Zerumbone epoxide

Base Information

• Chemical Name: Zerumbone epoxide
• CAS No.: 22471-70-1
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• DSSTox Substance ID: DTXSID001316903
• Mol file: 22471-70-1.mol

Synonyms:Zerumbone oxide;Zerumbone epoxide;UXYYOHOTPOQJPD-MHLOZHTBSA-N;DTXSID001316903;22471-70-1;2,3-Epoxy-6,9-humuladien-8-one

Chemical Property of Zerumbone epoxide

Chemical Property:

• PSA: 29.60000
• LogP: 3.42560
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 390

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCCC2(C(O2)CC(C=CC1=O)(C)C)C
• Isomeric SMILES: C/C/1=C/CCC2(C(O2)CC(/C=C/C1=O)(C)C)C

Technology Process of Zerumbone epoxide

There total 12 articles about Zerumbone epoxide 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: 99.0%

zerumbone (14790-72-8,14790-73-9,14985-60-5,46478-82-4,471-05-6) → (+/-)-(6R,7R)-epoxy-2,6,9,9-tetramethyl-2,10-cycloundecadien-1-one (22471-70-1,74464-32-7,86391-07-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -5 ℃; for 3h;

DOI:10.1271/bbb.65.2193

Reference yield: 97.0%

zerumbone (14790-72-8,14790-73-9,14985-60-5,46478-82-4,471-05-6) → zerumbone epoxide (22471-70-1,74464-32-7,86391-07-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 - 20 ℃; for 25h; regioselective reaction;

DOI:10.1016/j.ejmech.2010.05.029

Reference yield: 94.0%

(2RS,3RS,6RS,7RS)-[10E]-3-(dimethylamino)-6,7-epoxy-2,6,9,9-tetramethylcycloundec-10-en-1-one → zerumbone epoxide (22471-70-1,74464-32-7,86391-07-3)

Guidance literature:

(2RS,3RS,6RS,7RS)-[10E]-3-(dimethylamino)-6,7-epoxy-2,6,9,9-tetramethylcycloundec-10-en-1-one; With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 ℃; for 2h;

With sodium carbonate; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(03)00667-7

upstream raw materials:

(E)-8-Methoxy-3,3,7,11-tetramethyl-12-oxa-bicyclo[9.1.0]dodec-4-en-6-one

zerumbone

sodium methylate

(+/-)-(6R,7R)-epoxy-2,6,9,9-tetramethyl-2,10-cycloundecadien-1-one

Downstream raw materials:

(4Z,7E)-1,5,9,9-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-4,7-dien-6-one