Megastigmatrienone A

Base Information

• Chemical Name: Megastigmatrienone A
• CAS No.: 5492-79-5
• Molecular Formula: C13H18O
• Molecular Weight: 190.285
• European Community (EC) Number: 236-187-2,226-825-8,225-943-7
• UNII: 3QY2F7PCN3
• DSSTox Substance ID: DTXSID501315386
• Nikkaji Number: J399.359K,J210.556J,J213.756I
• Wikidata: Q22137252
• Metabolomics Workbench ID: 158060
• Mol file: 5492-79-5.mol

Synonyms:(4Z)-4-((E)-but-2-enylidene)-3,5,5-trimethylcyclohex- 2-en-1-one;megastigmatrienone

Chemical Property of Megastigmatrienone A

Chemical Property:

• PSA: 17.07000
• LogP: 3.43420
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 190.135765193
• Heavy Atom Count: 14
• Complexity: 327

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=C1C(=CC(=O)CC1(C)C)C
• Isomeric SMILES: C/C=C/C=C/1\C(=CC(=O)CC1(C)C)C

Technology Process of Megastigmatrienone A

There total 6 articles about Megastigmatrienone A 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:

Methanesulfonic acid (E)-1-(2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-but-2-enyl ester → (E)-4-<(Z)-But-2-enylidene>-3,5,5-trimethylcyclohex-2-enone (5298-13-5) + (E)-4-<(E)-But-2-enylidene>-3,5,5-trimethylcyclohex-2-enone (5164-78-3) + (Z)-4-<(Z)-But-2-enylidene>-3,5,5-trimethylcyclohex-2-enone (5164-79-4) + (Z)-4-<(E)-But-2-enylidene>-3,5,5-trimethylcyclohex-2-enone (5492-79-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In toluene; for 1h; Yield given. Yields of byproduct given; Heating;

DOI:10.1246/bcsj.55.1907

Reference yield:

7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one (14203-64-6) → (Z)-4-<(E)-But-2-enylidene>-3,5,5-trimethylcyclohex-2-enone (5492-79-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Li / tetrahydrofuran / 1.) 10-15 deg C, 2.) r.t., 1 h

2: 80 percent / PBr₃, pyridine / toluene / 1 h / -10 °C

With pyridine; phosphorus tribromide; lithium; In tetrahydrofuran; toluene;

Reference yield:

8-(But-3-enyl)-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol (149457-31-8) → (Z)-4-<(E)-But-2-enylidene>-3,5,5-trimethylcyclohex-2-enone (5492-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / PBr₃, pyridine / toluene / 1 h / -10 °C

With pyridine; phosphorus tribromide; In toluene;

upstream raw materials:

6-Bromo-8-but-3-enyl-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-7-ene

7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one

8-(But-3-enyl)-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol