25409-10-3

Basic information

• Product Name: 2-Hexanone, 3-methylene- (8CI,9CI)
• Synonyms: 2-Hexanone, 3-methylene- (8CI,9CI)
• CAS NO: 25409-10-3
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.16958
• Product Categories: ACETYLGROUP
• Mol File: 25409-10-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Hexanone, 3-methylene- (8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hexanone, 3-methylene- (8CI,9CI)(25409-10-3)
• EPA Substance Registry System: 2-Hexanone, 3-methylene- (8CI,9CI)(25409-10-3)

Safety Data

• Hazardous Substances Data: 25409-10-3(Hazardous Substances Data)

Upstream product

• 4339-05-3 3-methylhex-1-yn-3-ol 
• 50-00-0 formaldehyd 
• 591-78-6 n-hexan-2-one 
• 506-59-2 N,N-dimethylammonium chloride 
• 74-88-4 methyl iodide 
• 1070-13-9 2-methylidenepentanal 
• 917-54-4 methyllithium 
• 110-62-3 pentanal 

Downstream Products

• 79980-77-1 (S)-(+)-3-methylhexan-2-one 
• 355374-26-4 (R)-3-methyl-2-hexanone 
• 1499-65-6 (1S_.2S)-1.2-Dimethyl-pentanol-⁽¹⁾ 
• 354530-02-2 3-methylhexan-2-ol 

Relevant articles and documents

Cascade Michael addition/cycloketalization of cyclic 1,3-dicarbonyl compounds: Important role of the tethered alcohol of α,β-unsaturated carbonyl compounds on reaction rate and regioselectivity

Reactions of α,β-unsaturated aldehydes and cyclic 1,3-dicarbonyl compounds proceed primarily by cascade Knoevenagel condensation/six-π-electron electrocyclization (K6EC, formal [3 + 3] cycloaddition), while α,β-unsaturated ketones usually react with cyclic 1,3-dicarbonyl compounds in a 1,4-addition manner. This paper discloses our findings that under acidic conditions, α,β-unsaturated carbonyl compounds (ketones and aldehydes) with a tethered alcohol react with cyclic 1,3-dicarbonyl compounds in a highly regioselective 1,4-addition fashion via in situ generation of a hypothetical α-methylene cyclic oxonium ion as the reactive Michael acceptor. Our studies uncovered the important effect of the tethered alcohol on the reaction rate and/or efficiency and some new mechanistic aspects of the cascade Michael addition/cycloketalization. Finally, the substrate scope was examined, and 43 analogues of penicipyrone and tenuipyrone were prepared in good to excellent yields.

Baker's yeast reduction of α-methyleneketones

The bioreduction of α-methyleneketones, R1C(=O)C(=CH2)R2 (R1 = Me, Et, Pr, iso-Bu, Ph, CH2CH2Ph; R2 = Cl, Me, Et, n-Pr, iso-Pr, n-Bu, n-C6H13, Ph, CH2Ph), was mediated by baker's yeast (Saccharomyces cerevisiae) to obtain the corresponding α-methylketones. The R1 and R2 groups had a significant influence on the rate and enantioselectivity of the reductions. The rate of C=C bond reduction was higher than that of C=O bond reduction. Only α-methyleneketones having R1 = Me yielded α-methylketones in high enantioselectivity with e.e.s of 88-99%.

1-Substituted-1-oxo-prostane-derivatives of the E, A and F series

The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E, F, or A series having on the terminal methylene carbon of the alpha chain, a substituent selected from the group consisting of: STR1 wherein R is C1 to C6 alkyl, and phenyl or phenyl substituted with one or more substituents selected from the group consisting of C1 -C4 alkyl, OR16, SR16, F, or Cl, and R16 is C1 to C6 alkyl.