3880-50-0Relevant academic research and scientific papers
Synthesis and characterization of acetone hydrazones
Miro Sabate, Carles,Delalu, Henri
experimental part, p. 57 - 63 (2012/03/13)
1-Isopropylidene-2-methylhydrazine (1), 1-isopropylidene-2- hydroxyethylhydrazine (2) and 1-isopropylidene-2-formylhydrazine (3) were synthesized by reaction of the corresponding hydrazine with an excess of acetone in the presence of a drying agent (anhydrous sodium sulfate or barium oxide). All compounds 1-3 were characterized by elemental analysis, coupled gas chromatography-mass spectrometry (GC-MS), multinuclear NMR spectroscopy ( 1H, 13C and 15N) and vibrational spectroscopy (infrared and Raman). Compounds 1 and 2 are liquid at room conditions and their density was measured by means of a picnometer, however, (at room conditions) compound 3 is a solid and its crystal density and structure were determined by low temperature X-ray diffraction techniques (monoclinic, P21/n, Z = 4, a = 5.666(1) A, b = 6.254(1) A, c = 15.277(4) A, β = 91.30(2)°, V = 541.2(2) A3). The structure of hydrazone 3 is discussed in detail and compared to that of monoformylhydrazine. Finally, the (gas phase) structure of compound 3 was optimized using DFT calculations (B3LYP/6-31+G(d, p)) and its NBO charges are reported. Copyright
New straightforward synthesis and characterization of a unique 1β- methylcarbapenem antibiotic biapenem bearing a σ-symmetric bicyclotriazoliumthio group as the pendant moiety
Kumagai, Toshio,Tamai, Satoshi,Abe, Takao,Matsunaga, Hiroshi,Hayashi, Kazuhiko,Kishi, Ikuo,Shiro, Motoo,Nagao, Yoshimitsu
, p. 8145 - 8149 (2007/10/03)
Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2- α][1,2,4]triazolium-6-yl)thio]-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1- methylcarbapen-2-em-3-carboxylate, is a new non-natural 1β-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S- - -O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, 1H NMR, and deuteration experiment analyses.
