1,5-Diphenyl-1,4-pentadiyn-3-one

Base Information

• Chemical Name: 1,5-Diphenyl-1,4-pentadiyn-3-one
• CAS No.: 15814-30-9
• Molecular Formula: C17H10 O
• Molecular Weight: 230.266
• DSSTox Substance ID: DTXSID20166379
• Nikkaji Number: J1.178.330I
• Wikidata: Q83035568
• Mol file: 15814-30-9.mol

Synonyms:1,5-diphenyl-1,4-pentadiyn-3-one

Chemical Property of 1,5-Diphenyl-1,4-pentadiyn-3-one

Chemical Property:

• Vapor Pressure: 7.2E-06mmHg at 25°C
• Boiling Point: 376.5°Cat760mmHg
• Flash Point: 161.4°C
• Density: 1.17g/cm³
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 230.073164938
• Heavy Atom Count: 18
• Complexity: 368

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC(=O)C#CC2=CC=CC=C2

Technology Process of 1,5-Diphenyl-1,4-pentadiyn-3-one

There total 23 articles about 1,5-Diphenyl-1,4-pentadiyn-3-one 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: 95.0%

(S)-5-phenyl-3-(2-phenylethynyl)pent-4-yne-2,3-diol (1431620-35-7) → 1,5-diphenyl-penta-1,4-diyn-3-one (15814-30-9)

Guidance literature:

With SiO₂-supported NaIO₄; In Isopropyl acetate; at 20 ℃; Solvent; Green chemistry;

DOI:10.1039/c8gc03275k

Reference yield: 86.0%

Methyl formate (107-31-3) + phenylacetylene (536-74-3) → 1,5-diphenyl-penta-1,4-diyn-3-one (15814-30-9)

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

Methyl formate; In tetrahydrofuran; at -78 - 23 ℃; for 6h; Inert atmosphere;

With manganese(IV) oxide; In dichloromethane; for 1h;

DOI:10.1021/acs.orglett.7b01222

Reference yield: 83.0%

1,5-diphenylpenta-1,4-diyn-3-ol (15814-32-1) → 1,5-diphenyl-penta-1,4-diyn-3-one (15814-30-9)

Guidance literature:

With barium manganate; In dichloromethane; at 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/jo101125y

upstream raw materials:

1,5-diphenylpenta-1,4-diyn-3-ol

N-ethoxycarbonylaziridine

lithium phenylacetylide

copper(I) phenylacetylenide

Downstream raw materials:

1ξ,5-diphenyl-1ξ-piperidino-pent-1-en-4-yn-3-one

2,6-diphenyl-4H-thiopyran-4-one

1-diethylamino-1,5-diphenyl-pent-1-en-4-yn-3-one

2,6-diphenyl-pyran-4-one

Refernces

Chalcogenopyranones from disodium chalcogenide additions to 1,4- pentadiyn-3-ones. The role of enol ethers as intermediates

10.1002/jhet.5570360322

The research focuses on the synthesis of 4H-chalcogenopyran-4-ones using disodium chalcogenides and enol ethers derived from 1,4-pentadiyn-3-ones. Key chemicals involved include diynones such as 1,5-diphenyl-1,4-pentadiyn-3-one (2a), 1,5-di-tert-butyl-1,4-pentadiyn-3-one (2b), and 1,5-di-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-one (2c), which are reacted with disodium chalcogenides like disodium sulfide, disodium selenide, and disodium telluride. Enol ethers 9 are formed as intermediates from the addition of ethanol to diynones in sodium ethoxide/ethanol, and these enol ethers react with disodium chalcogenides to yield 2,6-disubstituted chalcogenopyranones with high selectivity. The study also examines the addition of hydrogen sulfide to diynones and the role of intermediates in the formation of chalcogenopyranones and dihydrochalcogenophenes. The research aims to improve the synthesis of chalcogenopyranones, which have applications in various fields including as electron-accepting materials in electrophotography and as heat-generating elements in optical recording.