Naftidrofuryl

Base Information

• Chemical Name: Naftidrofuryl
• CAS No.: 31329-57-4
• Deprecated CAS: 860-36-6
• Molecular Formula: C₂₄H₃₃NO₃
• Molecular Weight: 383.531
• Hs Code.: 2932190090
• European Community (EC) Number: 250-572-2
• UNII: 42H8PQ0NMJ
• DSSTox Substance ID: DTXSID3023344
• Nikkaji Number: J20.371H
• Wikipedia: Naftidrofuryl
• Wikidata: Q425867
• NCI Thesaurus Code: C87212
• Metabolomics Workbench ID: 143611
• ChEMBL ID: CHEMBL1620794
• Mol file: 31329-57-4.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 Naftidrofuryl

Chemical Property:

• Vapor Pressure: 7.57E-11mmHg at 25°C
• Melting Point: 80-83°C
• Refractive Index: nD29 1.5513
• Boiling Point: 518.3°Cat760mmHg
• PKA: 9.21±0.25(Predicted)
• Flash Point: 267.3°C
• PSA: 38.77000
• Density: 1.079g/cm³
• LogP: 4.45260
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 383.24604391
• Heavy Atom Count: 28
• Complexity: 465

Purity/Quality:

99.9% ^*data from raw suppliers

Nafronyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCOC(=O)C(CC1CCCO1)CC2=CC=CC3=CC=CC=C32
• Uses: Nafronyl is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication. Vasodilator. Nafronyl is a selective inhibitor of serotonin receptors
• Therapeutic Function: Vasodilator

Technology Process of Naftidrofuryl

There total 64 articles about Naftidrofuryl 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: 98.0%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + (2R,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4,115025-92-8,115025-93-9,139240-21-4,139240-22-5,139240-23-6,139240-20-3) → (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)

Guidance literature:

2-chloro-N,N-diethylethylamine hydrochloride; (2R,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique; With potassium carbonate; In water; toluene; at 20 ℃; for 0.5h;

With benzyltrimethylammonium chloride; In water; toluene; at 90 ℃;

DOI:10.1016/j.bmcl.2012.03.093

Reference yield:

furfural (98-01-1) → nafronyl (31329-57-4,47583-18-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / piperidine, acetic acid / toluene / 1.) 100-104 deg C, 1.5 h, 2.) 110-120 deg C, 4 h.

2: 88 percent / hydrogen / Raney Ni / ethanol / 6 h / 80 °C / 56254.5 Torr

3: 76 percent / sodium ethoxide / ethanol

4: 60 percent / 85percent KOH / H₂O; ethanol / 3 h / Heating

With piperidine; potassium hydroxide; hydrogen; sodium ethanolate; acetic acid; nickel; In ethanol; water; toluene;

Reference yield:

ethyl 2-carbethoxy-3-(2-furanyl)propenoate (17448-96-3) → nafronyl (31329-57-4,47583-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / hydrogen / Raney Ni / ethanol / 6 h / 80 °C / 56254.5 Torr

2: 76 percent / sodium ethoxide / ethanol

3: 60 percent / 85percent KOH / H₂O; ethanol / 3 h / Heating

With potassium hydroxide; hydrogen; sodium ethanolate; nickel; In ethanol; water;

upstream raw materials:

1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid

dimethyl sulfate

2-(Diethylamino)ethanol

tetrahydrofurfuryl bromide

Downstream raw materials:

Gevatran

(R)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid

(R)-3-Naphthalen-1-yl-2-[(R)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid

(S)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid

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.
• 2、 Valenta, Vladimir,Holubek, Jiri,Svatek, Emil,Miller, Vladimir,Vlkova, Marie,Protiva, Miroslav. "2-DIETHYLAMINOETHYL ESTERS OF 1,3-DISUBSTITUTED PROPANE-2-CARBOXYLIC ACIDS". . p. 2534 - 2544. Retrieved 2007/10/02.