79258-51-8

Upstream product

• 772-62-3 3,3,3-trifluoro-1-phenylpropyne 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 867182-59-0 (Z)-3,3,3-trifluoro-2-iodo-1-(4-methoxyphenyl)-1-phenylpropene 

Downstream Products

• 77599-17-8 (E)-3,3,3-trifluoro-1-{4-[2-(2-hydroxyethylamino)ethoxy]phenyl}-1,2-diphenylpropene 

Relevant academic research and scientific papers

Highly regio- and stereo-selective carbometallation reaction of fluorine-containing internal acetylenes with organocopper reagents

The carbometallation reactions of fluoroalkylated internal alkynes with various organocopper reagents derived from organolithium, Grignard, and organozinc reagents were examined. All carbocupration reactions proceeded smoothly in a highly regio- and stereo-selective manner to give the corresponding vinylcopper intermediates. The intermediates reacted with H + smoothly, leading to the trisubstituted alkenes in high to excellent yields, whereas they reacted only with strictly limited carbon electrophiles such as allyl-, crotyl-, methallyl bromide, etc, probably due to the low reactivity exerted by an electron-withdrawing fluoroalkyl group. Treatment of vinylcopper with iodine resulted in a high yield of the corresponding vinyl iodide, which was employed successfully for Suzuki-Miyaura and Sonogashira cross-coupling reactions. In addition, two key reactions, the carbocupration and the Suzuki-Miyaura cross-coupling reaction realized the first highly stereoselective total synthesis of anti-estrogen drug, panomifene.

A facile stereocontrolled approach to CF3-substituted triarylethenes: Synthesis of panomifene

The stereoselective preparation and Pd-catalyzed cross-coupling reaction of boronates 2 provides a new general and convenient route to CF 3-substituted triaryl ethenes 3, in which the CF3 and Ar3 groups are cis to each other. The synthetic potential was demonstrated by the total synthesis of panomifene (Ar1 = Ar 3 = Ph, Ar2 = 4-(OHCH2CH2NHCH 2CH2O)-C6H4). Bpin = (pinacolato)boryl.

A highly regio- and stereoselective carbocupration of fluoroalkylated internal alkynes: A short total synthesis of the antiestrogenic drug panomifene

(Equation presented) A highly regio- and stereoselective carbometalation reaction of fluoroalkylated internal alkynes with organocopper reagents is described. This reaction is utilized successfully in the short, stereoselective total synthesis of the antiestrogenic drug panomifene.

1,1,2-triphenylpropane and -propene derivatives

A novel 1,1,2-triphenylpropene derivative, namely: STR1 acts on the endocrine system of rats. It exerts oestrogenic or antioestrogenic effects of varying strength in rats, and furthermore inhibits the growth of the mammary tumor induced by 7,12-dimethyl-benz(a)anthracene in rats.