Cyclohexyl biphenyl-3-ylcarbamate

Base Information

• Chemical Name: Cyclohexyl biphenyl-3-ylcarbamate
• CAS No.: 565460-15-3
• Molecular Formula: C₁₉H₂₁NO₂
• Molecular Weight: 295.381
• Hs Code.: 2924299090
• UNII: B8371SFA9K
• DSSTox Substance ID: DTXSID90450611
• Nikkaji Number: J2.229.172F
• Wikipedia: URB602
• Wikidata: Q7865593
• ChEMBL ID: CHEMBL77767
• Mol file: 565460-15-3.mol

Synonyms:URB602

Chemical Property of Cyclohexyl biphenyl-3-ylcarbamate

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122-123 °C
• Refractive Index: 1.595
• Boiling Point: 416.611 °C at 760 mmHg
• Flash Point: 205.759 °C
• PSA: 38.33000
• Density: 1.149 g/cm³
• LogP: 5.30780
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 295.157228913
• Heavy Atom Count: 22
• Complexity: 345

Purity/Quality:

99.0% ^*data from raw suppliers

URB602 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)OC(=O)NC2=CC=CC(=C2)C3=CC=CC=C3
• Uses: URB602 is a selective inhibitor of MGL, exhibiting an IC50 of 28 for the rat brain enzyme. It does not inhibit fatty acid amide hydrolase (FAAH) at concentrations up to 100 , or other lipid metabolizing enzymes such as diacylglycerol lipase or URB602 is a selective inhibitor of MGL, exhibiting an IC50 of 28 μM for the rat brain enzyme. It does not inhibit fatty acid amide hydrolase (FAAH) at concentrations up to 100 μM, or other lipid metabolizing enzymes such as diacylglycerol lipase or cyclooxygenase-2.5 6 Inhibition of 2-AG hydrolysis is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.

Technology Process of Cyclohexyl biphenyl-3-ylcarbamate

There total 6 articles about Cyclohexyl biphenyl-3-ylcarbamate 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: 75.0%

potassium cyanate (590-28-3) + 3-bromobiphenyl (2113-57-7) + cyclohexanol (108-93-0) → biphenyl-3-yl-carbamic acid cyclohexyl ester (565460-15-3)

Guidance literature:

With potassium phosphate; copper(l) iodide; 2-((2-methylnaphthalen-1-yl)amino)-2-oxoacetic acid; at 110 ℃; for 36h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.7b03175

Reference yield:

cyclohexanol (108-93-0) + imidazole-1-carboxylic acid biphenyl-3-ylamide → biphenyl-3-yl-carbamic acid cyclohexyl ester (565460-15-3)

Guidance literature:

In acetonitrile; for 24h; Heating;

DOI:10.1021/jm021119g

Reference yield:

3-biphenyl amine (2243-47-2) → biphenyl-3-yl-carbamic acid cyclohexyl ester (565460-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP / acetonitrile / 14 h / Heating

2: 86 mg / acetonitrile / 24 h / Heating

With dmap; In acetonitrile;

DOI:10.1021/jm021119g

upstream raw materials:

cyclohexanol

3-biphenyl amine

m-Bromoaniline

phenylboronic acid

Refernces

• 1、 Kumar, S. Vijay,Ma, Dawei. "Synthesis of N-(Hetero)aryl Carbamates via CuI/MNAO Catalyzed Cross-Coupling of (Hetero)aryl Halides with Potassium Cyanate in Alcohols". . p. 2706 - 2713. Retrieved 2018/03/09.
• 2、 Tarzia, Giorgio,Duranti, Andrea,Tontini, Andrea,Piersanti, Giovanni,Mor, Marco,Rivara, Silvia,Plazzi, Pier Vincenzo,Park, Chris,Kathuria, Satish,Piomelli, Daniele. "Design, synthesis, and structure - Activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors". . p. 2352 - 2360. Retrieved 2007/10/03.