1192-88-7Relevant articles and documents
Ho,Wong
, p. 196 (1974)
Synthesis of aldehydes by a one-carbon homologation of ketones and aldehydes via --α,β-unsaturated isocyanides
Moskal, Janusz,Leusen, Albert M. van
, p. 137 - 141 (1987)
Ketones and aldehydes react via a Wittig-Horner-Emmons reaction using diethyl(isocyanomethyl)phosphonate to form α,β-unsaturated isocyanides (4), which are either hydrolyzed as such, under acid conditions, or hydrolyzed after oxidation to α,β-unsaturated isocyanates (6) to give aldehydes containing one additional carbon atom.The scope of the reaction is demonstrated by 20 examples.
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Taber,D.F.,Gunn,B.P.
, p. 450 - 452 (1979)
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Taguchi,H. et al.
, p. 2465 - 2468 (1973)
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Reese,Stebles
, p. 4427 (1972)
Structure-activity relationships of xanthene carboxamides, novel CCR1 receptor antagonists
Naya, Akira,Ishikawa, Makoto,Matsuda, Kenji,Ohwaki, Kenji,Saeki, Toshihiko,Noguchi, Kazuhito,Ohtake, Norikazu
, p. 875 - 884 (2003)
The structure-activity relationships of xanthene carboxamide derivatives on the CCR1 receptor binding affinity and the functional antagonist activity were described. Previously, we reported a quaternarized xanthen-9-carboxamide 1 as a potent human CCR1 receptor antagonist that was derived from a xanthen-9-carboxamide lead 2a. Further derivatization of 2a focusing on installing an additional substituent into the xanthene ring resulted in the identification of 2b-1 with IC50 values of 1.8 nM and 13 nM in the binding assay using human CCR1 receptors transfected CHO cells and in the functional assay using U937 cells expressing human CCR1 receptors, respectively.
Ring Expansion, Ring Contraction, and Annulation Reactions of Allylic Phosphonates under Oxidative Cleavage Conditions
Orr, Dupre,Yousefi, Nikolas,Minehan, Thomas G.
, p. 2839 - 2843 (2018/05/29)
Oxidative cleavage of cycloalkenylalkylphosphonates 1 followed by treatment with base gives rise to homologated cycloalkenones 2 in good to excellent yields. Subjecting cycloalk-2-enylphosphonates 3 to identical conditions provides the one-carbon ring-contracted compounds 4 in excellent yields. Oxidative cleavage of γ,δ-unsaturated ketophosphonates 6 followed by treatment with base affords 2-cyclopenten-1-ones 7 in good overall yields. This method may offer a practical alternative to existing methods for effecting one-carbon ring expansion, ring contraction, and annulation reactions.
Efficient Access to All-Carbon Quaternary and Tertiary α-Functionalized Homoallyl-type Aldehydes from Ketones
Pace, Vittorio,Castoldi, Laura,Mazzeo, Eugenia,Rui, Marta,Langer, Thierry,Holzer, Wolfgang
supporting information, p. 12677 - 12682 (2017/09/08)
β,γ-Unsaturated aldehydes with all-carbon quaternary or tertiary α-centers were rapidly assembled from ketones through a unique synthetic operation consisting of 1) C1 homologation, 2) Lewis acid mediated epoxide–aldehyde isomerization, and 3) electrophilic trapping. The synthetic equivalence of a vinyl oxirane and a β,γ-unsaturated aldehyde is the key concept of this previously undisclosed tactic. Mechanistic studies and labeling experiments suggest that an aldehyde enolate is a crucial intermediate. The homologating carbenoid formation plays a critical role in determining the chemoselectivity.
