1203669-21-9

Basic information

• Product Name: 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one
• Synonyms: 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one
• CAS NO: 1203669-21-9
• Molecular Weight: 315.166
• Mol File: 1203669-21-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one(1203669-21-9)
• EPA Substance Registry System: 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one(1203669-21-9)

Safety Data

• Hazardous Substances Data: 1203669-21-9(Hazardous Substances Data)

Upstream product

• 1357394-80-9 1-(2-bromophenyl)-3-(4-methoxyphenyl)-prop-2-yn-1-ol 
• 7154-66-7 2-bromobenzoic acid chloride 
• 768-60-5 4-methoxyphenylacetylen 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1516898-04-6 C₁₈H₁₀Br₂N₂O₄ 
• 88-65-3 2-bromobenzoic-acid 

Downstream Products

• 1203669-37-7 2-(4-methoxyphenyl)-1-phenylquinolin-4(1H)-one 
• 246181-55-5 1-methyl-2-(4’-methoxyphenyl)-1H-4-quinolone 
• 1516898-18-2 C₁₇H₁₆BrNO₂ 
• 893-10-7 2-(4'-methoxyphenyl)-4H-1-benzothiopyran-4-one 
• 3813-92-1 2-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline 

Relevant articles and documents

Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt

Inspired by naturally occurring molecules containing atropisomeric N+-C axes, we have developed a novel synthetic approach to generate a library of axially chiral N-aryl quinolinium salts. Enantiopurities up to 93 % ee were obtained via a four-step route from commercially available precursors. Axial stereochemistry was controlled through an enantioselective ring-closing Buchwald–Hartwig coupling reaction. The structure and properties of the salts were examined by X-ray crystallography, DFT, UV-Vis, and fluorescence spectroscopy, revealing high rotational barriers and solvatochromic behaviour.

QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF

The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]

Synthesis of Dibenzotropones by Alkyne-Carbonyl Metathesis

Dibenzocycloheptanones (dibenzotropones) were prepared by Br?nsted acid mediated intramolecular alkyne-carbonyl metathesis (ACM) reactions. The cyclization precursors are readily available by Sonogashira reaction of 2-bromobenzoyl chloride with terminal alkynes, followed by Suzuki reactions with benzaldehydes. The ACM reactions are highly modular and atom economic and allow for the construction of two regioisomeric series of dibenzotropones.

Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives

An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.

Nitromethane as a Carbanion Source for Domino Benzoannulation with Ynones: One-Pot Synthesis of Polyfunctional Naphthalenes and a Total Synthesis of Macarpine

A one-pot, transition-metal-free, domino Michael/SNAr protocol of general applicability has been devised for the regioselective synthesis of polyfunctional naphthalenes by employing nitromethane and ortho-haloaryl ynones. Utilization of nitromethane as a one carbon carbanion source that is incorporated into a variety of ynones, ends up as an aromatic nitro substituent. The application of this domino process towards a total synthesis of the polycyclic alkaloid macarpine demonstrate for the efficacy of this methodology. The conceptually simple approach to affect regioselective, multifunctional benzoannulation of ynones displays wide substrate scope and functional-group tolerance and has been implemented with substituted nitromethanes, as well as with alicyclic o-haloynones.

Base-mediated insertion reaction of alkynes into carbon-carbon σ-bonds of ethanones: synthesis of hydroxydienone and chromone derivatives

Transition-metal free insertions of alkynes into carbon-carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.

Base-Promoted Tandem Reaction towards Conjugated Dienone or Chromone Derivatives with a Cyano Group: Insertion of Alkynes into C–C σ-Bonds of 3-Oxopropanenitriles

Base-promoted insertion reactions of alkynes into the C–C σ-bonds of α-cyano ketones were established to construct highly functionalized conjugated olefins or chromone derivatives via transition metal-free tandem reactions. These reactions are initialized through the nucleophilic attack of α-cyano ketones to alkynones followed by intramolecular nucleophilic addition/ring-opening to furnish the cyano-containing alkenes. In the cases of alkynones bearing an ortho-halide-substituted aryl ring, a further C–O bond coupling reaction occurs to afford chromone derivatives in good to high yields. Various alkynones bearing alkyl or aryl substituents were compatible in the reaction. This reaction has the potential to become a general synthetic protocol for the preparation of cyano-substituted olefins and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups. (Figure presented.).

Stitching Oxindoles and Ynones in a Domino Process: Access to Spirooxindoles and Application to a Short Synthesis of Spindomycin B

A general, transition-metal-free, one-pot, domino Michael-SNAr or AdNE substitution protocol was devised for spiroannulation of oxindoles with ortho-bromoaryl ynones, β-bromoalkenyl ynones, and β-bromoalkenyl enones in a convenient a