3-(Naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoic acid

Base Information

• Chemical Name: 3-(Naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoic acid
• CAS No.: 25379-26-4
• Molecular Formula: C18H20 O3
• Molecular Weight: 284.355
• Hs Code.: 2932190090
• European Community (EC) Number: 246-926-0
• DSSTox Substance ID: DTXSID20948218
• Nikkaji Number: J109.281B
• Mol file: 25379-26-4.mol

Synonyms:naphthidrofurylic acid

Chemical Property of 3-(Naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoic acid

Chemical Property:

• Vapor Pressure: 2.04E-09mmHg at 25°C
• Boiling Point: 464.2°C at 760 mmHg
• PKA: 4.44±0.11(Predicted)
• Flash Point: 169.1°C
• PSA: 46.53000
• Density: 1.183g/cm³
• LogP: 3.65220
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 284.14124450
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

99.9% ^*data from raw suppliers

Tetrahydro-α-(1-naphthalenylmethyl)-2-furanpropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1)CC(CC2=CC=CC3=CC=CC=C32)C(=O)O
• Uses: Tetrahydro-α-(1-naphthalenylmethyl)-2-furanpropanoic Acid is a Nafronyl (N215000) derivative. Nafronyl is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.

Technology Process of 3-(Naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoic acid

There total 54 articles about 3-(Naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoic acid 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: 96.0%

1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid (113527-39-2,115025-90-6) → acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4)

Guidance literature:

1.) 140 deg C, 1 h, 2.) 160 deg C, 1 h.;

Reference yield: 23.0%

2-[(naphthalen-1-yl)methyl]-3-[(S)-tetrahydrofuran-2-yl]propanoic acid (1392400-74-6) → (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)

Guidance literature:

2-[(naphthalen-1-yl)methyl]-3-[(S)-tetrahydrofuran-2-yl]propanoic acid; With (S)-1-phenyl-ethylamine; In diethyl ether; at 20 ℃; for 1h;

With hydrogenchloride; In water; at 0 ℃; pH=1; Further stages;

DOI:10.1016/j.bmcl.2012.03.093

Reference yield:

furfural (98-01-1) → acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4)

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

5: 96 percent / 1.) 140 deg C, 1 h, 2.) 160 deg C, 1 h.

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

upstream raw materials:

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

tetrahydrofurfuryl bromide

Tetrahydrofurfuryl alcohol

furfural

Downstream raw materials:

(2R,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate

(2R,2'R)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate

(2S,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate

(2S,2'R)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate

Refernces

• 1、 Descours,Festal,Leger,Carpy. "Optical isomers of naftidrofuryl (=2-(diethylamino)ethyl 2-[(naphth-1-yl)methyl]-3-(tetrahydrofur-2-yl)propanoate)". . p. 1757 - 1763. Retrieved 2007/10/02.