Macamide 1

Base Information

• Chemical Name: Macamide 1
• CAS No.: 74058-71-2
• Molecular Formula: C23H39NO
• Molecular Weight: 345.569
• UNII: 1M5UVS8JUU
• DSSTox Substance ID: DTXSID50458532
• Nikkaji Number: J603.433K
• Wikidata: Q27252600
• Pharos Ligand ID: CVX4M75MW6R5
• ChEMBL ID: CHEMBL2415102
• Mol file: 74058-71-2.mol

Synonyms:N-benzylhexadecanamide

Chemical Property of Macamide 1

Chemical Property:

• Melting Point: 95-96℃
• Boiling Point: 501.9±29.0 °C(Predicted)
• PKA: 16.39±0.46(Predicted)
• PSA: 32.59000
• Density: 0.919±0.06 g/cm3(Predicted)
• LogP: 7.62440
• Storage Temp.: 2-8°C
• Solubility.: ≤2mg/ml in organic solvent ethanol
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 16
• Exact Mass: 345.303164868
• Heavy Atom Count: 25
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

Macamide B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C1
• Uses: N-Benzyl Hexadecanamide is a non-?polar, long-?chain fatty acid N-?benzylamide part of a group of macamides tested as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH)?.

Technology Process of Macamide 1

There total 12 articles about Macamide 1 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: 100.0%

C28H40N2O2 (100663-86-3) + benzylamine (100-46-9) → hexadecanoic acid benzylamide (74058-71-2) + (E)-2-pyridylphenyl ketoxime (14178-31-5)

Guidance literature:

In dichloromethane; for 24h; Ambient temperature;

DOI:10.1246/cl.1985.701

Reference yield: 96.0%

1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one (74058-64-3) + benzylamine (100-46-9) → hexadecanoic acid benzylamide (74058-71-2)

Guidance literature:

In dichloromethane; for 0.0333333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)71520-6

Reference yield: 94.0%

glyceroltripalmitate (555-44-2) + benzylamine (100-46-9) → hexadecanoic acid benzylamide (74058-71-2)

Guidance literature:

at 50 - 60 ℃; for 16h;

DOI:10.1007/BF02540463

upstream raw materials:

1-hexadecylcarboxylic acid

benzylamine

hexadecanoic acid ethyl ester

n-hexadecanoyl chloride

Refernces

• 1、 Neumann, Karoline T.,Donslund, Aske S.,Andersen, Thomas L.,Nielsen, Dennis U.,Skrydstrup, Troels. "Synthesis of Aliphatic Carboxamides Mediated by Nickel NN2-Pincer Complexes and Adaptation to Carbon-Isotope Labeling". . p. 14946 - 14949. Retrieved 2018/09/25.
• 2、 Al-Azani, Mariam,al-Sulaibi, Mazen,al Soom, Nuha,Al Jasem, Yosef,Bugenhagen, Bernhard,Al Hindawi, Bassam,Thiemann, Thies. "The use of BrCCl3-PPh3 in Appel type transformations to esters, O-acyloximes, amides, and acid anhydrides". . p. 921 - 932. Retrieved 2016/08/08.