116544-98-0

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 104-55-2 3-phenyl-propenal 
• 100-52-7 benzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 

Downstream Products

• 1272633-25-6 4-benzyl-2-phenylfuran 
• 1355676-74-2 (2E,4Z,6E)-methyl 6-formyl-3-methyl-7-phenylhepta-2,4,6-trienoate 
• 1355676-87-7 (2E,4Z,6E)-methyl 6-formyl-3,5-dimethyl-7-phenylhepta-2,4,6-trienoate 
• 1355676-95-7 (2Z,4Z,6E)-methyl 6-formyl-3,7-diphenylhepta-2,4,6-trienoate 
• 1355677-35-8 (2Z,3Z,5E)-ethyl 2-benzylidene-5-formyl-6-phenylhexa-3,5-dienoate 
• 1355676-75-3 (S,E)-methyl 2-(4-benzylidene-1-methyl-5-oxocyclopent-2-enyl)acetate 
• 1355677-15-4 (S,E)-methyl 2-(4-benzylidene-1,3-dimethyl-5-oxocyclopent-2-enyl)acetate 
• 1355677-22-3 (S,E)-methyl 2-(4-benzylidene-5-oxo-1-phenylcyclopent-2-enyl)acetate 
• 1355677-29-0 C₁₅H₁₄O₃ 

Relevant academic research and scientific papers

Halogen bonding in (Z)-2-iodocinnamaldehyde

Based on the bulkiness of the iodine atom, a non-planar conformation was expected for the title compound. Instead, its molecular structure is planar, as experimentally determined using single crystal X-ray diffraction, and confirmed theoretically by DFT calculations on the single molecule and the halogen pair paired molecules, therefore ruling out crystal packing forces as a principal factor leading to planarity. Indeed, planarity is ascribed to the carbonyl double bond, as when this bond is saturated on forming the related alcohol derivative, the molecule loses planarity. The X-ray molecular structure shows an intermolecular separation between the iodine and the oxygen of the carbonyl shorter than the corresponding van der Waals distance suggesting a weak halogen bond interaction. DFT minimization of this 2-molecule arrangement shows the iodine - oxygen distance much shorter than that observed in the crystal interaction and confirming its stronger halogen bond nature. A trend between increasing I···O(carbonyl) separation and decreasing C-I···O(carbonyl) angle is demonstrated, further confirming the existence of a halogen bond.

Platinum(IV)-catalyzed regioselective synthesis of highly substituted 4H-cyclopenta[b]furans via cascade heterocyclization of 2-(1-alkynyl)-3-aryl-2- propenals with arylet

A platinum-catalyzed cascade heterocyclization and formal [3+2] cycloaddition reaction of 2-(1-alkynyl)-3-aryl-2-propenals and arylethenes has been developed. This cyclization reaction shows excellent regioselectivity to obtain highly substituted 4H-cyclo

One-pot synthesis of α-iodo-substituted α,β-unsaturated aldehydes from propargylic alcohols

(Chemical Equation Presented) An efficient one-pot method for the preparation of α-iodosubstituted α,β-unsaturated aldehydes (α-iodoenals) from propargylic alcohol is developed. The reaction proceeds via an iodoallene intermediate, which is generated in s

Synthesis of Ethyl (2E)-5-Phenylpent-2-en-4-ynoate

An efficient procedure has been developed for the synthesis of ethyl (2E)-5-phenylpent-2-en-4-ynoate by olefination-dehydrohalogenation of (2Z)-2-iodo-3-phenylprop-2-enal prepared by iodination of commercially available cinnamaldehyde.

Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions

A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).

Selectfluor-mediated mild oxidative halogenation and thiocyanation of 1-aryl-allenes with TMSX (X = Cl, Br, I, NCS) and NH4SCN

Presence of TMSX (X = Cl, Br, I) unleashes the oxidative character of Selectfluor and provides a mild dihalogenation method for 1-arylallenes. Preference for 2,3-addition was observed with TMSCl in MeCN irrespective of the nature of the substituent on the aryl moiety, whereas 1,2-addition was preferred in [BMIM][BF4]. With TMSBr and TMSI only products corresponding to 2,3-addition were observed. Reactions carried out with TMSBr in IL solvents gave the corresponding monobromoalkenes as a major product along with the isomeric dibromo-alkenes. Reaction with NH4SCN provided convenient access to dithiocyanate derivatives. The same products were formed via TMS-NCS/Selectfluor. Formation of common products via TMSNCS and NH 4SCN points to the formation and interplay of SCN+/ NCS+ as incipient electrophiles.

Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes

Various 2-alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold-catalyzed transformation was investigated. The use of AuI catalysts bearing carbene ligands, of either the N-heterocyclic carbene or nitrogen acyclic carbene type, delivered the desired products with low catalyst loadings and under very mild reaction conditions. A broad array of substrates was tested, including alkyl-, alkenyl-, and aryl-substituted alkynes, as well as substrates with two alkynyl moieties. The methodology turned out to have a broad scope. Secondary allyl alcohols were also tolerated, and the resulting trisubstituted furans could be isolated in high yields. Easily accessible 2-alkynylallyl alcohols were transformed into highly substituted furans under very mild reaction conditions by the use of gold(I)-carbene catalysts. A broad range of substrates could be transformed in high yields and within short reaction times.

α-Bromination of linear enals and cyclic enones

Facile α-bromination of cyclic enones and linear enals involving N-bromosuccinimide and 1-2 equiv of pyridine-N-oxide is reported herein. α-Bromination of linear enals was found to proceed with double bond geometry retention.

Cascade radical synthesis of heteroarenes via iminyl radicals

A novel cascade cyclisation protocol has been developed which 'zips up' two rings to form new tetracycles. In the protocol, treatment of vinyl bromides and iodides with hexamethylditin (Me3Sn· yields intermediate vinyl radicals which undergo 5-exo cyclisation onto nitrile groups to yield intermediate iminyl radicals. The iminyl radicals can undergo 6-endo cyclisation (or 5-exo followed by neophyl rearrangement) to yield tetracyclic π-radicals which lose hydrogen (H·) in an H-abstraction step. Methyl radicals, generated from the breakdown of trimethylstannyl radicals (Me3Sn·), are proposed as a possible H-abstractor for this final oxidative step. The protocol has been used to synthesise the tetracyclic rings A-D (tetracycle indolizino[1,2-b]quinolin-9(11H)-one) of the anticancer alkaloids camptothecin, mappicine, nothapodytine B and nothapodytine A. The protocol has also been applied to the synthesis of analogues of camptothecin in which ring A has been replaced by thiophene (8,10-dihydrothieno[2′,3′:5,6]pyrido[2,3-a]indolizin-8-one) and ring D by pyrrole (10H-pyrrolizino[1,2-b]quinoline) and benzene (11H-indeno[1,2-b]quinolin-11-one).

Synthesis of heteroarenes via radical cyclisation onto nitriles

A new protocol for the synthesis of tetracyclic nitrogen heteroarenes using cascade radical cyclisation has been developed. The key steps involve 5-exo vinyl radical cyclisation onto nitriles to yield intermediate iminyl radicals which cyclise onto an arene rings. Rings A-D of the anticancer alkaloids camptothecin, mappicine and nothapodytines A and B have been synthesised using this protocol.