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Knoevenagel Reaction of Pyropheophorbide and Synthesis of Its Heterocyclo-substituted Derivatives
Wang, Jinjun,Wu, Xuran,Han, Guangfan,Shen, Rongji 科學出版社 2005 CHINESE JOURNAL OF ORGANIC CHEMISTRY Vol.25 No.3
<P>Methyl pyropheophorbide-c? was used as starting material and the Knoevenagel reaction of the aldehyde group on pyropheophorbide with active methylene group in /?-diketone, a-cyanoketone or malono-nitrile was carried out to complete the synthesis of derivatives of methyl pyropheophorbide-a substituted with five-membered heterocycle at 3-positipon. The structures of all these new compounds were characterized by elemental analysis, UV, IR and LH NMR spectra.</P>
WANGJinJun,JIJianYe,JINGJiRong,LIJiaZhu,HANGuangFan,SHIMYoung, Key 科學出版社 2006 CHINESE JOURNAL OF ORGANIC CHEMISTRY Vol.26 No.4
From methyl pyropheophorbide-a (1), the aldehyde chlorin 2 was obtained by the protection of ring-E and oxidation of vinyl group at 3-position. Grignard reaction with long chain alkyl magnesium bromide converted the formyl group into the acyl group. The hydroxyl group of sec-alcohol chlorin 3 was oxidized by mixed oxidizing agent consisting of tetrapropylammonium perruthenate and N-methylmorpholine N-oxide to generate 3-acyl pyropheophorbide-a derivative 4. The Grignard reaction of which with long chain alkyl magnesium bromide was carried out to yield tertiary alcohol chlorin 5 as nucleophilic adduct and chlorin 3 as reduced product. The following dehydration of alcohol chlorin 3 or 5 was performed in the dry benzene at reflux to form trans-form methyl pyropheophorbide-a substituted with mono- or di-long chain alkyl group at 3-position 6 or 7, respectively. The structures of all new compounds were characterized by elemental analysis, UV, IR and ^1H NMR spectra.