134284-28-9Relevant academic research and scientific papers
Ultrasound-assisted Wittig reaction: A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones
Wu, Li-Qiang,Yang, Chun-Guang,Yang, Li-Ming,Yang, Li-Juan
experimental part, p. 47 - 50 (2010/04/05)
A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones is described. Ultrasound-assisted Wittig reaction of alkyltriphenyl phosphonium bromides with o-vanillin in basic aqueous conditions followed by reduction with Na/n-BuOH gave 2-methoxy-6-alkylphenols. Oxidation of 2-methoxy-6-alkylphenols with Fremy's salt produced the title compounds.
Microwave-mediated claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring 1,4-benzoquinones. The first syntheses of verapliquinones A and B and panicein A
Davis, Christopher J.,Hurst, Timothy E.,Jacob, Aouregan M.,Moody, Christopher J.
, p. 4414 - 4422 (2007/10/03)
The naturally occurring 1,4-benzoquinones 2-methoxy-6-propyl-1,4- benzoquinone (1), 2-methoxy-6-pentyl-1,4-benzoquinone (primin 2), 2-methoxy-6-pentadecyl-1,4-benzoquinone (3), 2-methoxy-6-heptadecyl-l,4- benzoquinone (dihydroirisquinone, pallasone B; 4) were synthesized by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 10, followed by hydrogenation of the side chain alkene, and oxidation to the quinone. The Claisen-based methodology was extended to the first synthesis of the marine benzoquinones verapliquinones A and B (5 and 6), and panicein A (7). Isoarnebifuranone (9) was also synthesized by a similar strategy.
The Claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring benzoquinones including an ansa-bridged derivative related to the ansamycin antibiotics
Davis, Christopher J.,Moody, Christopher J.
, p. 1874 - 1876 (2007/10/03)
The naturally occurring benzoquinones primin 1 and pallasone B 2 were synthesised by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 4, followed by hydrogenation of the side chain alkene, and oxidation to the quinon
Synthesis and structure-activity relationships of phaffiaol and related antioxidants
Jinno, Shuji,Okita, Takaaki
, p. 1688 - 1694 (2007/10/03)
Total synthesis of a novel long chain alkyl phenol, phaffiaol (1), a potent antioxidant isolated from Phaffia rhodozyma, was achieved via three reaction steps starting from 3,5-dibromosalicylaldehyde (2). We also prepared several types of long chain alkyl
