Pummerer's ketone

Base Information

• Chemical Name: Pummerer's ketone
• CAS No.: 546-24-7
• Molecular Formula: C14H14O2
• Molecular Weight: 214.264
• Hs Code.: 2932999099
• NSC Number: 169999
• DSSTox Substance ID: DTXSID90969854
• Nikkaji Number: J105.218G
• Mol file: 546-24-7.mol

Synonyms:Pummerer's ketone;546-24-7;8,9b-Dimethyl-4a,9b-dihydrodibenzo[b,d]furan-3(4H)-one;Pummerer//'s ketone;8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-one;3(4H)-Dibenzofuranone, 4a,9b-dihydro-8,9b-dimethyl-;NSC169999;NSC 169999;SCHEMBL11881321;DTXSID90969854;RGTPQXAKJODXMX-UHFFFAOYSA-N;AKOS000280155;AKOS040765197;NSC-169999;3(4H)-Dibenzofuranone,9b-dihydro-8,9b-dimethyl-;AA-516/30011016;4a,9b-dihydro-8,9b-dimethyl-3(4h)-dibenzofuranone;8,9b-Dimethyl-4a,9b-dihydrodibenzo[b,d]furan-3(4H)-one #

Chemical Property of Pummerer's ketone

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.584
• Boiling Point: 296.9 °C at 760 mmHg
• Flash Point: 123.4 °C
• PSA: 26.30000
• Density: 1.174 g/cm³
• LogP: 2.54270
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 214.099379685
• Heavy Atom Count: 16
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

4ALPHA,9BETA-DIHYDRO-8,9BETA-DIMETHYL-3(4H)-DIBENZOFURANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)OC3C2(C=CC(=O)C3)C

Technology Process of Pummerer's ketone

There total 12 articles about Pummerer's ketone 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: 68.0%

p-cresol (106-44-5) → Pummerer ketone (546-24-7) + 4-fluoro-4-methylcyclohexa-2,5-dien-1-one (77249-33-3)

Guidance literature:

With pyridinium polyhydrogen fluoride; bis-[(trifluoroacetoxy)iodo]benzene; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)77165-6

Reference yield: 42.0%

1-((4aS,9bS)-8,9b-Dimethyl-4a,9b-dihydro-dibenzofuran-3-yl)-pyrrolidine (31704-63-9,121942-34-5) + Nitrosobenzene (586-96-9) → 4a,9b-dihydro-8,9b-dimethyl-3-(4H)-dibenzofuranone (Pummerer's ketone) (546-24-7,15413-34-0,68789-13-9) + 4-Anilino-1,2,4aβ,9b-tetrahydro-8,9bβ-dimethyl-1β,4β-(N-phenylepimino)dibenzofuran-3(4H)-one (135347-85-2) + C28H24O6

Guidance literature:

In tetrachloromethane; at -5 ℃; equimolecular;

Reference yield: 29.0%

p-cresol (106-44-5) → 4a,9b-dihydro-8,9b-dimethyl-3-(4H)-dibenzofuranone (Pummerer's ketone) (546-24-7,15413-34-0,68789-13-9) + 4-hydroxy-4-methyl-cyclohexa-2,5-dienone (23438-23-5)

Guidance literature:

With oxygen; rose bengal; In acetone; at 0 ℃; for 10h; Irradiation; var. solv.;

DOI:10.1016/S0040-4020(01)89229-2

upstream raw materials:

p-cresol

1-((4aS,9bS)-8,9b-Dimethyl-4a,9b-dihydro-dibenzofuran-3-yl)-pyrrolidine

Nitrosobenzene

benzophenone

Downstream raw materials:

2-[4-Methyl-2-(1-methyl-4-oxo-cyclohexa-2,5-dienyl)-phenoxy]-acetamide

(4aS,9bR)-4-[1-Dimethylamino-meth-(E)-ylidene]-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one

(1S,4aR,9bR)-8,9b-Dimethyl-1-phenyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one

(+/-)-8,9b-dimethyl-(4ar,9bc)-4a,9b-dihydro-4H-dibenzofuran-3-one-(2,4-dinitro-phenylhydrazone)

Refernces

SOME CHEMICAL TRANSFORMATIONS OF PUMMERER'S KETONE

10.1016/S0040-4020(01)92063-0

The research aimed to explore chemical transformations of Pummerer's Ketone to synthesize molecules with simplified morphine structures, potentially leading to the development of analgesics with improved properties. The study focused on converting Pummerer's Ketone into compounds with nitrogen-bearing functions at the C-4 position, thereby approximating the morphine skeleton. The study concluded that certain conditions, such as the use of cerous chloride with NaBH4, could influence the selectivity of the reduction process. Additionally, the addition of N,N-diethylaminopropyne provided a successful route to introduce a nitrogen atom into the molecule, leading to the formation of an amide.