Carbacerulenin

Base Information

• Chemical Name: Carbacerulenin
• CAS No.: 147589-12-6
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• Nikkaji Number: J505.316A
• Mol file: 147589-12-6.mol

Synonyms:carbacerulenin;dl-carbacerulenin

Chemical Property of Carbacerulenin

Chemical Property:

• Vapor Pressure: 9.18E-07mmHg at 25°C
• Boiling Point: 363.8°Cat760mmHg
• Flash Point: 136.7°C
• PSA: 49.83000
• Density: 1.144g/cm³
• LogP: 1.76030
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 332

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CCC=CCCC1(CC(=O)C2C1O2)O
• Isomeric SMILES: C/C=C/C/C=C/CC[C@]1(CC(=O)[C@H]2[C@@H]1O2)O

Technology Process of Carbacerulenin

There total 4 articles about Carbacerulenin 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:

(1R,2S,5R)-((3E,6E)-2-Octa-3,6-dienyl)-6-oxa-bicyclo[3.1.0]hexane-2,4-diol → 2,3-epoxy-4-hydroxy-4-((E,E)-3,6-octadienyl)cyclopentanone (147589-12-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl, -50 to -60 deg C, 20 min;

DOI:10.1248/cpb.40.2954

Reference yield:

(E,E)-3,6-octadienyl iodide (66164-23-6) → 2,3-epoxy-4-hydroxy-4-((E,E)-3,6-octadienyl)cyclopentanone (147589-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tert-butyl lithium / 1.) n-pentane, -78 deg C, 1 h, 2.) n-pentane, THF, -78 deg C, 1.5 h

2: Na, NH₃ / 0.08 h

3: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl, -50 to -60 deg C, 20 min

With oxalyl dichloride; ammonia; tert.-butyl lithium; sodium; dimethyl sulfoxide; triethylamine;

DOI:10.1248/cpb.40.2954

Reference yield:

4-Benzyloxy-6-oxa-bicyclo[3.1.0]hexan-2-one → 2,3-epoxy-4-hydroxy-4-((E,E)-3,6-octadienyl)cyclopentanone (147589-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tert-butyl lithium / 1.) n-pentane, -78 deg C, 1 h, 2.) n-pentane, THF, -78 deg C, 1.5 h

2: Na, NH₃ / 0.08 h

3: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl, -50 to -60 deg C, 20 min

With oxalyl dichloride; ammonia; tert.-butyl lithium; sodium; dimethyl sulfoxide; triethylamine;

DOI:10.1248/cpb.40.2954

upstream raw materials:

(E,E)-3,6-octadienyl iodide

Refernces