13732-87-1

Upstream product

• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 
• 74-86-2 acetylene 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 132118-12-8 (Z)-3-(2-Chloro-phenyl)-3-phenyl-propenal 
• 132118-11-7 (E)-3-(2-Chloro-phenyl)-3-phenyl-propenal 
• 96158-84-8 (-)-1,6-diphenyl-1,6-di(o-chlorophenyl)-2,4-hexadiyne-1,6-diol 
• 13732-87-1 (R)-(-)-phenyl-1-(o-chlorophenyl)prop-2-yn-1-ol 
• 118203-46-6 (S)-1-(2-Chloro-phenyl)-1-phenyl-prop-2-yn-1-ol; compound with (S)-2-methyl-piperazine 
• 140160-13-0 1-(2-Chloro-phenyl)-3-{4-[3-(2-chloro-phenyl)-3-hydroxy-3-phenyl-prop-1-ynyl]-phenyl}-1-phenyl-prop-2-yn-1-ol; compound with cyclohex-2-enone 
• 86436-16-0 (R)-1-(2-chlorophenyl)-1-phenylprop-2-yn-1-ol 
• 10473-93-5 N,N-Dimethyl-carbamidsaeure-<1-(2-chlor-phenyl)-1-phenyl-propin-(2)-ylester> 

Relevant academic research and scientific papers

Convenient and highly efficient routes to 2 H-chromene and 4-chromanone derivatives: Iodine-promoted and p-toluenesulfonic acid catalyzed cascade cyclizations of propynols

A convenient strategy is presented for the easy preparation of a series of 2 H-chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4-chromanones can be synthesized through a p-toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99%). Our developed reaction systems are proven to have good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. These systems also provide a new synthetic strategy for two types of important flavonoid skeleton without using costly and toxic metal catalysts. Additionally, the resulting halides could be further exploited in subsequent palladium-catalyzed coupling reactions, so these compounds could act as potential intermediates for the construction of some valuable drug molecules.

Synthesis of sparteine-like chiral diamines and evaluation in the enantioselective lithiation-substitution of N-(tert-butoxycarbonyl)-pyrrolidine

Three chiral diamines were synthesised and evaluated as sparteine surrogates in the lithiation-substitution of N-(tert-butoxycarbonyl)pyrrolidine. The synthesis and attempted resolution of sparteine-like diamines {(1S*, 2R*, 8R*)-10-methyl-6,10-diazatricyclo [6.3.1.02,6]dodecane and (1S*, 2R*, 9R*)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]tridecane} (via inclusion complex formation) are reported. Unfortunately, it was only possible to resolve the diazatricyclo-[7.3.1.02,7] tridecane compound. An alternative route to (1R,2S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02.7]tridecane starting from the natural product, (-)-cytisine, is described. This simple three-step route furnished gram-quantities of a (+)-sparteine surrogate. X-ray crystallography of an intermediate in the route, (1R,5S,12S)-3-methoxycarbonyl-decahydro-1,5-methanopyrido [1,2-a][1,5]diazocin-8-one, enabled the stereochemistry of all of the tricyclic diamines described in this paper to be unequivocally established. Two other diamines, starting from (S)-proline and resolved 2-piperidine ethanol, were prepared using standard methods. These diamines lacked the bispidine framework of (-)-sparteine and were found to impart vastly inferior enantioselectivity. It was concluded that, for the asymmetric lithiation-substitution of N-Boc pyrrolidine, a rigid bispidine framework and only three of the four rings of (-)-sparteine are needed for high enantioselectivity. Furthermore, it is shown that diamine (1R,2S,9S)-11-methyl-7,11-diazatricyclo [7.3.1.02,7]tridecane is the first successful (+)-sparteine surrogate.

Optically active propargyl alcohol derivative and a method for preparation of the same

An optically active propargyl alcohol derivative of the formula (I) STR1 wherein X=phenyl or thienyl and R=lower alkyl, halogenated methyl, phenyl or substituted phenyl having at least one lower alkyl radical and or halogen atom, is prepared by contacting a racemic modification of l- and d-isomers of the formula (I) with l-brucine in an organic solvent, by separating the resultant deposited diastereomer from a solution containing the resultant other diastereomer in the organic solvent, by decomposing each diastereomer with an aqueous mineral acid solution in the presence of an organic solvent capable of dissolving the corresponding optically active isomer dissociated from the diastereomer and incompatible with water so as to allow the optically active isomer to be dissolved in the water-incompatible organic solvent, and by recovering the optically active isomer from the solution thereof.

Chiral Recognition in Complexes of Tertiary Acetylenic Alcohols and Sparteine; Mutual Optical Resolution by Complex Formation

Tertiary acetylenic alcohols have been resolved efficiently by complex formation with (-)-sparteine, and (+/-)-sparteine was resolved by complex formation with the optically active tertiary acetylenic alcohols; an X-ray structural study of the 1:1 complex of 1-(o-bromophenyl)-1-phenylprop-2-ynol (1d) and (-)-sparteine showed that two hydrogen bonds, CC-H...OH and OH...N, are important in formation of the complex.