150048-35-4

Upstream product

• 931-49-7 1-ethenylcyclohexene 

Downstream Products

• 1262782-93-3 1-adamantyl-4-cyclohexenyl-5-iodo-1H-1,2,3-triazole 
• 1262782-83-1 4-cyclohexenyl-5-iodo-1-((phenylthio)methyl)-1H-1,2,3-triazole 
• 1262782-88-6 1-benzyl-4-cyclohexenyl-5-iodo-1H-1,2,3-triazole 
• 1362970-22-6 (2,3,5,6-tetrafluoropyridyl)-(1-cyclohexenyl)ethyne 
• 57210-38-5 1-(cyclohex-1-en-1-yl)-4-methylpent-1-yn-3-ol 
• 1198362-71-8 1-chloro-2-(cyclohexenyl)-3-iodoanthracene 

Relevant academic research and scientific papers

First total synthesis of naturally occurring (-)-nitidon and its enantiomer

The first total synthesis of naturally occurring (-)-nitidon and its enantiomer is reported. The best of the routes investigated for preparation of these enantiomerically pure compounds involves a modification of the Cadiot-Chodkiewicz reaction and the Sharpless asymmetric epoxidation of an (E)-2-ene-4,6-diyn-1-ol as key steps and proceeds in five steps and 18% overall yield. Both enantiomers of nitidon and some related 6-(1,3-diyn-1-yl)-2H-pyran- 2-ones have been found to exhibit significant cytotoxic activity against human cancer cell lines in vitro. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

Iodination of organotrifluoroborates: Synthesis of vinyl and alkynyl iodides

Vinyl- and alkynyltrifluoroborates are rapidly converted to vinyl and alkynyl iodides under mild conditions using sodium iodide in the presence of chloramine-T. The reaction is stereospecific and proceeds in excellent yield.

Efficient synthesis of 1-iodoalkynes: Via Al2O3 mediated reaction of terminal alkynes and N -iodosuccinimide

Iodination of terminal alkynes using N-iodosuccinimide (NIS) in the presence of γ-Al2O3 was developed to afford 1-iodoalkynes with good to excellent yields (up to 99%). This described approach featured excellent chemoselectivity, good functional group tolerance, and utilization of an inexpensive catalyst.

Efficient synthesis of alkynyl amides via aminocarbonylation of iodoalkynes

Iodoethynylbenzene as iodoalkyne model compound was aminocarbonylated with tert-butylamine under carbon monoxide atmosphere in the presence of in situ palladium(0) catalysts. The formation of the unsaturated carboxamide (alkynyl amide) is always accompanied by that of the Glaser coupling product, diphenylbutadiyne. The yield of the amide-forming reaction was optimised by the systematic variation of the phosphine ligand, carbon monoxide pressure and temperature. The scope of the reaction was investigated by using various primary and secondary amines including amino acid methyl esters as N-nucleophiles. 17α-(Iodoethynyl)-testosterone was also functionalised by using this methodology providing the corresponding 17α-(carboxamidoethynyl)-testosterone derivatives in up to 96% yields. The reaction was extended to 1-(iodoethynyl)cyclohex-1-ene and 1-iodohex-1-yne. Ethyl iodopropiolate gave the enamine type product by the addition of amine to the alkyne functionality which was formed from the iodoalkyne via deiodination under standard aminocarbonylation conditions. The bromo analogue, bromoethynylbenzene has shown lower reactivity than the corresponding iodo derivative.

Facile and efficient synthesis of 1-haloalkynes via DBU-mediated reaction of terminal alkynes and N-haloimides under mild conditions

Directly from terminal alkynes and with N-halosuccinimides (halo = Br and I) or N-cholorophthalimide as the halogen sources, DBU as the activator, 1-haloalkynes were prepared in good to excellent yields at room temperature. Bis(bromoalkyne) and bis(iodoal

Reusable and efficient CuI/TBAB-catalyzed iodination of terminal alkynes in water under air

An environmentally-friendly and operationally-simple process for the synthesis of 1-iodoalk-1-ynes under mild conditions catalyzed by CuI/TBAB in water under air was developed in this study. Catalyst loadings of CuI as low as 1-2 mol% gave 1-iodoalk-1-yne