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3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]-, also known as 1-Tosylazetidin-3-one, is a synthetic intermediate with a unique structure that features a four-membered azetidinone ring and a sulfonyl group attached to a 4-methylphenyl group. 3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]plays a significant role in the field of medicinal chemistry due to its potential applications in the synthesis of various biologically active compounds.

76543-27-6

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76543-27-6 Usage

Uses

Used in Medicinal Chemistry:
3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]is used as a synthetic intermediate for the preparation of Azaspiro[3.3]heptanes, which are valuable building blocks in medicinal chemistry. These Azaspiro[3.3]heptanes are known for their potential as therapeutic agents, particularly in the development of drugs targeting various diseases and disorders.
In the pharmaceutical industry, 3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]is used as a key component in the synthesis of complex molecular structures that can exhibit significant biological activity. The unique properties of 3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]-, such as its ability to form stable bonds and its compatibility with various chemical reactions, make it an ideal candidate for the development of novel drugs with improved efficacy and selectivity.
Furthermore, the use of 3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]in medicinal chemistry allows researchers to explore new avenues for drug discovery and design. By incorporating 3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]- into their synthetic strategies, chemists can potentially create new drug candidates with enhanced pharmacological properties, such as increased potency, better selectivity, and reduced side effects.

Check Digit Verification of cas no

The CAS Registry Mumber 76543-27-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,5,4 and 3 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 76543-27:
(7*7)+(6*6)+(5*5)+(4*4)+(3*3)+(2*2)+(1*7)=146
146 % 10 = 6
So 76543-27-6 is a valid CAS Registry Number.

76543-27-6SDS

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 N-p-tosyl-3-azetidinone

1.2 Other means of identification

Product number -
Other names 3-Azetidinone, 1-[(4-methylphenyl)sulfonyl]-

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:76543-27-6 SDS

76543-27-6Synthetic route

1-(p-Toluenesulfonyl)azetidin-3-ol
154010-96-5

1-(p-Toluenesulfonyl)azetidin-3-ol

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
With chromium(VI) oxide In acetic acid95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 20h; Heating;94%
With chromium(VI) oxide; sulfuric acid; acetic acid In water; acetone at -5 - 0℃; for 2h;74%
N-(3-Diazo-2-oxo-propyl)-4-methyl-benzenesulfonamide
72676-71-2

N-(3-Diazo-2-oxo-propyl)-4-methyl-benzenesulfonamide

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
With (CF3COCHCOCF3)2Cu In dichloromethane for 0.0833333h; Ambient temperature;80%
With styrene; copper acetylacetonate In benzene Cyclization; Heating;74%
With sulfuric acid In chloroform45%
With silver benzoate; triethylamine In methanol for 2h; Ambient temperature;40%
copper(II) hexafluoro-2,4-pentanedionate
N-(3-Diazo-2-oxo-propyl)-4-methyl-benzenesulfonamide
72676-71-2

N-(3-Diazo-2-oxo-propyl)-4-methyl-benzenesulfonamide

A

N-(4-methylbenzenesulphonyl)propanamin-2-one
54972-26-8

N-(4-methylbenzenesulphonyl)propanamin-2-one

B

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
With copper acetylacetonate; tri-n-butyl-tin hydride In benzene for 5h; Cyclization; reduction; Heating;A 31%
B 63%
3-oximino-1-(p-toluenesulfonyl) azetidine
154010-97-6

3-oximino-1-(p-toluenesulfonyl) azetidine

A

3-nitro-3-nitroso-1-(p-toluenesulfonyl)azetidine

3-nitro-3-nitroso-1-(p-toluenesulfonyl)azetidine

B

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
With nitric acid In chloroform at 10℃; for 0.916667h;A 27.5%
B n/a
N-(3-Diazo-2-oxo-propyl)-4-methyl-benzenesulfonamide
72676-71-2

N-(3-Diazo-2-oxo-propyl)-4-methyl-benzenesulfonamide

acetic acid
64-19-7

acetic acid

A

N-(3-acetoxy-2-oxopropyl)-4-methylbenzenesulphonamide
73696-30-7

N-(3-acetoxy-2-oxopropyl)-4-methylbenzenesulphonamide

B

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
for 0.0833333h; Heating; Yield given. Yields of byproduct given;
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-oxoazetidine hydrochloride salt

3-oxoazetidine hydrochloride salt

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
With triethylamine In diethyl ether Ambient temperature; Yield given;
1-(p-toluenesulfonyl)-3-(tetrahydropyran-2-yloxy)azetidine
883909-30-6

1-(p-toluenesulfonyl)-3-(tetrahydropyran-2-yloxy)azetidine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / p-toluenesulfonic acid / methanol / 20 h / 20 °C
2: 94 percent / 2-iodoxybenzoic acid / ethyl acetate / 20 h / Heating
View Scheme
2-(4-methylphenylsulfonamido)acetyl chloride
56218-62-3

2-(4-methylphenylsulfonamido)acetyl chloride

copper (II)-complex of L-lysine

copper (II)-complex of L-lysine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C
2: 40 percent / C6H5COOAg, Et3N / methanol / 2 h / Ambient temperature
View Scheme
N-Tosylglycine
1080-44-0

N-Tosylglycine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (COCl)2, DMF / CH2Cl2 / 3 h / Ambient temperature
2: tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C
3: 40 percent / C6H5COOAg, Et3N / methanol / 2 h / Ambient temperature
View Scheme
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K2CO3 / acetonitrile / 90 h / Heating
2: 98 percent / AcOH / tetrahydrofuran; H2O / 36 h / Ambient temperature
3: 74 percent / CrO3, conc. H2SO4, HOAc / acetone; H2O / 2 h / -5 - 0 °C
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

sulfate diethylamine

sulfate diethylamine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 66 percent / pyridine
2: 88 percent / imidazole / dimethylformamide / 24 h / Ambient temperature
3: 91 percent / LiH / tetrahydrofuran / 12 h / Heating
4: 98 percent / AcOH / tetrahydrofuran; H2O / 36 h / Ambient temperature
5: 74 percent / CrO3, conc. H2SO4, HOAc / acetone; H2O / 2 h / -5 - 0 °C
View Scheme
1-(p-Toluenesulfonyl)-3-(tert-butyldimethylsiloxy)azetidine
154010-95-4

1-(p-Toluenesulfonyl)-3-(tert-butyldimethylsiloxy)azetidine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / AcOH / tetrahydrofuran; H2O / 36 h / Ambient temperature
2: 74 percent / CrO3, conc. H2SO4, HOAc / acetone; H2O / 2 h / -5 - 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 83 percent / acetic acid / Heating
2: 95 percent / CrO3 / acetic acid
View Scheme
3-(p-Toluenesulfonamido)propan-2-ol 1-(p-toluenesulfonate)
154010-93-2

3-(p-Toluenesulfonamido)propan-2-ol 1-(p-toluenesulfonate)

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 88 percent / imidazole / dimethylformamide / 24 h / Ambient temperature
2: 91 percent / LiH / tetrahydrofuran / 12 h / Heating
3: 98 percent / AcOH / tetrahydrofuran; H2O / 36 h / Ambient temperature
4: 74 percent / CrO3, conc. H2SO4, HOAc / acetone; H2O / 2 h / -5 - 0 °C
View Scheme
Multi-step reaction with 4 steps
1: 88 percent / imidazole / dimethylformamide
2: 91 percent / LiH / tetrahydrofuran
3: 83 percent / acetic acid / Heating
4: 95 percent / CrO3 / acetic acid
View Scheme
3-(p-toluenesulfonamido)propane-2-ol-1-(p-toluenesulfonate) t-butyldimethylsilyl ether
154010-94-3

3-(p-toluenesulfonamido)propane-2-ol-1-(p-toluenesulfonate) t-butyldimethylsilyl ether

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / LiH / tetrahydrofuran / 12 h / Heating
2: 98 percent / AcOH / tetrahydrofuran; H2O / 36 h / Ambient temperature
3: 74 percent / CrO3, conc. H2SO4, HOAc / acetone; H2O / 2 h / -5 - 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 91 percent / LiH / tetrahydrofuran
2: 83 percent / acetic acid / Heating
3: 95 percent / CrO3 / acetic acid
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

vinyldiacetonamine

vinyldiacetonamine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 66 percent / pyridine
2: 88 percent / imidazole / dimethylformamide
3: 91 percent / LiH / tetrahydrofuran
4: 83 percent / acetic acid / Heating
5: 95 percent / CrO3 / acetic acid
View Scheme
2-(4-methylphenylsulfonamido)acetyl chloride
56218-62-3

2-(4-methylphenylsulfonamido)acetyl chloride

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
2: 80 percent / (CF3COCHCOCF3)2Cu / CH2Cl2 / 0.08 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: diethyl ether
2: 0.08 h / Heating
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 12 h / 20 °C / Schlenk technique
2: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
2.2: 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: methanesulfonic acid; silver(I) triflimide / 1,2-dichloro-ethane / 20 °C
View Scheme
3,5-dicholoropyridine N-oxide
15177-57-8

3,5-dicholoropyridine N-oxide

4-methyl-N-prop-2-ynylbenzenesulfonamide
55022-46-3

4-methyl-N-prop-2-ynylbenzenesulfonamide

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Conditions
ConditionsYield
With methanesulfonic acid; silver(I) triflimide In 1,2-dichloro-ethane at 20℃;
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

3-oximino-1-(p-toluenesulfonyl) azetidine
154010-97-6

3-oximino-1-(p-toluenesulfonyl) azetidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol for 2h; Reflux;100%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol 1.) RT, 1 h, 2.) reflux, 1 h;96%
With hydroxylamine hydrochloride; sodium acetate In methanol for 2h; Heating;90%
With hydroxylamine hydrochloride; sodium acetate In methanol for 2h; Heating;90%
With hydroxylamine Yield given;
potassium ((4-methoxyphenyl)ethynyl)trifluoroborate

potassium ((4-methoxyphenyl)ethynyl)trifluoroborate

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C19H18BF3NO4S(1-)*K(1+)

C19H18BF3NO4S(1-)*K(1+)

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In 1,4-dioxane at 60℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;98%
4-Octyne
1942-45-6

4-Octyne

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

4,5-dipropyl-1-tosyl-1,6-dihydropyridin-3(2H)-one
1372173-48-2

4,5-dipropyl-1-tosyl-1,6-dihydropyridin-3(2H)-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 6h; Inert atmosphere; regioselective reaction;96%
With bis(1,5-cyclooctadiene)nickel(0); triphenylphosphine In toluene at 20℃; for 15h; Inert atmosphere;92%
With nickel(0)(1,5-cyclooctadiene)2; triphenylphosphine In 1,4-dioxane at 110℃; for 17h; Inert atmosphere;73%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

1-(p-Toluenesulfonyl)azetidin-3-ol
154010-96-5

1-(p-Toluenesulfonyl)azetidin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 0.166667h; Ambient temperature;92%
With sodium tetrahydroborate Product distribution;
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl 2-(1-tosylazetidin-3-ylidene)acetate
1223573-28-1

ethyl 2-(1-tosylazetidin-3-ylidene)acetate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 0.25h; Inert atmosphere;92%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

potassium (2-methyl-1-buten-3-yn-4-yl)trifluoroborate

potassium (2-methyl-1-buten-3-yn-4-yl)trifluoroborate

C15H16BF3NO3S(1-)*K(1+)

C15H16BF3NO3S(1-)*K(1+)

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In 1,4-dioxane at 60℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;92%
nitromethane
75-52-5

nitromethane

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C11H14N2O5S

C11H14N2O5S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol at 25℃; for 15h;89.1%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

N-(4-methylbenzenesulphonyl)propanamin-2-one
54972-26-8

N-(4-methylbenzenesulphonyl)propanamin-2-one

Conditions
ConditionsYield
With titanium(IV) iodide In dichloromethane at 0 - 20℃; for 15h; Inert atmosphere;80%
With titanium(IV) iodide In dichloromethane at 0 - 20℃; for 15h; Inert atmosphere;18.2 mg
C16H18

C16H18

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C26H29NO3S

C26H29NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;79%
C13H14

C13H14

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C23H25NO3S

C23H25NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;79%
(5-methylhex-5-en-3-yn-1-yl)benzene
1286793-24-5

(5-methylhex-5-en-3-yn-1-yl)benzene

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C23H25NO3S

C23H25NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;78%
(6-methylhept-5-en-3-yn-1-yl)benzene
1286793-27-8

(6-methylhept-5-en-3-yn-1-yl)benzene

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C24H27NO3S

C24H27NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;78%
4,4-dimethyl-2-pentyne
999-78-0

4,4-dimethyl-2-pentyne

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

5-(tert-butyl)-4-methyl-1-tosyl-1,6-dihydropyridin-3(2H)-one
1372173-51-7

5-(tert-butyl)-4-methyl-1-tosyl-1,6-dihydropyridin-3(2H)-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 6h; Inert atmosphere; regioselective reaction;77%
C18H24

C18H24

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C28H35NO3S

C28H35NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;77%
C14H16

C14H16

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C24H27NO3S

C24H27NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;76%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

N,N-bis(p-toluenesulfonyl)-3-hydroxy-3-(3'-hydroxy-3'-azetidinyl)azetidine
220332-09-2

N,N-bis(p-toluenesulfonyl)-3-hydroxy-3-(3'-hydroxy-3'-azetidinyl)azetidine

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 25℃; for 8h;73%
potassium trifluoro(prop-1-yn-1-yl)borate

potassium trifluoro(prop-1-yn-1-yl)borate

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C13H14BF3NO3S(1-)*K(1+)

C13H14BF3NO3S(1-)*K(1+)

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In 1,4-dioxane at 60℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;70%
C18H24

C18H24

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C28H35NO3S

C28H35NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;69%
2-methyl-1-hexen-3-yne
23056-94-2

2-methyl-1-hexen-3-yne

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C17H21NO3S

C17H21NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 60h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;69%
tryptamine
61-54-1

tryptamine

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

1-tosyl-2',3',4',9'-tetrahydrospiro[azetidine-3,1'-pyrido[3,4-b]indole]
1523558-88-4

1-tosyl-2',3',4',9'-tetrahydrospiro[azetidine-3,1'-pyrido[3,4-b]indole]

Conditions
ConditionsYield
With trifluoroacetic acid In toluene at 85℃; for 18h; Pictet-Spengler Synthesis; Inert atmosphere;65%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

(3-methylbut-3-en-1-yn-1-yl)cyclohexane
908295-93-2

(3-methylbut-3-en-1-yn-1-yl)cyclohexane

C21H27NO3S

C21H27NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;65%
C11H16

C11H16

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C21H27NO3S

C21H27NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;65%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

L-tryptophan ethyl ester
7479-05-2

L-tryptophan ethyl ester

(S)-ethyl 1-tosyl-2',3',4',9'-tetrahydrospiro[azetidine-3,1'-pyrido[3,4-b]indole]-3'-carboxylate
1523558-90-8

(S)-ethyl 1-tosyl-2',3',4',9'-tetrahydrospiro[azetidine-3,1'-pyrido[3,4-b]indole]-3'-carboxylate

Conditions
ConditionsYield
With iodine In acetonitrile at 82℃; for 18h; Pictet-Spengler Synthesis; Inert atmosphere;64%
C21H26Cl2N4O3SSi
1211937-22-2

C21H26Cl2N4O3SSi

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C24H31Cl2NO3SSi
1211937-17-5

C24H31Cl2NO3SSi

Conditions
ConditionsYield
Stage #1: C21H26Cl2N4O3SSi; 1-(p-toluenesulfonyl) azetidin-3-one With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran Saturated solution;
62%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

benzaldehyde
100-52-7

benzaldehyde

A

4-hydroxy-4-phenyl-1-(p-tosylamino)butan-2-one
1241391-03-6

4-hydroxy-4-phenyl-1-(p-tosylamino)butan-2-one

B

N-(4-methylbenzenesulphonyl)propanamin-2-one
54972-26-8

N-(4-methylbenzenesulphonyl)propanamin-2-one

Conditions
ConditionsYield
With titanium(IV) iodide; titanium tetrachloride In dichloromethane at 0 - 20℃; for 15h; Mannich type reaction; Inert atmosphere;A 12%
B 61%
C16H18

C16H18

1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

C26H29NO3S

C26H29NO3S

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;54%
1-(p-toluenesulfonyl) azetidin-3-one
76543-27-6

1-(p-toluenesulfonyl) azetidin-3-one

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

3-(benzo[b]thiophen-2-yl)-1-tosylazetidin-3-ol

3-(benzo[b]thiophen-2-yl)-1-tosylazetidin-3-ol

Conditions
ConditionsYield
Stage #1: Benzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 1h; Inert atmosphere;
Stage #2: 1-(p-toluenesulfonyl) azetidin-3-one In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
45%

76543-27-6Relevant articles and documents

Gold-Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3-Sigmatropic Shift of an Initial Intermediate

Chao, Tzu-Hsuan,Chen, Mu-Jeng,Liu, Rai-Shung,Raj, Antony Sekar Kulandai,Sasane, Amit Vijay

supporting information, p. 16932 - 16938 (2020/11/30)

Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species.

Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates

Barday, Manuel,Ho, Kelvin Y. T.,Halsall, Christopher T.,A?ssa, Christophe

, p. 1756 - 1759 (2016/05/19)

The poor regioselectivity of the [4 + 2] cycloaddition of 3-azetidinones with internal alkynes bearing two alkyl substituents via nickel-catalyzed carbon-carbon activation is addressed using 1,3-enynes as substrates. The judicious choice of substitution on the enyne enables complementary access to each regioisomer of 3-hydroxy-4,5-alkyl-substituted pyridines, which are important building blocks in medicinal chemistry endeavors.

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

Ishida, Naoki,Shimamoto, Yasuhiro,Yano, Takaaki,Murakami, Masahiro

, p. 19103 - 19106 (2014/01/17)

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Thermal decomposition of 1,3,3-trinitroazetidine in the gas phase, solution, and melt

Nedel'Ko,Korsunskii,Makhova,Chukanov,Larikova,Ovchinnikov,Tartakovsky

experimental part, p. 2028 - 2034 (2011/01/09)

1,3,3-Trinitroazetidine (TNAZ) was synthesized using the alternative approach based on the transformation of 3-oximino-1-(p-toluenesulfonyl)azetidine in the reaction with nitric acid through intermediate pseudonitrol. The thermal decomposition of TNAZ in the gas phase, melt and m-dinitrobenzene solution in a wide concentration range (5-80%) was studied by manometry, volumetry, thermogravimetry, IR spectroscopy, and mass spectrometry. In the gas phase in the temperature range from 170 to 220°C the thermal decomposition proceeds according to the first-order kinetic law with the activation energy 40.5 kcal mol-1 and pre-exponential factor 1015.0 s-1. The major gaseous reaction products are N2, NO, NO2, CO2, H2O, and nitroacetaldehyde, and trace amounts of CO and HCN are formed. The rate-determining step of the process is the homolytic cleavage of the N-NO2 bond in the TNAZ molecule. In melt at 170-210 °C the thermal decomposition proceeds with the pronounced self-acceleration and the maximum reaction rates are observed at conversions 53.9-67.4%. The solid decomposition products accelerate the reaction. It is most likely that the autocatalysis of TNAZ decomposition in the liquid phase is due to the autocatalytic decomposition of 1-nitroso-3,3-dinitroazetidine, which is formed by the thermal decomposition of TNAZ. In m-dinitrobenzene TNAZ also decomposes with self-acceleration. The higher the concentration in the solution, the more pronounced the self-acceleration. Additives of picric acid moderately accelerate the thermal decomposition of TNAZ, whereas hexamethylenetetraamine additives exert a strong acceleration.

Improved synthesis of an energetic material, 1,3,3-trinitroazetidine (TNAZ) exploiting 2-iodoxy benzoic acid (IBX) as an oxidising agent

Singh, Alok,Sikder, Nirmala,Sikder, Arun K.

, p. 2560 - 2563 (2007/10/03)

Tetrahydropyranyl protected 1,3-dihalo-2-propanol reacts with p-toluene sulfonamide in the presence of K2CO3 to give corresponding N-p-tosyl-3-azetidinol. Deprotection and oxidation with iodoxy benzoic acid followed by oximation of N-p-tosyl-3-azetidinone readily affords the corresponding azetidine oxime in almost quantitative yield. The subsequent oxidative nitrolysis of oxime gives 1,3,3-trinitroazetidine (TNAZ) through a new sequence of reactions with excellent purity (> 99%) and moderate yield (40%).

Diazo decomposition in the presence of tributyltin hydride. Reduction of α-diazo carbonyl compounds

Tan, Zhongping,Qu, Zhaohui,Chen, Bei,Wang, Jianbo

, p. 7457 - 7461 (2007/10/03)

The diazo group of a series of α-diazo carbonyl compounds can be reduced to the corresponding CH2 group by Bu3SnH under Cu(acac)2-catalytic or photochemical conditions. The mechanistic aspects of this reaction were investigated in some detail, and a possible reaction pathway was discussed. (C) 2000 Elsevier Science Ltd.

Intramolecular N-H insertion of α-diazocarbonyls catalyzed by Cu(acac)2: An efficient route to derivatives of 3-oxoazetidines, 3-oxopyrrolidines and 3-oxopiperidines

Wang, Jianbo,Hou, Yihua,Wu, Peng

, p. 2277 - 2280 (2007/10/03)

Cu(acac)2 was found to be an efficient catalyst for the intramolecular N-H insertion by carbenoids. The competitive intramolecular C-H insertion by carbenoids is not a problem in the diazo decomposition reaction with Cu(acac)2 as catalyst. The reaction provided derivatives of 3-oxoazetidine, 3-oxopyrrolidine and 3-oxopiperidine in moderate to good yields.

Wolff rearrangement of diazo ketones derived from N-p-tolylsulfonyl-protected α- and β-amino acids

Wang, Jianbo,Hou, Yihua

, p. 1919 - 1923 (2007/10/03)

Diazo ketones derived from N-p-tolylsulfonyl (tosyl)-protected α- and β-amino acids have been synthesized and their diazo decomposition under standard Wolff rearrangement conditions, PhCO2Ag-Et3N-MeOH, has been investigated. It is observed that, under these conditions, several different reaction pathways, including direct carbene N-H insertion, are possible. The reaction is markedly affected by the N-protecting group, the substrate structure and solvent. For those diazo ketones derived from N-tosyl-protected β-amino acids, the diazo decomposition with anhydrous THF as solvent and PhCO2Ag dissolved in Et3N as catalyst gives the corresponding 5-substituted pyrrolidinones in excellent yields.

Synthesis of 1,3,3-Trinitroazetidine via the Oxidative Nitrolysis of N-p-Tosyl-3-azetidinone Oxime

Axenrod, T.,Watnick, C.,Yazdekhasti, H.,Dave, P. R.

, p. 1959 - 1964 (2007/10/02)

The tert-butyldimethylsilyl ether of 1,3-dibromo-2-propanol reacted with p-toluenesulfonamide in the presence of K2CO3 to give the corresponding N-p-tosyl-3-azetidinol.The same azetidinol was obtained when the similarly silyl-protected 3-(p-toluenesulfonamido)propan-2-ol 1(p-toluenesulfonate) was treated with LiH.Desilylation and oxidation of the N-p-tosyl-3-azetidinol followed by oximation readily afforded N-p-tosyl-3-azetidinone oxime.Oxidative nitrolysis of the latter intermediate delivered 1,3,3-trinitroazetidine through a new sequence of reactions.

Novel Syntheses of 1,3,3-Trinitroazetidine

Katritzky, Alan R.,Cundy, Darren J.,Chen, Jie

, p. 271 - 276 (2007/10/02)

Alternative methods for the synthesis of 1,3,3-trinitroazetidine (TNAZ) from epichlorohydrin, and benzhydrylamine have been developed.These approaches employ N-sulfonyl-3-(hydroxyimino)azetidines as penultimate intermediates and represent an improvement over previously published methods which require either diazo containing intermediates or involve low yielding procedures.Parallel methods employing N-benzhydryl- and N-benzyl-3-(hydroxyimino)azetidine were also investigated as alternate routes to TNAZ

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