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3-Butyn-2-one was used in the synthesis of clerodane diterpenoid (+/-)-sacacarin. It was used as substrate in stereoselective, conjugate arylation mediated by gallium(III) chloride leading to (E)-α,β-unsaturated ketones. 3-Butyn-2-one undergoes asymmetric double-Michael reaction with ortho-tosylamidophenyl malonate catalyzed by chiral aminophosphines to yield indolines2. It undergoes double Michael reaction with nitrogen-containing tethered diacid to give pipecolic acid derivatives. 3-Butyn-2-one, is used as a reactant with Dimethyl acetone-1,3-dicarboxylate, under mild conditions to give a benzenoid product via a Michael addition - aldol cyclization process.
H Monti.; G Audran.; G Léandri.; JP Monti. ZnI 2 Catalyzed [2+ 2] versus [3+ 2] cycloaddition of an allyltrimethylsilane with 3-butyn-2-one: Confirmation of a cyclobutene by-product formation. Tetrahedron letters. 1994, 35,(19), 3073-3076.
IH Um.; EJ Lee.; JS Min. Remarkable catalytic effect of H+ in Michael-type additions of anilines to 3-butyn-2-one. Tetrahedron letters. 2001, 57,(47), 9585-9589.
Reacts with Dimethyl acetone-1,3-dicarboxylate, A14969, under mild conditions to give a benzenoid product via a Michael addition - aldol cyclization process: Synth. Commun., 28, 1525 (1998):
For a similar reaction, see Methyl 2-hexynoate, B23065.
Hazard Statements: H225-H300-H315-H318-H335
Highly flammable liquid and vapour. Fatal if swallowed. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.
Precautionary Statements: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.