1232144-31-8

Basic information

• Product Name: 3-(3-chlorophenyl)propiolaldehyde
• Synonyms: 3-(3-chlorophenyl)propiolaldehyde
• CAS NO: 1232144-31-8
• Molecular Weight: 164.591
• Mol File: 1232144-31-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 3-(3-chlorophenyl)propiolaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-chlorophenyl)propiolaldehyde(1232144-31-8)
• EPA Substance Registry System: 3-(3-chlorophenyl)propiolaldehyde(1232144-31-8)

Safety Data

• Hazardous Substances Data: 1232144-31-8(Hazardous Substances Data)

Upstream product

• 766-83-6 m-chlorophenylacetylene 
• 68-12-2 N,N-dimethyl-formamide 
• 587-04-2 m-Chlorobenzaldehyde 
• 1354931-76-2 1-chloro-3-(3,3-diethoxyprop-1-ynyl)benzene 
• 625-99-0 3-iodochlorobenzene 
• 80151-33-3 3-(3-chlorophenyl)prop-2-yn-1-ol, 

Downstream Products

• 1241601-89-7 (E)-3-(3-chlorophenyl)-1-(2-styrylphenyl)prop-2-yn-1-ol 
• 1241602-95-8 (Z)-3-(3-chlorophenyl)-1-(2-(2-methoxyvinyl)phenyl)prop-2-yn-1-ol 
• 1376709-02-2 4-(3-chlorophenyl)-3-(diphenylmethyleneamino)-1-phenylpyridin-2(1H)-one 
• 1402578-57-7 diethyl 2-(3-(3-chlorophenyl)prop-2-ynylidene)malonate 
• 1361017-60-8 C₂₄H₁₅ClFNO 
• 1232144-16-9 (S)-methyl-3-(6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)-3-(3-chlorophenyl)propanoate 

Relevant articles and documents

Catalytic Enantioselective Quick Route to Aldol-Tethered 1,6- and 1,7-Enynes from ω-Unsaturated Aldehydes

An effective asymmetric route to functionalized 1,6- and 1,7-enynes has been developed based on a direct cross-aldol reaction between ω-unsaturated aldehydes and propargylic aldehydes (α,β-ynals) promoted by combined α,α-dialkylprolinol ether/Br?nsted acid catalysis. This synergistic activation strategy is key to accessing the corresponding aldol adducts with high stereoselectivity, both enantio- and diastereoselectivity. The aldol reaction also proceeds well with propargylic ketones (α,β-ynones) thus enabling a stereocontrolled access to the corresponding tertiary alcohols. The utility of these adducts, which are difficult to prepare through standard methodology, is demonstrated by their transformation into trisubstituted bicyclic enones using standard Pauson-Khand conditions.

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

Micelle-Mediated Trimerization of Ynals to Orthogonally Substituted 4H-Pyrans in Water: Downstream Rearrangement to Bioactive 2,8-dioxabicyclo[3.3.1]nona-3,6-diene Frameworks

An efficient trimerization of ynals to diversely substituted 4H-pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid-mediated downstream rearrangement of the derived 4H-pyrans to interesting 2,8-dioxabicyclo[3.3.1]nona-3,6-dienes has been observed.