CAS: 106268-96-6; (R)-(2-Methyloxiran-2-yl)Methyl 4-Nitrobenzoate

相似化合物

120-48-9 99-77-4 16397-70-9

上下游产品

4-nitro-benzoyl chloride 3-hydroxy-2-methyl-1-propene 2-methylglycidol (R)-2-methylglycidol (R)-3-(Dimethylamino)-2-methylpropane-1,2-diol (S)-(+)-2-methyl-1-(phenylthio)-2,3-propanediol (S)-2-methylglycidol 4-nitro-benzoic acid

📜2-甲基-2,3-环氧基-1-丙醇,4-硝基苯甲酰氯置于三乙胺体系中,用 乙醚 用作溶剂,化学反应 1.0H,以82%的收率获得(2R)-(-)-2-甲基-4-硝基苯甲酸缩水甘油酯
参考文献:Syntheses,Structures,And Enzymic Evaluations Of Conformationally Constrained,Analog Inhibitors Of Carnitine Acetyltransferase: (2R,6R)-,(2S,6S)-,(2R,6S)-,And (2S,6R)-6-(Carboxylatomethyl)-2-(Hydroxymethyl)-2,4,4-Trimethylmorpholinium
标题:Syntheses,Structures,And Enzymic Evaluations Of Conformationally Constrained,Analog Inhibitors Of Carnitine Acetyltransferase: (2R,6R)-,(2S,6S)-,(2R,6S)-,And (2S,6R)-6-(Carboxylatomethyl)-2-(Hydroxymethyl)-2,4,4-Trimethylmorpholinium
摘要:The Syntheses And Structures Of The Four Stereoisomers Of 6-(Carboxylatomethyl)-2-(Hydroxymethyl)-2,4,4-Trimethylmorpholinium,1,Are Described. The Key Step In The Synthetic Strategy Involves An Intramolecular Michael Addition Reaction. Condensation Of Nonracemic 3-(Methylamino)-2-Methylpropane-1,2-Diol,3,With Methyl 4-Bromo-2-Butenoate Followed By Intramolecular Michael Addition Gives A Mixture Of Two Diastereomers Of Methyl 2-[4,6-Dimethyl-6-(Hydroxymethyl)Morpholinyl]-Acetate,5. The Diastereomeric Ratio Ofthe Products In This Reaction Changes From 6:1 To 1:1 With A Change In Solvent Fi Om Diethyl Ether:Methanol (35:1,V:V) To Methanol. The Structures And Absolute Configurations Of 1 Were Determined By Single Crystal X-Ray Analyses. In Crystals And Solution,The Morpholinium Rings Adopt A Chair Conformation With Carboxylatomethyl occupying An Equatorial Position. All Four Stereoisomers Inhibit Pigeon Breast Carnitine Acetyltransferase (Cat). Of This Series,(2S,6R)-1 Binds To Cat Most Strongly With A Ki Of 190 +/-20 Mu M And An Ic50 Of 0.42 Mm. The Enzymatic Assays Of 1 Confirm That Cat Recognizes Both Configurations At C2 And C6 In The Analogues. Cat Has A Different Conformation When It Binds Carnitine Or Acetylcarnitine Than When It Binds 1. This Latter Conformation May Resemble That When Cat Catalyzes Acetyl Transfer.
Doi:10.1021/jo00126A018