3-Hexene-2,5-dione, 3,4-diacetyl-

Base Information

• Chemical Name: 3-Hexene-2,5-dione, 3,4-diacetyl-
• CAS No.: 27871-55-2
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 2914190090
• DSSTox Substance ID: DTXSID30473107
• Nikkaji Number: J88.524J
• Wikidata: Q82302277
• Mol file: 27871-55-2.mol

Synonyms:3-Hexene-2,5-dione, 3,4-diacetyl-;27871-55-2;tetraacetylethylene;SCHEMBL660480;DTXSID30473107

Chemical Property of 3-Hexene-2,5-dione, 3,4-diacetyl-

Chemical Property:

• PSA: 68.28000
• LogP: 0.63900
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 281

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=C(C(=O)C)C(=O)C)C(=O)C

Technology Process of 3-Hexene-2,5-dione, 3,4-diacetyl-

There total 5 articles about 3-Hexene-2,5-dione, 3,4-diacetyl- 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: 84.0%

acetylacetone (123-54-6,81235-32-7) → 3,4-diacetylhex-3-ene-2,5-dione (27871-55-2)

Guidance literature:

With nitric acid; cerous nitrate; In acetonitrile; at 25 ℃; for 23h; electrolysis, 1.4 V vs SCE;

DOI:10.1016/0040-4039(95)01921-4

Reference yield: 69.0%

tetraacetyleneethane → 3,4-diacetylhex-3-ene-2,5-dione (27871-55-2)

Guidance literature:

With barium manganate; acetic acid; In dichloromethane; for 6h; Heating; ultrasonic irradiation;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3343::AID-EJOC3343>3.0.CO;2-S

Reference yield:

3,4-diacetyl-hex-3-ene-2,5-dione; bis-thallium(1+) 1,2;5,6-bis-enolate → 3,4-diacetylhex-3-ene-2,5-dione (27871-55-2)

Guidance literature:

With iodine; In diethyl ether;

DOI:10.1039/j39700001536

upstream raw materials:

1,1,2,2-Tetraacetylethan

acetylacetone

Downstream raw materials:

1,1,2,2-Tetraacetylethan

4,4,5,5-tetraacetyl-1,2-dimethylcyclohex-1-ene

9-acetyl-1,2-di(p-toluoyl)-6,8-dimethyl-6-hydroxy-4-oxa-1,2-diaza spiro<4.4>non-8-ene

2,6-Dichloro-benzaldehyde O-(3,4-diacetyl-5-hydroxy-2,5-dimethyl-2,5-dihydro-furan-2-yl)-oxime

Refernces

Tetraacylethenes as dienophiles and hetero dienes in two-step Diels- Alder reactions

10.1002/(SICI)1099-0690(199912)1999:12<3343::AID-EJOC3343>3.0.CO;2-S

The research explores the synthesis and reactivity of tetraacylethenes, specifically tetraacetylethylene (7a) and diacetyldibenzoylethylene (7b), in Diels–Alder reactions. The study aims to provide a novel access to functionalized [4.3.3]propellanes and clarify conflicting reports on the oxidative coupling of benzoylacetone (15b). The researchers found that tetraacetylethylene (7a) behaves as a mechanistic chameleon, yielding two different Diels–Alder products with 1,2-dimethylenecyclohexane, and can react as both an electron-deficient dienophile and a 1-oxa-1,3-diene. Key chemicals used in the process include barium manganate, iodosobenzene, 1,2-dimethylenecyclohexane, and various derivatives of benzoylacetone. The conclusions drawn from the study are that tetraacetylethylene (7a) is a versatile reactant in Diels–Alder reactions, capable of forming different products depending on the reaction conditions, and that the reactions likely proceed via a zwitterionic intermediate, offering insights into the ambiguity observed in the Diels–Alder chemistry of such compounds.

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