 16h; enantioselective reaction;97%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

bis(phenylsulfonyl)methane
3406-02-8

bis(phenylsulfonyl)methane

R-4-(bis(phenylsulfonyl)methyl)nonan-2-one
1266679-13-3

R-4-(bis(phenylsulfonyl)methyl)nonan-2-one

Conditions
ConditionsYield
With 9-epi-9-amino-9-deoxyquinine; benzoic acid In 1,4-dioxane at 35℃; for 48h; Michael condensation; optical yield given as %ee; enantioselective reaction;97%
indole
120-72-9

indole

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-(1H-indol-3-yl)nonan-2-one

4-(1H-indol-3-yl)nonan-2-one

Conditions
ConditionsYield
With tin(II) chloride dihdyrate In isopropyl alcohol at 20℃; for 96h; conjugated Friedel-Crafts alkylation;96%
With [Cp2Hf2(H2O)6(μ2-OH)2(OSO2C4F9)4·4H2O·2THF] In acetonitrile at 20℃; for 3h; Reagent/catalyst; Michael Addition;94%
With 3 In acetonitrile at 20℃;87%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

C23H28O

C23H28O

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 1h;96%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

diethylzinc
557-20-0

diethylzinc

rac-4-ethylnonan-2-one
87148-00-3

rac-4-ethylnonan-2-one

Conditions
ConditionsYield
Stage #1: diethylzinc With [3-[(1R,2R)-2-(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ylidene]copper(I) bromide In diethyl ether at 25℃; for 0.25h; Inert atmosphere;
Stage #2: Non-3-en-2-on In diethyl ether at 25℃; for 1.16667h; Inert atmosphere;
Stage #3: With hydrogenchloride; water In diethyl ether
95%
triphenylboroxine
3262-89-3

triphenylboroxine

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

(4R)-4-phenylnonan-2-one
435269-67-3

(4R)-4-phenylnonan-2-one

Conditions
ConditionsYield
With potassium hydroxide; [RhCl((S,S)-2,5-dibenzylbicyclo[2.2.2]octa-2,5-diene)]2 In 1,4-dioxane; water Heating;93%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

O-p-toluenesulfonyl benzyloxyhydroxamate
64420-86-6

O-p-toluenesulfonyl benzyloxyhydroxamate

benzyl 2-acetyl-3-pentylaziridine-1-carboxylate
1096017-04-7

benzyl 2-acetyl-3-pentylaziridine-1-carboxylate

Conditions
ConditionsYield
Stage #1: Non-3-en-2-on With 1.5C13H17NO4*C20H27N3O In chloroform at 23℃; for 0.166667h;
Stage #2: O-p-toluenesulfonyl benzyloxyhydroxamate With sodium hydrogencarbonate In chloroform at 23℃; for 24h; optical yield given as %ee; enantioselective reaction;
93%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

C9H12BO3S(1-)*Li(1+)

C9H12BO3S(1-)*Li(1+)

4-thiophen-3-ylnonan-2-one

4-thiophen-3-ylnonan-2-one

Conditions
ConditionsYield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In 1,4-dioxane at 95℃; for 16h; enantioselective reaction;93%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

2-Nonanone
821-55-6

2-Nonanone

Conditions
ConditionsYield
With CuF(PPh3)3*2MeOH; bis[2-(diphenylphosphino)phenyl] ether In toluene at 25℃; for 15h; Inert atmosphere; chemoselective reaction;93%
With triethylsilane; sulfuric acid; 5%-palladium/activated carbon In tetrahydrofuran at 20℃; for 0.5h;91%
With hydrogen In ethanol; water at 25℃; under 760.051 Torr; for 12h; chemoselective reaction;88%
With hydrido(phosphonite)cobalt(I); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Sealed tube; Irradiation; Schlenk technique;63%
With (2,6-bis((diphenylphosphino)methyl)-3,5-dimethylphenyl)palladium(II) chloride; potassium carbonate; butan-1-ol for 12h; Reflux; chemoselective reaction;68 %Chromat.
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

(Z)-2-tert-butyldimethylsiloxy-2-nonene
1190963-31-5

(Z)-2-tert-butyldimethylsiloxy-2-nonene

Conditions
ConditionsYield
With palladium diacetate; tricyclohexylphosphine In toluene at 60℃; for 10h; Inert atmosphere; stereoselective reaction;92%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

phenylboronic acid
98-80-6

phenylboronic acid

(R)-4-Phenyl-nonan-2-one

(R)-4-Phenyl-nonan-2-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (R)-[6,6'-bis(bis(3,5-di(trifluoromethyl)phenyl)phosphino)-2,2',3,3'-tetrahydro-5,5'-bibenzo[b][1,4]dioxine]; potassium hydroxide In water; toluene at 20℃; for 18h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;92%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

rac-(R,S)-3,4-dibromononan-2-one

rac-(R,S)-3,4-dibromononan-2-one

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(dimethylamino)ethyl)thiourea In dichloromethane at 22℃; for 3h; optical yield given as %de; diastereospecific reaction;92%
1-methylindole
603-76-9

1-methylindole

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-(1-methyl-1H-3-indolyl)-2-nonanone
1404369-00-1

4-(1-methyl-1H-3-indolyl)-2-nonanone

Conditions
ConditionsYield
With [Cp2Hf2(H2O)6(μ2-OH)2(OSO2C4F9)4·4H2O·2THF] In acetonitrile at 20℃; for 3h; Reagent/catalyst; Michael Addition;92%
With 3 In acetonitrile at 20℃;82%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

Cumene hydroperoxide
80-15-9

Cumene hydroperoxide

A

C18H28O3
1037806-80-6

C18H28O3

B

1-((2S,3R)-3-pentyloxiran-2-yl)ethanone

1-((2S,3R)-3-pentyloxiran-2-yl)ethanone

Conditions
ConditionsYield
With 9-epi-9-amino-9-deoxyquinine; trifluoroacetic acid In toluene at 23℃; for 72h; optical yield given as %ee; enantioselective reaction;A n/a
B 91%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

C13H28OSi2
1174908-09-8

C13H28OSi2

C20H38OSi
1008534-00-6

C20H38OSi

Conditions
ConditionsYield
With [Rh(OH)(R)-binap]2 In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;91%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-(2-methyl-1H-3-indolyl)-2-nonanone
1455513-12-8

4-(2-methyl-1H-3-indolyl)-2-nonanone

Conditions
ConditionsYield
With [Cp2Hf2(H2O)6(μ2-OH)2(OSO2C4F9)4·4H2O·2THF] In acetonitrile at 20℃; for 3h; Reagent/catalyst; Michael Addition;91%
With 3 In acetonitrile at 20℃;82%
NH-pyrazole
288-13-1

NH-pyrazole

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

4-(1H-pyrazol-1-yl)nonan-2-one

4-(1H-pyrazol-1-yl)nonan-2-one

Conditions
ConditionsYield
With caesium carbonate In 1,4-dioxane at 105℃; for 12h; Schlenk technique;91%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

BuMnCl
88626-90-8

BuMnCl

4-Butyl-nonan-2-one
125408-48-2

4-Butyl-nonan-2-one

Conditions
ConditionsYield
copper(l) chloride In tetrahydrofuran at 0℃; for 4h;90%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

Non-3-en-2-on
14309-57-0

Non-3-en-2-on

A

1-(3-pentyloxiran-2-yl)ethanone
90646-63-2, 102368-23-0, 102490-11-9

1-(3-pentyloxiran-2-yl)ethanone

C13H26O3

C13H26O3

Conditions
ConditionsYield
With trifluoroacetic acid In decane; toluene at 23℃; for 4h; optical yield given as %ee; enantioselective reaction;A n/a
B 90%
Non-3-en-2-on
14309-57-0

Non-3-en-2-on

lithium 5-methyl-2-furyltriolborate

lithium 5-methyl-2-furyltriolborate

4-(5-methyl-2-furanyl)-2-nonanone

4-(5-methyl-2-furanyl)-2-nonanone

Conditions
ConditionsYield
Stage #1: lithium 5-methyl-2-furyltriolborate With bis(norbornadiene)rhodium(l)tetrafluoroborate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In 1,4-dioxane; water at 20℃; for 0.5h; Inert atmosphere;
Stage #2: Non-3-en-2-on In 1,4-dioxane; water at 30℃; for 20h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
90%

14309-57-0Relevant articles and documents

Asymmetric synthesis of 9-alkyl tetrahydroxanthenones: Via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

Gao, Yu-Qi,Hou, Yi,Chen, Junhan,Zhen, Yanxia,Xu, Dongyang,Zhang, Hongli,Wei, Hongbo,Xie, Weiqing

supporting information, p. 348 - 354 (2021/01/29)

A tandem asymmetric Michael-addition/cyclization of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters catalyzed by chiral phosphoric acid is presented. This protocol provides a facile approach for the construction of enantioenriched 9-alkyl tetrahydroxanthenones, an ubiquitous framework found in a number of natural products and pharmaceutical molecules, in high yields with good to high enantioselectivities. This journal is

Activation of Chiral (Salen)AlCl Complex by Phosphorane for Highly Enantioselective Cyanosilylation of Ketones and Enones

Zeng, Xing-Ping,Cao, Zhong-Yan,Wang, Xin,Chen, Long,Zhou, Feng,Zhu, Feng,Wang, Cui-Hong,Zhou, Jian

supporting information, p. 416 - 425 (2016/01/25)

Phosphoranes 2 are identified as a class of effective Lewis bases to activate chiral (salen)AlCl complex 1 to enhance its electrophilicity. Accordingly, a three-component catalyst system consisting of complex 1, phosphorane 2e, and Ph3PO is developed as a powerful tool for asymmetric ketone cyanosilylation. In particular, an unprecedented highly enantioselective cyanosilylation of linear aliphatic ketones is achieved. A tandem Wittig-cyanosilylation sequence starting from phosphorane 2a and enals 10 is further achieved, which internally utilizes the Ph3PO byproduct and remaining phosphorane 2a as cocatalysts for cyanosilylation of α,β,γ,δ-unsaturated enones, providing atom-efficient access to valuable chiral conjugated dienes and enynes. The high efficiency of the cyanosilylation originates from orthogonal activation of both (salen)AlCl complex 1 and cyanotrimethylsilane by the phosphorane and Ph3PO, respectively. This mechanistic insight is supported by NMR, MS, and ReactIR analyses and DFT calculations. Furthermore, the formation of charged complexes through the activation of chiral complex 1 by phosphorane 2a is confirmed by electrical conductivity experiments.

Control of aldol reaction pathways of enolizable aldehydes in an aqueous environment with a hyperbranched polymeric catalyst

Chi, Yonggui,Scroggins, Steven T.,Boz, Emine,Fre Chet, Jean M. J.

supporting information; experimental part, p. 17287 - 17289 (2009/07/11)

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