Anacyclin

Base Information

• Chemical Name: Anacyclin
• CAS No.: 502-57-8
• Molecular Formula: C₁₈H₂₅NO
• Molecular Weight: 271.403
• DSSTox Substance ID: DTXSID701184838
• Metabolomics Workbench ID: 70147
• Nikkaji Number: J358.117I
• Wikidata: Q27105770
• Mol file: 502-57-8.mol

Synonyms:Anacyclin;AC1NQY2W;C08396;(2E,4E)-N-(2-Methylpropyl)-2,4-tetradecadiene-8,10-diynamide;(2E,4E)-N-(2-methylpropyl)tetradeca-2,4-dien-8,10-diynamide;(2E,4E)-N-isobutyltetradeca-2,4-dien-8,10-diynamide;502-57-8;CHEBI:2698;DTXSID701184838;LMFA08020165;94413-18-0;Q27105770

Chemical Property of Anacyclin

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 271.193614421
• Heavy Atom Count: 20
• Complexity: 457

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC#CC#CCCC=CC=CC(=O)NCC(C)C
• Isomeric SMILES: CCCC#CC#CCC/C=C/C=C/C(=O)NCC(C)C

Technology Process of Anacyclin

There total 14 articles about Anacyclin 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: 65.0%

pentynyl bromide (14752-60-4) + N-isobutyl-nona-2t,4t-dien-8-ynamide (18679-26-0) → anacycline (502-57-8,94413-18-0)

Guidance literature:

DOI:10.1016/S0040-4039(00)96649-8

Reference yield:

hexa-1,5-diyn-1-yltrimethylsilane (1578-34-3) → anacycline (502-57-8,94413-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Cp₂ZrCl(H) / 2.) (Ph₃P)2Pd(O) / 1.) RT, benzene, 2.) solvent: THF-C₆H₆

2: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: 65 percent

With Schwartz's reagent; tetrabutyl ammonium fluoride; bis(triphenylphosphine)palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96649-8

Reference yield:

(E)-N-(2-methylpropyl)-3-bromoacrylamide (110922-33-3) → anacycline (502-57-8,94413-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaI, AlCl₃ / acetone

2: 1.) Cp₂ZrCl(H) / 2.) (Ph₃P)2Pd(O) / 1.) RT, benzene, 2.) solvent: THF-C₆H₆

3: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran

4: 65 percent

With Schwartz's reagent; aluminium trichloride; tetrabutyl ammonium fluoride; sodium iodide; bis(triphenylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4039(00)96649-8

upstream raw materials:

1-Pentyne

N-isobutyl-nona-2t,4t-dien-8-ynamide

tetradeca-2t,4t-diene-8,10-diynoic acid

(E)-(4-(isobutylamino)-4-oxobut-2-enyl)triphenylphosphonium bromide

Refernces