CAS: 21959-36-4; (S)-Ethyl 2-Acetamido-3-(4-Hydroxy-3,5-Diiodophenyl)Propanoate

主要参考文献

参考标题:Synthesis Of Thyroxine: Biomimetic Studies
作者:Natalie V. Bell,W. Russell Bowman,Paul F. Coe,Andrew T. Turner,Del Whybrow |发布日期:1997.6.1
摘要:The Biomimetic Oxidative Coupling Of The Ethyl Ester Of N-Acetyl-3,5-Diiodotyrosine (1) To Yield The Ethyl Ester Of N-Acetylthyroxine (2) Has Been Investigated. A Putative Mechanism Involving Phenolic Coupling To Yield An Intermediate Aryloxydienone (7) Followed By An E2 Elimination For Loss Of The Side Chain Has Been Proposed. Oxidative Couplings With Analogous 4-Substituted 3,5-Diiodophenols Indicate That A Number Of Mechanisms Are Possible; These Include Quinone Methide Intermediates And Sn2 Substitutions In The Intermediate Aryloxydienones. Rearomatization Of The Intermediate Aryloxydienones Is A Strong Driving Force For The Loss Of The Side Chains. The Results Indicate That 3,5-Diiodo-4-Aryloxydienones Are Good Leaving Groups In E2 And Sn2 Mechanisms. The Synthetic Method Provides A Facile Synthesis Of Thyroxine Analogues From Readily Available 4-Substituted 3,5-Diiodophenols. Keywords: Diiodotyrosine, Phenolic Coupling, Phenoxyl Radicals, Thyroxine.

合成参考文献

参考文献:10.1007/978-3-662-61017-6_6
参考文献:10.1055/s-0030-1258379
摘要:Qiao J, Lam P. Copper-Promoted Carbon-Heteroatom Bond Cross-Coupling with Boronic Acids and Derivatives. Synthesis. 2010 Dec 22;2011(06):829–56. doi: 10.1055/s-0030-1258379.