777882-57-2Relevant academic research and scientific papers
A method of synthesizing chiral alkene propyl alcohol
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Paragraph 0136-0144, (2019/07/04)
The invention discloses a method for synthesizing chiral alkene propyl alcohol method, which belongs to the technical field of organic chemistry. The method adopts the [...] derived binaphthol potassium salt as a chiral [...] catalyst, catalytic [...] pro
Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies
Liu, Yidong,Liu, Song,Li, Dongmei,Zhang, Nan,Peng, Lei,Ao, Jun,Song, Choong Eui,Lan, Yu,Yan, Hailong
, p. 1150 - 1159 (2019/01/11)
The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Br?nsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure-enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Br?nsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Br?nsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.
Porphyrazine with bulky 2-(1-adamantyl)-5-phenylpyrrol-1-yl periphery tuning its spectral and electrochemical properties
Kryjewski, Michal,Tykarska, Ewa,Rebis, Tomasz,Dlugaszewska, Jolanta,Ratajczak, Magdalena,Teubert, Anna,Gapiński, Jacek,Patkowski, Adam,Piskorz, Jaroslaw,Milczarek, Grzegorz,Gdaniec, Maria,Goslinski, Tomasz,Mielcarek, Jadwiga
supporting information, p. 217 - 223 (2015/07/15)
The synthesis and physicochemical properties of a novel porphyrazine possessing an alternate system of two peripheral substituents, 2-(1-adamantyl)-5-phenylpyrrol-1-yl and dimethylamino, are presented. Precursor maleonitriles were characterized using X-ra
Acylguanidines as small-molecule β-secretase inhibitors
Cole, Derek C.,Manas, Eric S.,Stock, Joseph R.,Condon, Jeffrey S.,Jennings, Lee D.,Aulabaugh, Ann,Chopra, Rajiv,Cowling, Rebecca,Ellingboe, John W.,Fan, Kristi Y.,Harrison, Boyd L.,Hu, Yun,Jacobsen, Steve,Jin, Guixan,Lin, Laura,Lovering, Frank E.,Malamas, Michael S.,Stahl, Mark L.,Strand, James,Sukhdeo, Mohani N.,Svenson, Kristine,Turner, M. James,Wagner, Erik,Wu, Junjun,Zhou, Ping,Bard, Jonathan
, p. 6158 - 6161 (2007/10/03)
BACE1 is an aspartyl protease responsible for cleaving amyloid precursor protein to liberate Aβ, which aggregates leading to plaque deposits implicated in Alzheimer's disease. We have identified small-molecule acylguanidine inhibitors of BACE1. Crystallographic studies show that these compounds form unique hydrogen-bonding interactions with the catalytic site aspartic acids and stabilize the protein in a flap-open conformation. Structure-based optimization led to the identification of potent analogs, such as 10d (BACE1 IC50 = 110 nM).
Carbon-carbon bond formation by radical addition-fragmentation reactions of O-alkylated enols
Cai, Yudong,Roberts, Brian P.,Tocher, Derek A.,Barnett, Sarah A.
, p. 2517 - 2529 (2007/10/03)
α-tert-Butoxystyrene [H2C = C(OBut)Ph] reacts with α-bromocarbonyl or α-bromosulfonyl compounds [R 1R2C(Br)EWG; EWG = -C(O)X or -S(O2)X] to bring about replacement of the bromine atom by the phenacyl group and give R 1R2C(EWG)CH2C(O)Ph. These reactions take place in refluxing benzene or cyclohexane with dilauroyl peroxide or azobis(isobutyronitrile) as initiator and proceed by a radical-chain mechanism that involves addition of the relatively electrophilic radical R 1R2(EWG)C* to the styrene. This is followed by β-scission of the derived α-tert-butoxybenzylic adduct radical to give But*, which then abstracts bromine from the organic halide to complete the chain. α-1-Adamantoxystyrene reacts similarly with R 1R2C(Br)EWG, at higher temperature in refluxing octane using dα-tert-amyl peroxide as initiator, and gives phenacylation products in generally higher yields than are obtained using α-tert-butoxystyrene. Simple iodoalkanes, which afford relatively nucleophilic alkyl radicals, can also be successfully phenacylated using α-1-adamantoxystyrene. O-Alkyl O-(tert-butyldimethylsilyl) ketene acetals H2C=C(OR)OTBS, in which R is a secondary or tertiary alkyl group, react in an analogous fashion with organic halides of the type R1R2C(Br)EWG to give the carboxymethylation products R1R2C(EWG)CH 2CO2Me, after conversion of the first-formed silyl ester to the corresponding methyl ester. The silyl ketene acetals also undergo radical-chain reactions with electron-poor alkenes to bring about alkylation-carboxymethylation of the latter. For example, phenyl vinyl sulfone reacts with H2C=C(OBut)OTBS to afford Bu tCH2CH(SO2Ph)CH2CO2Me via an initial silyl ester. In a more complex chain reaction, involving rapid ring opening of the cyclopropyldimethylcarbinyl radical, the ketene acetal H 2C=C(OCMe2C3H5-cyclo)OTBS reacts with two molecules of N-methyl- or N-phenyl-maleimide to bring about [3 + 2] annulation of one molecule of the maleimide, and then to link the bicyclic moiety thus formed to the second molecule of the maleimide via an alkylation-carboxymethylation reaction.
