141726-24-1

Basic information

• Product Name: 1-PHENYLNON-7-YNE-1,3-DIONE
• Synonyms: 1-PHENYLNON-7-YNE-1,3-DIONE
• CAS NO: 141726-24-1
• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.29
• Product Categories: pharmacetical
• Mol File: 141726-24-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 363.7°C at 760 mmHg
• Flash Point: 136.5°C
• Appearance: /
• Density: 1.052g/cm³
• Vapor Pressure: 1.77E-05mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 1-PHENYLNON-7-YNE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYLNON-7-YNE-1,3-DIONE(141726-24-1)
• EPA Substance Registry System: 1-PHENYLNON-7-YNE-1,3-DIONE(141726-24-1)

Safety Data

• Hazardous Substances Data: 141726-24-1(Hazardous Substances Data)

Usage

Physical state

Yellow crystalline solid

Aromatic structure

Unique arrangement of atoms that creates stability due to resonance

Triple bond

A covalent bond between three atoms (a carbon-carbon triple bond in this case)

Diketone functional group

Two carbonyl groups (C=O) separated by a methylene group (-CH2-)

Reagent use

Utilized in various chemical reactions

Potential applications

Organic synthesis and medicinal chemistry

Distinctive structure

Combination of triple bond and diketone group contributes to its unique properties

Reactivity

Valuable for creating novel compounds and studying reaction mechanisms

InChI:InChI=1/C15H16O2/c1-2-3-4-8-11-14(16)12-15(17)13-9-6-5-7-10-13/h5-7,9-10H,4,8,11-12H2,1H3

Upstream product

• 18719-27-2 5-bromo-pent-2-yne 
• 93-91-4 1-phenylbutan-1,3-dione 
• 17537-31-4 Acetophenone-methyl-d3 
• 150765-78-9 2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate 
• 98-86-2 acetophenone 
• 1193-55-1 2-methylcyclohexane-1,3-dione 

Relevant articles and documents

Claisen-type condensation of vinylogous acyl triflates

(Chemical Equation Presented) The Claisen-type condensation reaction of cyclic vinylogous carboxylic acid triflates with lithium enolates and their analogues produces acyclic alkynes bearing a 1,3-diketone-type moiety. The present transformation is proposed to proceed via a 1,2-addition of the enolate to the vinylogous acyl triflate, followed by fragmentation of the aldolate intermediate.

Tandem nucleophilic addition/fragmentation reactions and synthetic versatility of vinylogous acyl triflates

A thorough analysis of the chemistry of vinylogous acyl triflates provides insight into important chemical processes and opens new directions in synthetic technology. Tandem nucleophilic addition/C-C bond cleaving fragmentation reactions of cyclic vinylogous acyl triflates 1 yield a variety of acyclic acetylenic compounds. Full details are disclosed herein. A wide array of nucleophiles, such as organolithium and Grignard reagents, lithium enolates and their analogues, hydride reagents, and lithium amides, are applied. The respective reactions produce ketones 2, 1,3-diketones and their analogues 3, alcohols 4, and amides 5. The present reactions are proposed to proceed through a 1,2-addition of the nucleophile to the carbonyl group of starting triflates 1 to form tetrahedral alkoxide intermediates C, followed by Grob-type fragmentation, which effects C-C bond cleavage to yield acyclic acetylenic compounds 2-5 and 7. The potent nucleofugacity of the triflate moiety is channeled through the σ-bond framework of 1, providing direct access to the fragmentation pathway without denying other typical reactions of cyclic vinylogous esters. The synthetic versatility of vinylogous acyl triflates, including functionalization reactions of the cyclic enone core (1 → 6 or 8), is also illustrated.