Oxacyclododec-4-en-2-one, 12-methyl-, (4Z,12S)-

Base Information

• Chemical Name: Oxacyclododec-4-en-2-one, 12-methyl-, (4Z,12S)-
• CAS No.: 86578-99-6
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• Nikkaji Number: J128.598J
• Wikidata: Q76386768
• Metabolomics Workbench ID: 4368
• Mol file: 86578-99-6.mol

Synonyms:S-Cucujolide II;3Z-Dodecen-11S-olide;Oxacyclododec-4-en-2-one, 12-methyl-, (4Z,12S)-;86578-99-6;Ferrulactone II;(s)-dodec-3z-en-11-olide;LMFA07040034

Chemical Property of Oxacyclododec-4-en-2-one, 12-methyl-, (4Z,12S)-

Chemical Property:

• Vapor Pressure: 0.000233mmHg at 25°C
• Boiling Point: 325.3°C at 760 mmHg
• Flash Point: 134.2°C
• PSA: 26.30000
• Density: 0.918g/cm³
• LogP: 3.21860
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 197

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCCCCC=CCC(=O)O1
• Isomeric SMILES: C[C@H]1CCCCCC/C=C\CC(=O)O1

Technology Process of Oxacyclododec-4-en-2-one, 12-methyl-, (4Z,12S)-

There total 48 articles about Oxacyclododec-4-en-2-one, 12-methyl-, (4Z,12S)- 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: 28.0%

(3Z,11S)-11-hydroxy-3-dodecenoic acid (87583-43-5) → ferrulactone II (86578-99-6)

Guidance literature:

With 2,2'-dipyridyldisulphide; silver perchlorate; triphenylphosphine; 1.) THF, 1.5 h, 23 deg C, 2.) xylene, 10 h, reflux;

DOI:10.1021/jo00173a043

Reference yield:

(S)-11-hydroxy-3-dodecynoic acid (87583-41-3) → ferrulactone II (86578-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / P-2 nickel / ethanol / 2 h / Ambient temperature

2: 1.) 2,2'-dipyridyl disulfide, triphenylphosphine; 2.) silver perchlorate / 1.) acetonitrile, 2 h, r.t.; 2.) acetonitrile, xylene, toluene, reflux, 6 h

With 2,2'-dipyridyldisulphide; hydrogen; silver perchlorate; triphenylphosphine; P-2 nickel; In ethanol;

Reference yield:

(S)-11-<(β-methoxyethoxy)-methoxy>-3-dodecyn-1-ol (87519-35-5) → ferrulactone II (86578-99-6)

Guidance literature:

Multi-step reaction with 4 steps

1: CrO₃, 2 N H₂SO₄ / acetone; H₂O / 3 h / 23 °C

2: ZnBr₂ / CH₂Cl₂ / 2 h

3: 1.) sodium borohydride, ethylenediamine, 2.) 5percent HCl / P-2 nickel / 1.) ethanol, 23 deg C, 1 h

4: 28 percent / 2,2'-dipyridyl disulfide, triphenylphosphine, silver perchlorate / 1.) THF, 1.5 h, 23 deg C, 2.) xylene, 10 h, reflux

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; 2,2'-dipyridyldisulphide; sulfuric acid; silver perchlorate; ethylenediamine; triphenylphosphine; zinc dibromide; P-2 nickel; In dichloromethane; water; acetone;

DOI:10.1021/jo00173a043

upstream raw materials:

11-hydroxy-3Z-dodecenoic acid

(3Z,11S)-11-hydroxy-3-dodecenoic acid

methyl 9,10,16-trihydroxyhexadecanoate

methyl ester of azelaic acid aldehyde

Refernces

• 1、 Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.. "Effective synthesis of ferrulactone II based on the use of 2-carboxyethyltriphenylphosphonium bromide". . p. 760 - 763. Retrieved 2007/10/02.
• 2、 Keinan, Ehud,Sinha, Subhash C.,Singh, Surendra P.. "THERMOSTABLE ENZYMES IN ORGANIC SYNTHESIS, 5. TOTAL SYNTHESIS OF S-(+)-Z-DODEC-3-EN-11-OLIDE (FERRULACTONE II) USING A TBADH-GENERATED BIFUNCTIONAL CHIRON.". . p. 4631 - 4638. Retrieved 2007/10/02.