CAS No.163133-43-5,4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE Suppliers

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Basic Information

Molecular Structure:
CAS No.:	163133-43-5
Name:	4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE
Article Data:	7

Formula:	C₁₈H₂₁NO₆
Molecular Weight:	347.368
Synonyms:	2-Naphthaleneaceticacid, 6-methoxy-a-methyl-,4-(nitrooxy)butyl ester, (S)-;(S)-2-(6-Methoxy-2-naphthyl)propanoic acid4-nitrooxybutyl ester;Nitronaproxen;
Density:	1.213 g/cm³
Boiling Point:	489.475 °C at 760 mmHg
Flash Point:	193.208 °C
PSA:	90.58000
LogP:	4.00680

Synthetic route

: 1395256-92-4
C21H18O4

: 22911-39-3
4-(nitrooxy)butan-1-ol

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With dmap In dichloromethane; 1,2-dichloro-ethane at 0℃;	96.8%

: 1395256-94-6
C22H20O5

: 22911-39-3
4-(nitrooxy)butan-1-ol

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With dmap In dichloromethane; 1,2-dichloro-ethane at 0℃;	92.8%

: 51091-84-0
(S)-naproxenoyl chloride

: 22911-39-3
4-(nitrooxy)butan-1-ol

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With calcium aluminosilicate In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity;	90%
With calcium carbonate In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity;	90%
In dichloromethane at 40℃; for 8.33333h; Heating / reflux;	88%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 22911-39-3
4-(nitrooxy)butan-1-ol

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 5℃; for 3h; Product distribution / selectivity;	85%

: 1198786-35-4
4-bromo-butyl (S)-2-(6-methoxy-2-naphthyl)-propanoate

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With silver nitrate In tetrahydrofuran; acetonitrile at 50℃; for 4h;	75%

: 3457-91-8
1,4-butanediol dinitrate

: 26159-34-2
Naprelan

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
In dimethyl sulfoxide for 120h;	75%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 146563-40-8
4-(nitrooxy)butyl bromide

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With potassium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 50 - 60℃; for 1.5h; Stage #2: 4-(nitrooxy)butyl bromide With potassium iodide In DMF (N,N-dimethyl-formamide) at 20℃; for 25h;	73%

: 669692-75-5
4-(nitrooxy)butyl p-toluensulfonate

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With potassium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 50 - 60℃; for 1.5h; Stage #2: 4-(nitrooxy)butyl p-toluensulfonate In DMF (N,N-dimethyl-formamide) at 20℃; for 25h;	70%

: (S)-4-hydroxybutyl-2-(6-methoxynaphtalen-2-yl) propanoate

: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetraethylammonium nitrate In dichloromethane at -70 - 20℃; for 4h;	65%

: 51091-84-0
(S)-naproxenoyl chloride

: 22911-39-3
4-(nitrooxy)butan-1-ol

A: 1262962-53-7
2-(R)-(6-methoxy-2-naphthyl)-propanoic acid 4-nitroxybutyl ester

B: 163133-43-5
naproxcinod

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity;
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity;

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Specification

The Naproxcinod, with the CAS registry number 163133-43-5, is also known as (S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl ester. It belongs to the classification codes of Cardiovascular Agents; Nitric Oxide Donors; Osteoarthritis. This chemical's molecular formula is C₁₈H₂₁NO₆ and molecular weight is 347.36. What's more, both its IUPAC name and systematic name are the same which is called 4-Nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate. Naproxcinod is a non-steroidal anti-inflammatory drug. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators, that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects.

Physical properties about Naproxcinod are: (1)ACD/LogP: 4.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.86; (4)ACD/LogD (pH 7.4): 4.86; (5)ACD/BCF (pH 5.5): 2909.01; (6)ACD/BCF (pH 7.4): 2909.01; (7)ACD/KOC (pH 5.5): 10494.05; (8)ACD/KOC (pH 7.4): 10494.05; (9)#H bond acceptors: 7; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 90.58 Å²; (13)Index of Refraction: 1.563; (14)Molar Refractivity: 93.033 cm³; (15)Molar Volume: 286.274 cm³; (16) Polarizability: 36.881×10^-24cm³; (17)Surface Tension: 45.842 dyne/cm; (18)Density: 1.213 g/cm³; (19)Flash Point: 193.208 °C; (20)Enthalpy of Vaporization: 75.58 kJ/mol; (21)Boiling Point: 489.475 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: [O-][N+](=O)OCCCCOC(=O)[C@H](c1ccc2c(c1)ccc(OC)c2)C
(2) InChI: InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3/t13-/m0/s1
(3) InChIKey: AKFJWRDCWYYTIG-ZDUSSCGKSA-N