77599-17-8

Usage

Uses

Used in Pharmaceutical Industry:
Panomifene is used as an antiestrogen for the treatment of breast cancer. It functions by targeting estrogen receptors, thereby inhibiting the growth of cancer cells that rely on estrogen for proliferation.
Additionally, due to its similarity with tamoxifen, Panomifene may also be utilized in research and development for understanding the mechanisms of action and potential improvements in antiestrogen therapies.

InChI:InChI=1/C25H24F3NO2/c26-25(27,28)24(21-9-5-2-6-10-21)23(19-7-3-1-4-8-19)20-11-13-22(14-12-20)31-18-16-29-15-17-30/h1-14,29-30H,15-18H2/b24-23+

Upstream product

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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 highly stereoselective preparation of CF3-substituted 1-aryl-1,2-diphenylethenes: Application to the synthesis of panomifene

β-CF3-α,β-diphenylvinyl sulfide 3a was prepared stereoselectively in 77% yield from the reaction of 2 with phenyllithium at room temperature for 5 h. Oxidation of 3a with MCPBA afforded the corresponding vinyl sulfone 4a, in which (E)-4a can be

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.

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.

New practical synthesis of panomifene. The effect of 2-trifluoromethyl substituent on the stereoselectivity of dehydration of 1,1,2-triarylethanols

Highly stereoselective eliminations were achieved by acid-catalysed dehydration of 1-(4-alkoxy)-3,3,3-trifluoro-1,2-diphenylpropan-1-ols (10, 11, 15). The influence of the trifluoromethyl group on the stereochemistry of the elimination has been discussed. The observed high stereoselectivity has been applied to give a new, practical synthesis of antiestrogenic drug panomifene (1).