53699-46-0Relevant academic research and scientific papers
Atropisomeric transition state analogs
Ritzeler, Olaf,Parel, Serge,Therrien, Bruno,Bensel, Nicolas,Reymond, Jean-Louis,Schenk, Kurt
, p. 1365 - 1372 (2000)
Transition state mimicry is one of the most powerful concepts in enzyme inhibitor design and has led to the development of catalytic antibodies. Transition state analogs are compounds with a fixed shape that resemble the geometry and charge distribution of the transition state of a given reaction. Stabilization of a transition state like conformation is most often achieved by incorporating a ring system into the analog. We show herein that atropisomerism can be used as a new principle for enforcing a transition state like conformation. Atropisomerism relates to the existence of stereoisomers of structurally constrained molecules due to a frozen rotation about a single bond, as for example in binaphthol. The 1- aminomethylnaphthalene derivative 1 exhibits atropisomerism due to a frozen rotation about the C(1)-C(methylene) single bond, which holds the dihedral angle θ[C(2)-C(1)-C(methylene)N] close to 90°. Compound 1 mimics the transition state for hydride transfer between 1,4-dihydroquinolines 4 and acetone.
Unexpected novel rearrangement reaction: Synthesis of benzo-medium-ring anhydride
Dong, Wen-Liang,Zhao, Bao-Xiang,Wei, Fang,Zuo, Hua,Shin, Dong-Soo
, p. 1224 - 1235 (2008/09/18)
When we attempted to synthesize (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)- 4-(propan-2-ylidene)-dihydrofuran-2,5-dione, we found a novel rearrangement and obtained the unexpected compound that is assigned as benzo-medium-ring anhydride instead of the expected compound. We described the novel rearrangement and a potential method for the synthesis of benzo-medium-ring anhydride derivatives. Copyright Taylor & Francis Group, LLC.
Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreaction of 3-Benzylfuran-2(5H)-ones; Cyclisation to Indenofuranones
Muraoka, Osamu,Tanabe, Genzoh,Sano, Kyohko,Minematsu, Toshie,Momose, Takefumi
, p. 1833 - 1846 (2007/10/02)
The effect of substitution at the 'central methane' on the photoreactivity of 3-benzylfuran-2(5H)-ones 5a-g was investigated.Despite its di-?-methane structure, photochemical arylation was effected to give substituted indenofuranones 6 in good yields.Only
