Synthesis of methyl pyropheophorbide-d derivatives possessing the 3-acyl groups and their electronic absorption spectra

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• 作者：Hitoshi Tamiaki^a ; ^{tamiaki@fc.ritsumei.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Yuki Kimura^a ; ^b ; Hiroaki Watanabe^a ; Tomohiro Miyatake^b
• 关键词：Chlorophyll ; Conformation ; π-Conjugation ; Oxidation ; Substitution effect
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：16 June 2016
• 年：2016
• 卷：72
• 期：24
• 页码：3477-3489
• 全文大小：1570 K

文摘

Methyl 3-acyl-pyropheophorbides-a were prepared by modification of naturally occurring chlorophyll-a through Grignard or Barbier reactions of the 3-formyl group and successive Ley–Griffith or Dess–Martin oxidations of the resulting secondary alcohols. The semi-synthetic 3-acyl-chlorins gave intense visible bands in dichloromethane and the absorption spectra were dependent on the 3¹-substituents. The larger π-conjugation of the 3-acyl group with the chlorin moiety shifted the visible absorption maxima to longer wavelengths.