N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide

Base Information

• Chemical Name: N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide
• CAS No.: 177315-87-6
• Molecular Formula: C14H25NO3
• Molecular Weight: 255.35300
• DSSTox Substance ID: DTXSID00436062
• Nikkaji Number: J767.331K
• Wikidata: Q27461120
• Metabolomics Workbench ID: 113004
• ChEMBL ID: CHEMBL8799
• Mol file: 177315-87-6.mol

Synonyms:N-Decanoyl-L-Homoserine lactone;177315-87-6;N-[(3S)-2-oxooxolan-3-yl]decanamide;N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide;CHEMBL8799;C10-HSL;Decanoyl-L-homoserine lactone;Decanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-;c10-Homoserine lactone;HL0;SCHEMBL3140223;DTXSID00436062;CHEBI:190815;BDBM50351509;MFCD11113140;AKOS037646297;AS-67956;HY-136409;CS-0129206;(S)-N-(2-oxotetrahydrofuran-3-yl)decanamide;N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-decanamide;N-Decanoyl-L-homoserine lactone, >=96% (HPLC);J-011268;Q27461120

Chemical Property of N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide

Chemical Property:

• Melting Point: 127-130 °C
• Boiling Point: 466.1±34.0 °C(Predicted)
• PKA: 14.72±0.20(Predicted)
• PSA: 55.40000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 2.94970
• Storage Temp.: ?20°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 255.18344366
• Heavy Atom Count: 18
• Complexity: 266

Purity/Quality:

97% ^*data from raw suppliers

N-Decanoyl-L-homoserine lactone ≥96% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(=O)NC1CCOC1=O
• Isomeric SMILES: CCCCCCCCCC(=O)N[C@H]1CCOC1=O
• Uses: Decanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Burkholderia pseudomallei. Decanoyl-L-homoserine lactone and other acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains.

Technology Process of N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide

There total 12 articles about N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide 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%

(S)-(-)-α-amino-γ-butyrolactone hydrobromide (6305-38-0,15295-77-9,67580-93-2,110045-70-0) + n-decanoyl chloride (112-13-0) → N-(1-oxodecanoyl)-L-homoserine lactone (177315-87-6)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 20 ℃; for 2h; optical yield given as %ee;

DOI:10.1016/j.tetlet.2011.04.059

Reference yield: 80.0%

→ N-(1-oxodecanoyl)-L-homoserine lactone (177315-87-6)

Guidance literature:

Reference yield:

C19H34NO5Pol → N-decanoyl homoserine lactone (18627-37-7,106983-36-2,177315-87-6)

Guidance literature:

With water; trifluoroacetic acid; at 20 ℃; for 48h; Wang resin

DOI:10.1016/j.tetlet.2020.152328

upstream raw materials:

L-homoserine lactone hydrochloride

n-decanoyl chloride

1-decanoic acid

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine