Product Name

  • Name

    Cetilistat

  • EINECS 1308068-626-2
  • CAS No. 282526-98-1
  • Article Data11
  • CAS DataBase
  • Density 1.027 g/cm3
  • Solubility
  • Melting Point 72.0 to 76.0 °C
  • Formula C25H39NO3
  • Boiling Point 509.671 °C at 760 mmHg
  • Molecular Weight 401.59
  • Flash Point 158.925 °C
  • Transport Information
  • Appearance Off-white cryst.
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 282526-98-1 (Cetilistat)
  • Hazard Symbols
  • Synonyms 2-(Hexadecyloxy)-6-methyl-4H-3,1-benzoxazin-4-one;
  • PSA 52.33000
  • LogP 7.35650

Synthetic route

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid
890655-08-0

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Solvent; Reagent/catalyst;96.5%
With 1,1'-carbonyldiimidazole In dichloromethane Reagent/catalyst;92%
With pyridine; chloroformic acid ethyl ester at 0 - 10℃; for 1h; Reagent/catalyst; Concentration;85.5%
hexadecanyl p-trifluoromethylsulfonate

hexadecanyl p-trifluoromethylsulfonate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With triethylamine In dichloromethane Cooling with ice; Reflux;90%
hexadecyl-2-iodo-5-methylbenzoyl-carbamate

hexadecyl-2-iodo-5-methylbenzoyl-carbamate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With copper(l) iodide; calcium chloride In 1,4-dioxane for 3h; Inert atmosphere; Reflux;81%
hexadecyl-2-bromo-5-methylbenzoyl-carbamate

hexadecyl-2-bromo-5-methylbenzoyl-carbamate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With magnesium sulfate; copper(I) bromide In toluene for 3h; Inert atmosphere; Reflux;71%
2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid
890655-08-0

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With pyridine In ice-water
1-Hexadecanol
36653-82-4

1-Hexadecanol

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 3 h / 20 °C
2: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: acetonitrile / 2.5 h / 25 - 65 °C
2.1: triethylamine / 7 h / 25 - 90 °C
3.1: pyridine / dichloromethane / 0.17 h / 25 - 30 °C
3.2: 4 h / 0 - 35 °C
View Scheme
cetyl chloroformate
26272-90-2

cetyl chloroformate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 4 h / 20 °C / Reflux
2: copper(l) iodide; calcium chloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: periodic acid; chromium(VI) oxide; acetic anhydride / acetonitrile / 1.5 h / 0 - 20 °C
3: copper(l) iodide; calcium chloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: periodic acid; chromium(VI) oxide; acetic anhydride / acetonitrile / 1.5 h / 0 - 20 °C
3: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
Kohlensaeure-di-n-hexadecylester
13784-52-6

Kohlensaeure-di-n-hexadecylester

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap / dichloromethane / 18 h / 20 °C
2: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
hexadecyl-2-bromo-5-methylbenzyl-carbamate

hexadecyl-2-bromo-5-methylbenzyl-carbamate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: periodic acid; chromium(VI) oxide; acetic anhydride / acetonitrile / 1.5 h / 0 - 20 °C
2: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium carbonate / tetrahydrofuran; water
2: 1,1'-carbonyldiimidazole / dichloromethane
View Scheme
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / 20 °C
2: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling with ice
3: lithium carbonate / tetrahydrofuran; water
4: 1,1'-carbonyldiimidazole / dichloromethane
View Scheme
2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate

2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling with ice
2: lithium carbonate / tetrahydrofuran; water
3: 1,1'-carbonyldiimidazole / dichloromethane
View Scheme
2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

Conditions
ConditionsYield
In methanol; dichloromethane at 40℃; for 5h; Solvent; Temperature; Reflux;98.1%

Cetilistat Specification

The Cetilistat is an organic compound with the formula C25H39NO3. The IUPAC name of this chemical is 2-hexadecoxy-6-methyl-3,1-benzoxazin-4-one. With the CAS registry number 282526-98-1, it is also named as 4H-3,1-benzoxazin-4-one, 2-(hexadecyloxy)-6-methyl-. The product's classification code is Treatment of obesity. Besides, it is a drug designed to treat obesity. It acts in the same way as the older drug orlistat (Xenical) by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested.

Physical properties about Cetilistat are: (1)ACD/LogP: 9.74; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 4; (4)#Freely Rotating Bonds: 16; (5)Polar Surface Area: 47.89 Å2; (6)Index of Refraction: 1.521; (7)Molar Refractivity: 118.983 cm3; (8)Molar Volume: 391.042 cm3; (9)Polarizability: 47.168×10-24cm3; (10)Surface Tension: 36.133 dyne/cm; (11)Density: 1.027 g/cm3; (12)Flash Point: 158.925 °C; (13)Enthalpy of Vaporization: 78.026 kJ/mol; (14)Boiling Point: 509.671 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2OC(=N/c1c2cc(cc1)C)\OCCCCCCCCCCCCCCCC
(2)InChI: InChI=1/C25H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-28-25-26-23-18-17-21(2)20-22(23)24(27)29-25/h17-18,20H,3-16,19H2,1-2H3
(3)InChIKey: MVCQKIKWYUURMU-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C25H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-28-25-26-23-18-17-21(2)20-22(23)24(27)29-25/h17-18,20H,3-16,19H2,1-2H3
(5)Std. InChIKey: MVCQKIKWYUURMU-UHFFFAOYSA-N

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