Nafronyl oxalate

Base Information

• Chemical Name: Nafronyl oxalate
• CAS No.: 3200-06-4
• Molecular Formula: C24H33NO3.C2H2O4
• Molecular Weight: 473.566
• Hs Code.: 29321900
• European Community (EC) Number: 221-703-0
• NSC Number: 758462,225233
• UNII: 5ADB8D9388
• DSSTox Substance ID: DTXSID6045533
• Wikidata: Q27261749
• NCI Thesaurus Code: C87286
• ChEMBL ID: CHEMBL1439099
• Mol file: 3200-06-4.mol

Synonyms:Artocoron;Azunaftil;Di Actane;Di-Actane;Dusodril;Gévatran;LS 121;LS-121;LS121;Nafronyl;Nafronyl Oxalate;Nafronyloxalate;Nafti Puren;Nafti ratiopharm;nafti von ct;Nafti-Puren;Nafti-ratiopharm;Naftidrofuryl;Naftifurin Oxalate;Naftilong;Naftilux;Naftiratiopharm;Oxalate, Nafronyl;Oxalate, Naftifurin;Praxilène;Praxilene

Chemical Property of Nafronyl oxalate

Chemical Property:

• Vapor Pressure: 1.48E-18mmHg at 25°C
• Melting Point: 110-111°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 664.4°C at 760 mmHg
• Flash Point: 355.6°C
• PSA: 113.37000
• Density: 1.2205 (rough estimate)
• LogP: 3.60820
• Solubility.: Freely soluble in water, freely soluble or soluble in ethanol (96 per cent), slightly or sparingly soluble in acetone.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 473.24135246
• Heavy Atom Count: 34
• Complexity: 536

Purity/Quality:

99% ^*data from raw suppliers

Nafronyl oxalate salt analytical standard ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)CCOC(=O)C(CC1CCCO1)CC2=CC=CC3=CC=CC=C32.C(=O)(C(=O)O)O
• Uses: antineoplastic
• Therapeutic Function: Vasodilator
• Clinical Use: Vasodilator: Peripheral and cerebral vascular disease
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Nafronyl oxalate

There total 37 articles about Nafronyl oxalate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

nafronyl (31329-57-4,47583-18-6) + oxalic acid (144-62-7,97993-78-7) → Gevatran (3200-06-4)

Guidance literature:

In water; acetone; for 1h; Reflux;

DOI:10.1021/acs.oprd.5b00361

Reference yield:

oxalic acid (144-62-7,97993-78-7) + (2R,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate (31329-57-4,47583-18-6,86258-34-6,86258-35-7,139240-16-7,139240-17-8,139240-18-9,139240-19-0) → (R)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid (3200-06-4,4825-57-4,29038-64-0,86258-36-8,86258-39-1,139240-24-7,139240-25-8,139240-26-9,139270-29-4)

Guidance literature:

In water; acetone; at 5 ℃; Reflux;

DOI:10.1016/j.bmcl.2012.03.093

Reference yield:

C19H20O5 (1376220-35-7,115025-90-6) → (R)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid (3200-06-4,4825-57-4,29038-64-0,86258-36-8,86258-39-1,139240-24-7,139240-25-8,139240-26-9,139270-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1 h / 130 °C / Neat (no solvent)

2.1: (S)-1-phenyl-ethylamine / diethyl ether / 1 h / 20 °C

2.2: 0 °C / pH 1

3.1: potassium carbonate / water; toluene / 0.5 h / 20 °C

3.2: 90 °C

4.1: water; acetone / 5 °C / Reflux

With (S)-1-phenyl-ethylamine; potassium carbonate; In diethyl ether; water; acetone; toluene;

DOI:10.1016/j.bmcl.2012.03.093

upstream raw materials:

nafronyl

oxalic acid

C₁₉H₂₀O₅

(S)-diethyl 2-[(naphthalen-1-yl)methyl]-3-(tetrahydrofuran-2-yl)malonate

Refernces

• 1、 Hao, Jia,Chen, Bo,Yao, Yiwu,Hossain, Murad,Nagatomo, Takafumi,Yao, Hequan,Kong, Lingyi,Sun, Hongbin. "Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor". . p. 3441 - 3444. Retrieved 2012/06/18.