2-[(5Z)-tetradec-5-en-1-yl]cyclobutan-1-one

Base Information

• Chemical Name: 2-[(5Z)-tetradec-5-en-1-yl]cyclobutan-1-one
• CAS No.: 173074-85-6
• Molecular Formula: C18H32O
• Molecular Weight: 264.45
• DSSTox Substance ID: DTXSID801291668
• Nikkaji Number: J705.795D
• Metabolomics Workbench ID: 47813
• Mol file: 173074-85-6.mol

Synonyms:2-[(Z)-tetradec-5-enyl]cyclobutan-1-one;2-[(5Z)-tetradec-5-en-1-yl]cyclobutan-1-one;173074-85-6;(Z)-2-(Tetradec-5-en-1-yl)cyclobutan-1-one;starbld0001676;CHEBI:172506;DTXSID801291668;(Z)-2-(5-Tetradecenyl)cyclobutanone;2-[(Z)-5-Tetradecenyl]cyclobutanone;2-[(5Z)-5-tetradecenyl]cyclobutanone;(+-)-(Z)-2-(5-Tetradecenyl)cyclobutanone;2-[(5z)-5-tetradecen-1-yl] cyclobutanone;(+/-)-(Z)-2-(5-Tetradecenyl)cyclobutanone

Chemical Property of 2-[(5Z)-tetradec-5-en-1-yl]cyclobutan-1-one

Chemical Property:

• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 264.245315640
• Heavy Atom Count: 19
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

2-(5Z)-5-Tetradecen-1-yl-cyclobutanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCC1CCC1=O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCC1CCC1=O
• Uses: 2-(5Z)-5-Tetradecen-1-yl-cyclobutanone is used as a marker for the detection of irradiated mango, papaya, Camembert cheese and salmon meat.

Technology Process of 2-[(5Z)-tetradec-5-en-1-yl]cyclobutan-1-one

There total 12 articles about 2-[(5Z)-tetradec-5-en-1-yl]cyclobutan-1-one 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%

(Z)-1-(1-Ethoxy-cyclopropyl)-pentadec-6-en-1-ol → 2-(tetradec-5-enyl)cyclobutanone (173074-85-6)

Guidance literature:

With tetrafluoroboric acid; In diethyl ether; for 96h; Ambient temperature;

DOI:10.1039/P19960000139

Reference yield: 60.0%

(E)-1-(1-Ethoxy-cyclopropyl)-pentadec-6-en-1-ol → trans-2-(tetradec-5'-enyl)cyclobutanone (173074-85-6)

Guidance literature:

With tetrafluoroboric acid; In diethyl ether; for 96h; Ambient temperature;

DOI:10.1039/P19960000139

Reference yield:

(R)-1-Amino-2-(methoxymethyl)pyrrolidine (72748-99-3,187035-29-6) → (R)-(-)-2-(tetradec-5-enyl)-cyclobutanone (173074-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; titanium(IV) chloride / diethyl ether / Heating

2.1: LDA / tetrahydrofuran / 4 h / -78 °C

2.2: tetrahydrofuran / 20 h / -78 - -50 °C

2.3: oxalic acid / H₂O; diethyl ether; tetrahydrofuran / -78 - 20 °C

With titanium tetrachloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tetasy.2005.04.012

upstream raw materials:

1-Iodooctane

5-hexyl-1-ol

(Z)-tetradec-5-en-1-ol

tetradec-5-ynol