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  • 764-59-0 Structure
  • Basic information

    1. Product Name: hex-5-enal
    2. Synonyms: hex-5-enal;5-Hexenal;Hex-5-en-1-al
    3. CAS NO:764-59-0
    4. Molecular Formula: C6H10O
    5. Molecular Weight: 98.143
    6. EINECS: 212-127-0
    7. Product Categories: N/A
    8. Mol File: 764-59-0.mol
    9. Article Data: 35
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 128℃
    3. Flash Point: 19℃
    4. Appearance: /
    5. Density: 0.817
    6. Vapor Pressure: 10.7mmHg at 25°C
    7. Refractive Index: 1.41
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: hex-5-enal(CAS DataBase Reference)
    11. NIST Chemistry Reference: hex-5-enal(764-59-0)
    12. EPA Substance Registry System: hex-5-enal(764-59-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 764-59-0(Hazardous Substances Data)

764-59-0 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 1150, 1965 DOI: 10.1021/ja01083a050

Check Digit Verification of cas no

The CAS Registry Mumber 764-59-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 4 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 764-59:
(5*7)+(4*6)+(3*4)+(2*5)+(1*9)=90
90 % 10 = 0
So 764-59-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O/c1-2-3-4-5-6-7/h2,6H,1,3-5H2

764-59-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name hex-5-enal

1.2 Other means of identification

Product number -
Other names 5-Hexenal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:764-59-0 SDS

764-59-0Synthetic route

5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
Stage #1: 5-Hexen-1-ol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h; Swern oxidation; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane at -78 - 0℃; Swern oxidation; Inert atmosphere;
100%
Stage #1: 5-Hexen-1-ol With oxalyl dichloride; dimethyl sulfoxide at -78℃; for 1h;
Stage #2: With triethylamine
100%
With (NH4)4[CuMo6O18(OH)6]·5H2O; oxygen; sodium sulfite In water; acetonitrile at 60℃; under 760.051 Torr; for 6h;95%
N,N-dimethylhexa-1,5-dien-3-amine
75712-80-0

N,N-dimethylhexa-1,5-dien-3-amine

A

hex-5-en-1-al
764-59-0

hex-5-en-1-al

B

(E)-N,N-Dimethyl-1,5-hexadien-1-amin
82574-98-9

(E)-N,N-Dimethyl-1,5-hexadien-1-amin

C

dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
at 223.5℃; for 12h;A n/a
B 95.8%
C n/a
at 160.2 - 200.1℃; Yield given. Yields of byproduct given;
With N,N-dimethyl-cyclohexanamine at 160.2 - 200.1℃; under 3 Torr; Kinetics; Thermodynamic data; Cope rearrengament, ΔH*, ΔG*, ΔS*, Ea;
5-hexenal dimethylhydrazone
88180-24-9

5-hexenal dimethylhydrazone

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether for 4h; Ambient temperature;92%
hex-5-enyl hydroperoxide
86692-87-7

hex-5-enyl hydroperoxide

A

5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

B

(+/-)-2-pentanol
6032-29-7

(+/-)-2-pentanol

C

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
In pentane for 48h; Irradiation;A 60%
B 10%
C 30%
hex-5-enyl hydroperoxide
86692-87-7

hex-5-enyl hydroperoxide

A

5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

B

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C

5-hexenyl acetate
5048-26-0

5-hexenyl acetate

Conditions
ConditionsYield
With titanium(III) chloride; acetic acid In water for 2h;A 56%
B 27%
C 17%
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With chromium(V)A 32%
B 52%
hex-5-enyl hydroperoxide
86692-87-7

hex-5-enyl hydroperoxide

A

5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

B

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
In benzene for 48h; Irradiation;A 44%
B 43%
C 13%
cyclohexane
110-82-7

cyclohexane

A

7-oxabicyclo(2.2.1)heptane
279-49-2

7-oxabicyclo(2.2.1)heptane

B

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C

cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

D

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
With tetramethylbutane; oxygen at 753℃; under 15 Torr; for 0.00555556h; Product distribution; Kinetics; Further Variations:; Temperatures;A 0.062%
B 0.195%
C 0.037%
D 0.488%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With acetic acid; sodium nitrite
3-aminocyclohexanol
6850-39-1

3-aminocyclohexanol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With acetic acid; sodium nitrite
oct-1-ene
111-66-0

oct-1-ene

cyclohexanone
108-94-1

cyclohexanone

A

cis-2-octene
7642-04-8

cis-2-octene

B

trans-2-Octene
13389-42-9

trans-2-Octene

C

hex-5-en-1-al
764-59-0

hex-5-en-1-al

D

2-octylcyclohexanone
6814-21-7

2-octylcyclohexanone

Conditions
ConditionsYield
at 40℃; im UV-Licht.Irradiation;
oct-1-ene
111-66-0

oct-1-ene

cyclohexanone
108-94-1

cyclohexanone

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
Irradiation.mit UV-Licht;
1,5-hexadiene-3-ol
924-41-4

1,5-hexadiene-3-ol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
at 410℃;
6,6-diethoxy-hex-1-ene
761-59-1

6,6-diethoxy-hex-1-ene

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
(hydrolysis);
1-(4-dimethylamino-phenyl)-hex-5-en-1-ol
92321-81-8

1-(4-dimethylamino-phenyl)-hex-5-en-1-ol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With 4-diazonio-benzenesulfonic acid betaine
bromopentene
1119-51-3

bromopentene

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
(i) Mg, Et2O, (ii) /BRN= 605384/, (iii) aq. H2SO4; Multistep reaction;
(2-hydroxy-cyclopentylmethyl)-trimethyl-ammonium; hydroxide
70592-71-1

(2-hydroxy-cyclopentylmethyl)-trimethyl-ammonium; hydroxide

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
In water at 450℃;
1,5-hexadiene-3-ol
924-41-4

1,5-hexadiene-3-ol

A

propene
187737-37-7

propene

B

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C

acrolein
107-02-8

acrolein

Conditions
ConditionsYield
under 5 Torr; Ambient temperature; Irradiation;
under 5 Torr; Thermodynamic data; Product distribution; Ambient temperature; Irradiation; energy absorb., var. pulses;
4-pentenal
2100-17-6

4-pentenal

tris(ethylenedioxyboryl)methane
59278-44-3

tris(ethylenedioxyboryl)methane

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
Yield given. Multistep reaction;
5-hexenoyl chloride
36394-07-7

5-hexenoyl chloride

hex-5-en-1-al
764-59-0

hex-5-en-1-al

trans-(3-Trimethylsilyl)-cyclohexanol
90724-75-7

trans-(3-Trimethylsilyl)-cyclohexanol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With iodosylbenzene; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide In dichloromethane for 3h; Ambient temperature;18 % Chromat.
cyclohexanone
108-94-1

cyclohexanone

isobutene
115-11-7

isobutene

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
In benzene Quantum yield; Mechanism; Irradiation; λ=300 nm;
cyclohexanone
108-94-1

cyclohexanone

A

1-penten
109-67-1

1-penten

B

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C

Cyclopentane
287-92-3

Cyclopentane

Conditions
ConditionsYield
With sulphur hexafluoride Product distribution; Quantum yield; Mechanism; Irradiation; partial pressures varied;
cyclohexanone
108-94-1

cyclohexanone

A

hex-5-en-1-al
764-59-0

hex-5-en-1-al

B

O-deuterio-hexanoic acid

O-deuterio-hexanoic acid

Conditions
ConditionsYield
With water-d2 at 19.9℃; for 0.5h; Product distribution; Irradiation; var. conditions;
cyclohexanone
108-94-1

cyclohexanone

A

hex-5-en-1-al
764-59-0

hex-5-en-1-al

B

cyclohexane-1,3-diol
504-01-8

cyclohexane-1,3-diol

C

hexanoic acid
142-62-1

hexanoic acid

Conditions
ConditionsYield
With water-d2 at 19.9℃; for 0.5h; Product distribution; Mechanism; Irradiation; var. temp., var. magnetic field intensity;A 12 % Spectr.
B 3 % Spectr.
C 10 % Spectr.
(1R,3R)-3-Tributylstannanyl-cyclohexanol
94726-46-2, 94726-47-3

(1R,3R)-3-Tributylstannanyl-cyclohexanol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With iodosylbenzene; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide In dichloromethane for 1h; Ambient temperature;74 % Chromat.
(1S,3R)-3-Tributylstannanyl-cyclohexanol
94726-46-2, 94726-47-3

(1S,3R)-3-Tributylstannanyl-cyclohexanol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
With iodosylbenzene; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide In dichloromethane for 1h; Ambient temperature;74 % Chromat.
hex-5-enyl hydroperoxide
86692-87-7

hex-5-enyl hydroperoxide

A

2-(chloromethyl)tetrahydropyran
18420-41-2, 130233-13-5, 130233-14-6

2-(chloromethyl)tetrahydropyran

B

2-vinyltetrahydrofuran
1072-60-2

2-vinyltetrahydrofuran

C

5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

D

hex-5-en-1-al
764-59-0

hex-5-en-1-al

E

5-hexenyl acetate
5048-26-0

5-hexenyl acetate

F

3-chloro-1-oxacycloheptane

3-chloro-1-oxacycloheptane

Conditions
ConditionsYield
With acetic acid; iron(II) chloride In water for 2h; Product distribution; Heating; other reagent:TiCl3/AcOH;
hex-5-enyl hydroperoxide
86692-87-7

hex-5-enyl hydroperoxide

A

5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

B

(+/-)-2-pentanol
6032-29-7

(+/-)-2-pentanol

C

hex-5-en-1-al
764-59-0

hex-5-en-1-al

D

phenol
108-95-2

phenol

Conditions
ConditionsYield
Product distribution; Irradiation; in different solvents and reaction time;
Oxo-phenyl-acetic acid hex-5-enyl ester

Oxo-phenyl-acetic acid hex-5-enyl ester

hex-5-en-1-al
764-59-0

hex-5-en-1-al

Conditions
ConditionsYield
Irradiation;
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(4S)-2-(pent-4-en-1-yl)-4-phenyloxazolidine

(4S)-2-(pent-4-en-1-yl)-4-phenyloxazolidine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane Inert atmosphere;100%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

1,7-octadien-3-ol
30385-19-4

1,7-octadien-3-ol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;99%
In tetrahydrofuran at -80.15℃; Grignard reaction;68%
In tetrahydrofuran at 0℃; Yield given;
In tetrahydrofuran at -78℃; for 0.75h;1.07 g
In tetrahydrofuran
2–(1H–pyrrol–1–yl)–5–methylaniline
59194-21-7

2–(1H–pyrrol–1–yl)–5–methylaniline

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C17H20N2

C17H20N2

Conditions
ConditionsYield
Stage #1: 2–(1H–pyrrol–1–yl)–5–methylaniline; hex-5-en-1-al In dichloromethane at -90℃; for 1h; Pictet-Spengler Synthesis; Inert atmosphere;
Stage #2: With C80H60F6N4O6PS2(1-)*H(1+)*2CH4N2O In dichloromethane at -90℃; for 23h; Pictet-Spengler Synthesis; Inert atmosphere; enantioselective reaction;
99%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(3R)-3-propionyl-4-benzyloxazolidin-2-one
101711-78-8, 131685-53-5

(3R)-3-propionyl-4-benzyloxazolidin-2-one

4-benzyl-3-(3-hydroxy-2-methyl-oct-7-enoyl)-oxazolidin-2-one
499992-34-6

4-benzyl-3-(3-hydroxy-2-methyl-oct-7-enoyl)-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (3R)-3-propionyl-4-benzyloxazolidin-2-one With di-n-butylboryl trifluoromethanesulfonate; triethylamine In dichloromethane at -78 - 0℃; for 0.5h; Aldol Addition; Inert atmosphere;
Stage #2: hex-5-en-1-al In dichloromethane at -78 - 0℃; for 2h; Aldol Addition; Inert atmosphere;
98%
Stage #1: (3R)-3-propionyl-4-benzyloxazolidin-2-one With di-n-butylboryl trifluoromethanesulfonate; triethylamine In dichloromethane at 0 - 3℃;
Stage #2: hex-5-en-1-al In dichloromethane at -78 - 0℃;
73%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(S)-methyl 6’-chloro-3’,4,4’,5-tetrahydro-2H,2’H-spiro[benzo[b][1,4] oxazepine-3,1‘-naphthalene]-7-carboxylate

(S)-methyl 6’-chloro-3’,4,4’,5-tetrahydro-2H,2’H-spiro[benzo[b][1,4] oxazepine-3,1‘-naphthalene]-7-carboxylate

methyl (S)-6'-chloro-5-(hex-5-en-1-yl)-3',4,4',5-tetrahydro-2H,2H’-spiro[benzo[b][1,4]oxazepine-3,1'-naphthalene]-7-carboxylate

methyl (S)-6'-chloro-5-(hex-5-en-1-yl)-3',4,4',5-tetrahydro-2H,2H’-spiro[benzo[b][1,4]oxazepine-3,1'-naphthalene]-7-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;98%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Inert atmosphere;98%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

methyllithium
917-54-4

methyllithium

6-heptene-2-ol
24395-10-6

6-heptene-2-ol

Conditions
ConditionsYield
In diethyl ether at -78℃;96%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

valeryl bromide
1889-26-5

valeryl bromide

(3R,4R)-3-propyl-4-(4-penten-1-yl)oxetan-2-one
1057557-86-4

(3R,4R)-3-propyl-4-(4-penten-1-yl)oxetan-2-one

Conditions
ConditionsYield
With 2Br(1-)*C41H51AlN4O2(2+); N-ethyl-N,N-diisopropylamine In dichloromethane at -70℃; for 24h; Inert atmosphere; optical yield given as %ee;96%
With 2Br(1-)*C41H51AlN4O2(2+); N-ethyl-N,N-diisopropylamine In dichloromethane at -70℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;96%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(5S)-5-phenylmorpholin-2-one
144896-92-4

(5S)-5-phenylmorpholin-2-one

(2R,6R,8S,12S)-1-aza-10-oxo-12-phenyltricyclo<6.4.01,8.02,6>dodecan-9-one

(2R,6R,8S,12S)-1-aza-10-oxo-12-phenyltricyclo<6.4.01,8.02,6>dodecan-9-one

Conditions
ConditionsYield
With molecular sieve In benzene for 3h; Heating; other substrates, toluene as solvens, stereochemistry;95%
With molecular sieve In benzene for 3h; Heating;95%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

2-But-3-enyl-4-isopropyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one
189134-35-8

2-But-3-enyl-4-isopropyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one

(4R,5S)-2-But-3-enyl-5-(1-hydroxy-hex-5-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one

(4R,5S)-2-But-3-enyl-5-(1-hydroxy-hex-5-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at -60 - -45℃;95%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(R)-α-(hydroxymethyl)benzylhydroxylamine
321174-47-4

(R)-α-(hydroxymethyl)benzylhydroxylamine

A

(R)-2-(3aS,6aR)-Hexahydro-cyclopenta[c]isoxazol-1-yl-2-phenyl-ethanol

(R)-2-(3aS,6aR)-Hexahydro-cyclopenta[c]isoxazol-1-yl-2-phenyl-ethanol

B

(R)-2-(3aR,6aS)-Hexahydro-cyclopenta[c]isoxazol-1-yl-2-phenyl-ethanol
623582-45-6

(R)-2-(3aR,6aS)-Hexahydro-cyclopenta[c]isoxazol-1-yl-2-phenyl-ethanol

Conditions
ConditionsYield
With isopropyl alcohol; magnesium bromide In tetrahydrofuran at 65℃; for 48h;A n/a
B 95%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

hex-5-en-1-al
764-59-0

hex-5-en-1-al

2-(pent-4-en-1-yl)-1,3-dithiane
88180-26-1

2-(pent-4-en-1-yl)-1,3-dithiane

Conditions
ConditionsYield
Stage #1: 1.3-propanedithiol; hex-5-en-1-al In chloroform at 20℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In chloroform at 20℃; for 17h; Further stages.;
94%
With hydrogenchloride In chloroform at -3 - 0℃; for 5h;76.8%
With boron trifluoride diethyl etherate In dichloromethane for 1h; Ambient temperature; Yield given;
hex-5-en-1-al
764-59-0

hex-5-en-1-al

acetic anhydride
108-24-7

acetic anhydride

Acetic acid 1-acetoxy-hex-5-enyl ester
142564-04-3

Acetic acid 1-acetoxy-hex-5-enyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 0.166667h;94%
With boron trifluoride diethyl etherate In diethyl ether for 0.166667h; Ambient temperature;94%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

tert-butylamine
75-64-9

tert-butylamine

tert-butyl-hex-5-enylidene-amine

tert-butyl-hex-5-enylidene-amine

Conditions
ConditionsYield
at 20℃;94%
at 20℃; for 21h;94%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(4-nitro-benzenesulfonylmethyl)-phosphonic acid dimethyl ester

(4-nitro-benzenesulfonylmethyl)-phosphonic acid dimethyl ester

1-(hepta-1,6-diene-1-sulfonyl)-4-nitro-benzene
810690-65-4

1-(hepta-1,6-diene-1-sulfonyl)-4-nitro-benzene

Conditions
ConditionsYield
Stage #1: (4-nitro-benzenesulfonylmethyl)-phosphonic acid dimethyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h;
Stage #2: hex-5-en-1-al In tetrahydrofuran; dichloromethane at -78 - 25℃; for 1h;
93%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

(R)-2-((S)-2-nitro-1-phenylethyl)-hex-5-enal
1087041-02-8

(R)-2-((S)-2-nitro-1-phenylethyl)-hex-5-enal

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In water at 0 - 20℃; Michael condensation; enantioselective reaction;93%
3-bromo-2,3-dihydro-thiophene-1,1-dioxide
53336-42-8

3-bromo-2,3-dihydro-thiophene-1,1-dioxide

hex-5-en-1-al
764-59-0

hex-5-en-1-al

4-(1-hydroxy-5-hexenyl)-2-sulfolene
114362-81-1

4-(1-hydroxy-5-hexenyl)-2-sulfolene

Conditions
ConditionsYield
With silver; zinc In tetrahydrofuran for 5h; Ambient temperature;91.7%
With silver; zinc In tetrahydrofuran for 5h; Ambient temperature; Irradiation;91.7%
bis(cyclopentadienyl)bis(trimethylphosphane)titanium(II)

bis(cyclopentadienyl)bis(trimethylphosphane)titanium(II)

hex-5-en-1-al
764-59-0

hex-5-en-1-al

C3H4OTi(bis(cyclopentadienyl))2(CH2CH2CH2)

C3H4OTi(bis(cyclopentadienyl))2(CH2CH2CH2)

Conditions
ConditionsYield
In pentane stirred (2 h, room temp.); filtration (Celite);91%
In hexane addn. of the unsaturated ketone in hexane to the Ti compd. in hexane at room temp. and addn. of CDCl3 after 0.5 h;76%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(S)-1-(trimethylsilyl)oct-7-en-1-yn-3-ol
1005773-96-5

(S)-1-(trimethylsilyl)oct-7-en-1-yn-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With (S)-3,3'-bis(5-tert-butyl-2-methoxyphenyl)-1,1'-binaphthyl-2,2'-diol; diethylzinc In diethyl ether at 20℃; for 16h; Inert atmosphere;
Stage #2: With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #3: hex-5-en-1-al In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; optical yield given as %ee;
91%
Stage #1: trimethylsilylacetylene With (S)-3,3'-bis(5-tert-butyl-2-methoxyphenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diol; diethylzinc In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
Stage #2: With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #3: hex-5-en-1-al In tetrahydrofuran at 20℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
68%
nitromethane
75-52-5

nitromethane

hex-5-en-1-al
764-59-0

hex-5-en-1-al

(±)-1-nitrohept-6-en-2-ol
121948-45-6

(±)-1-nitrohept-6-en-2-ol

Conditions
ConditionsYield
In tetrahydrofuran; tert-butyl alcohol at 0 - 20℃;90.2%
With sodium hydroxide In ethanol for 96h; Ambient temperature;84%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

(+/-)-Oct-7-en-3-ol
88071-66-3

(+/-)-Oct-7-en-3-ol

Conditions
ConditionsYield
In tetrahydrofuran90%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

diethyl 2-oxo-2-((1S,2R)-N-camphor-10,2-sultam)-ethylphosphonate
120297-92-9

diethyl 2-oxo-2-((1S,2R)-N-camphor-10,2-sultam)-ethylphosphonate

(E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-octa-2,7-dien-1-one

(E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-octa-2,7-dien-1-one

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 0℃; Horner-Emmons reaction;90%
(azidomethyl)tri-n-butylstannane

(azidomethyl)tri-n-butylstannane

hex-5-en-1-al
764-59-0

hex-5-en-1-al

(C4H9)3SnCH2NCH(CH2)3CHCH2

(C4H9)3SnCH2NCH(CH2)3CHCH2

Conditions
ConditionsYield
With triphenylphosphine In benzene byproducts: OP(C6H5)3;90%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

3-(3,4-methylenedioxyphenyl)-3-oxopropionic acid methyl ester
54011-33-5

3-(3,4-methylenedioxyphenyl)-3-oxopropionic acid methyl ester

methyl (E)-2-(benzo[d][1,3]dioxole-5-carbonyl)octa-2,7-dienoate

methyl (E)-2-(benzo[d][1,3]dioxole-5-carbonyl)octa-2,7-dienoate

Conditions
ConditionsYield
With piperidine; acetic acid; lithium bromide In dichloromethane at 20 - 40℃; for 12h; Sealed tube; Inert atmosphere; Molecular sieve;90%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

5-aminopenta-1,2-diene
5558-11-2

5-aminopenta-1,2-diene

N-(penta-3,4-dien-1-yl)hex-5-en-1-amine
1417504-16-5

N-(penta-3,4-dien-1-yl)hex-5-en-1-amine

Conditions
ConditionsYield
Stage #1: hex-5-en-1-al; 5-aminopenta-1,2-diene In ethanol at 20 - 25℃; for 2h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In ethanol at 0℃; for 4h; Inert atmosphere;
88%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(3R)-3-propionyl-4-benzyloxazolidin-2-one
101711-78-8, 131685-53-5

(3R)-3-propionyl-4-benzyloxazolidin-2-one

(R)-4-Benzyl-3-(3-hydroxy-2-methyl-oct-7-enoyl)-oxazolidin-2-one

(R)-4-Benzyl-3-(3-hydroxy-2-methyl-oct-7-enoyl)-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (3R)-3-propionyl-4-benzyloxazolidin-2-one With di-n-butylboryl trifluoromethanesulfonate; triethylamine In dichloromethane at -78℃;
Stage #2: hex-5-en-1-al In dichloromethane at -78℃;
87%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

phenylacetylene
536-74-3

phenylacetylene

(R)-1-phenyloct-7-en-1-yn-3-ol
216961-99-8

(R)-1-phenyloct-7-en-1-yn-3-ol

Conditions
ConditionsYield
Stage #1: phenylacetylene With diethylzinc In toluene for 4h; Inert atmosphere; Reflux;
Stage #2: With titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol In touene; diethyl ether at 20℃; for 1h; Inert atmosphere;
Stage #3: hex-5-en-1-al In diethyl ether; toluene at 20℃; for 2h; Inert atmosphere; optical yield given as %ee;
87%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

1-(triisopropylsilyl)butadiyne
111409-83-7

1-(triisopropylsilyl)butadiyne

(R)-1-(triisopropylsilyl)deca-9-en-1,3-diyn-5-ol
1314872-17-7

(R)-1-(triisopropylsilyl)deca-9-en-1,3-diyn-5-ol

Conditions
ConditionsYield
Stage #1: 1-(triisopropylsilyl)butadiyne With diethylzinc; (S)-[1,1']-binaphthalenyl-2,2'-diol; N-cyclohexyl-cyclohexanamine In diethyl ether at 20℃; for 16h; Inert atmosphere;
Stage #2: hex-5-en-1-al With titanium(IV) isopropylate In diethyl ether for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
87%

764-59-0Relevant articles and documents

Moon,Haynes

, p. 3067 (1966)

Cerium(IV) Carboxylate Photocatalyst for Catalytic Radical Formation from Carboxylic Acids: Decarboxylative Oxygenation of Aliphatic Carboxylic Acids and Lactonization of Aromatic Carboxylic Acids

Hirosawa, Keishi,Mashima, Kazushi,Satoh, Tetsuya,Shinohara, Koichi,Shirase, Satoru,Tamaki, Sota,Tsurugi, Hayato

supporting information, (2020/03/25)

We found that in situ generated cerium(IV) carboxylate generated by mixing the precursor Ce(OtBu)4 with the corresponding carboxylic acids served as efficient photocatalysts for the direct formation of carboxyl radicals from carboxylic acids under blue light-emitting diodes (blue LEDs) irradiation and air, resulting in catalytic decarboxylative oxygenation of aliphatic carboxylic acids to give C-O bond-forming products such as aldehydes and ketones. Control experiments revealed that hexanuclear Ce(IV) carboxylate clusters initially formed in the reaction mixture and the ligand-to-metal charge transfer nature of the Ce(IV) carboxylate clusters was responsible for the high catalytic performance to transform the carboxylate ligands to the carboxyl radical. In addition, the Ce(IV) carboxylate cluster catalyzed direct lactonization of 2-isopropylbenzoic acid to produce the corresponding peroxy lactone and ?3-lactone via intramolecular 1,5-hydrogen atom transfer (1,5-HAT).

Synthesis, characterization and catalytic performance in cyclohexane transformation by Bi2O3/MCM-41 nanocomposite materials

Mozaffari, Majid,Ebadi, Amin

, p. 1643 - 1651 (2017/11/20)

The nanoparticles of Bi2O3 supported on mesoporous MCM-41 were prepared in a simple way and were well characterized. The oxidation of cyclohexane to cyclohexanol and cyclohexanone under 1 atmospheric pressure of air in the absence of any solvent and reducing agents with Bi2O3/MCM-41 nanocomposites were considered. These nanoparticles of Bi2O3 supported on mesoporous MCM-41 were found to be the very effective catalysts for cyclohexane oxidation with air in a temperature range of 280–370 ?C. The influences of reaction temperature, the loading amount of Bi2O3 and space velocity on the oxidation of cyclohexane were also studied, and optimized conditions were investigated.

Facile photochemical transformation of alkyl aryl selenides to the corresponding carbonyl compounds by molecular oxygen: Use of selenides as masked carbonyl groups

Hyugano, Takeshi,Liu, Suyou,Ouchi, Akihiko

supporting information; scheme or table, p. 8861 - 8866 (2009/04/05)

(Chemical Equation Presented) Alkyl aryl selenides with and without functional groups on the alkyl group were transformed efficiently into the corresponding carbonyl compounds, particulary primary alkyl aryl selenides in good yields, by a simple photolysis in the presence of air or oxygen. This transformation can be conducted without protection of functional groups. The yield of carbonyl compounds was much affected by the solvent viscosity, reaction temperature, concentration of dissolved oxygen in the solvents, wavelength of light, and structure of the aryl substituents. The present study indicates that aryl selenides can be considered as a masked carbonyl group that can be easily converted to a carbonyl group by very mild reaction conditions even in the presence of various unprotected functional groups. Therefore, this functional group transformation can be used as an important tool in organic synthesis due to its simplicity and mild reaction condition.

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