2-Methyl-5-(1,2,2-trimethyl-4-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione

Base Information

• Chemical Name: 2-Methyl-5-(1,2,2-trimethyl-4-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione
• CAS No.: 306951-08-6
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 306951-08-6.mol

Synonyms:2-methyl-5-(1,2,2-trimethyl-4-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione

Chemical Property of 2-Methyl-5-(1,2,2-trimethyl-4-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C(=CC1=O)C2(CC(=O)CC2(C)C)C

Technology Process of 2-Methyl-5-(1,2,2-trimethyl-4-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione

There total 6 articles about 2-Methyl-5-(1,2,2-trimethyl-4-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione 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: 94.0%

(R)-3-(2,5-dimethoxy-4-methylphenyl)-2,2,3-trimethylcyclopentanone (733002-21-6) → (S)-2-methyl-5-(1,2,2-trimethyl-3-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione (306951-08-6)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.833333h; Inert atmosphere;

DOI:10.1021/jacs.1c07966

Reference yield:

(R)-4-(2,5-dimethoxy-4-methylphenyl)-4,5,5-trimethylcyclopent-2-en-1-one (733001-86-0) → (S)-2-methyl-5-(1,2,2-trimethyl-3-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione (306951-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 mg / hydrogen / Pd-C / ethyl acetate / 16 h / 20 °C

2: 71 mg / ceric ammonium nitrate / acetonitrile; H₂O / 0.5 h / 0 °C

With ammonium cerium(IV) nitrate; hydrogen; palladium on activated charcoal; In water; ethyl acetate; acetonitrile;

DOI:10.1271/bbb.69.374

Reference yield:

C15H20O2 → (S)-2-methyl-5-(1,2,2-trimethyl-3-oxocyclopentyl)cyclohexa-2,5-diene-1,4-dione (306951-08-6)

Guidance literature:

With potassium nitrososulfonate; In aq. phosphate buffer; water; acetone; at 20 ℃; for 12h; pH=7;

DOI:10.1002/chem.201203395

upstream raw materials:

(2R,5R)-5,8,10,10-tetramethyl-2,3,4,5-tetrahydro-2,5-methanobenzo[b]oxepine-2,7-diol

(R)-3-(2,5-dimethoxy-4-methylphenyl)-2,2,3-trimethylcyclopentanone

(R)-4-(2,5-dimethoxy-4-methylphenyl)-4,5,5-trimethylcyclopent-2-en-1-one

Refernces

The First Total Synthesis of the Antimicrobial Sesquiterpenes (±)-Enokipodins A and B

10.1055/s-2003-45003

The study reports the first total synthesis of antimicrobial sesquiterpenes (±)-enokipodins A and B, along with the formal total synthesis of cuparene-1,4-diol and cuparene-1,4-quinone. The synthesis starts from 2,5-dimethoxy-4-methylacetophenone, using Claisen rearrangement and ring-closing metathesis as key steps. Enokipodins A and B exhibit significant antimicrobial activity against certain fungi and bacteria. The study aims to develop a methodology for synthesizing these compounds due to their interesting biological properties.