Oxacycloheptadecan-2-one

Base Information

• Chemical Name: Oxacycloheptadecan-2-one
• CAS No.: 109-29-5
• Molecular Formula: C16H30 O2
• Molecular Weight: 254.413
• Hs Code.: 2932209090
• European Community (EC) Number: 203-662-0
• NSC Number: 33546
• UNII: 64E2HO00C7
• DSSTox Substance ID: DTXSID4047622
• Nikkaji Number: J65.679H
• Wikidata: Q21099108
• Metabolomics Workbench ID: 4388
• ChEMBL ID: CHEMBL3189021
• Mol file: 109-29-5.mol

Synonyms:hexadecanolide

Chemical Property of Oxacycloheptadecan-2-one

Chemical Property:

• Appearance/Colour: colourless to light yellow solid
• Vapor Pressure: 2.6E-05mmHg at 25°C
• Melting Point: 34-38 °C(lit.)
• Refractive Index: n20/D1.4680-1.4730
• Boiling Point: 188 °C / 15mmHg
• Flash Point: 149.6°C
• PSA: 26.30000
• Density: 0.879g/cm³
• LogP: 5.00460
• Storage Temp.: −20°C
• Water Solubility.: Insoluble in water.
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 201

Purity/Quality:

99.9% ^*data from raw suppliers

16-Hexadecanolide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCCCCCCC(=O)OCCCCCCC1
• Uses: 16-Hexadecanolide is used in the manfacturing of perfumes. It acts as masking agents. 16-Hexadecanolide may be used as a starting reagent in the synthesis of caeliferin A 16:0.

Technology Process of Oxacycloheptadecan-2-one

There total 39 articles about Oxacycloheptadecan-2-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: 98.0%

(10E/Z)-oxacycloheptadec-10-en-2-one (28645-51-4) → 15-hexadecanolide (109-29-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In diethyl ether; under 760 Torr;

DOI:10.1055/s-1987-27867

Reference yield: 97.0%

16-hydroxyhexadecanoic acid (506-13-8) → 15-hexadecanolide (109-29-5)

Guidance literature:

With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; chloroform; for 18h; Reflux; Inert atmosphere;

DOI:10.1039/c0ob00161a

Reference yield: 93.0%

(Z)-Oxacycloheptadec-15-en-2-one → 15-hexadecanolide (109-29-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; Ambient temperature;

DOI:10.1039/c39810001123

upstream raw materials:

16-bromohexadecanoic acid

16-hydroxyhexadecanoic acid

cyclohexadecanone

16-iodohexadecanoic acid

Downstream raw materials:

Ethyl myristate

1-hexadecanol-15-one

1,16-hexadecanediol

16-bromohexadecanoic acid

Refernces

• 1、 Hunsdiecker. "-". . . Retrieved 1944.
• 2、 Kuno, Hideyuki,Shibagaki, Makoto,Takahashi, Kyoko,Honda, Ichiro,Matsushita, Hajime. "Lactonization of ω-Hydroxy Esters over Hydrous Zirconium(IV) Oxide". . p. 571 - 574. Retrieved 1992.
• 3、 Rico,Halvorsen,Dubrule,Lattes. "Effect of micelles on cyclization reactions: The use of N-hexadecyl-2- chloropyridinium iodide as an amphiphilic carboxyl-activating agent in lactonization and lactamization". . p. 415 - 420. Retrieved 1994.
• 4、 Ciofini, Ilaria,Force, Guillaume,Leb?uf, David,Mayer, Robert J.,Perfetto, Anna. "Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**". supporting information. p. 19843 - 19851. Retrieved 2021/08/13.
• 5、 Dumas, Adrien,Colombel-Rouen, Sophie,Curbet, Idriss,Forcher, Gwénael,Tripoteau, Fabien,Caijo, Frédéric,Queval, Pierre,Rouen, Mathieu,Baslé, Olivier,Mauduit, Marc. "Highly selective macrocyclic ring-closing metathesis of terminal olefins in non-chlorinated solvents at low dilution". . p. 436 - 443. Retrieved 2019/01/28.