6308-92-5Relevant academic research and scientific papers
Synthetic method for cis-1,4-cyclohexanediol
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Paragraph 0055-0059, (2018/03/24)
The invention discloses a synthetic method for cis-1,4-cyclohexanediol, belonging to the field of organic chemical synthesis. According to the method, 4-(alkylacyloxy)cyclohexanone is used as a raw material and is only subjected to reduction and hydrolysis so as to conveniently synthesize cis-1,4-cyclohexanediol. The method can guarantee high selectivity of the reactions, and is high in the yieldof cis-1,4-cyclohexanediol and suitable for large-scale production.
Selective aliphatic carbon-hydrogen bond activation of protected alcohol substrates by cytochrome P450 enzymes
Bell, Stephen G.,Spence, Justin T. J.,Liu, Shenglan,George, Jonathan H.,Wong, Luet-Lok
, p. 2479 - 2488 (2014/04/03)
Protected cyclohexanol and cyclohex-2-enol substrates, containing benzyl ether and benzoate ester moieties, were designed to fit into the active site of the Tyr96Ala mutant of cytochrome P450cam. The protected cyclohexanol substrates were efficiently and selectively hydroxylated by the mutant enzyme at the trans C-H bond of C-4 on the cyclohexyl ring. The selectivity of oxidation of the benzoate ester protected cyclohexanol could be altered by making alternative amino acid substitutions in the P450cam active site. The addition of the double bond in the cyclohexyl ring of the benzoate ester protected cyclohex-2-enol has a debilitative effect on the activity of the Tyr96Ala mutant with this substrate. However, the Phe87Ala/Tyr96Phe double mutant, which introduces space at a different location in the active site than the Tyr96Ala mutant, was able to efficiently hydroxylate the C-H bonds of 1-cyclohex-2-enyl benzoate at the allylic C-4 position. Mutations at Phe87 improved the selectivity of the oxidation of 1-phenyl-1-cyclohexylethylene to trans-4-phenyl-ethenylcyclohexanol (92%) when compared to single mutants at Tyr96 of P450cam. the Partner Organisations 2014.
Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: Entry into the Fischer indole synthesis
Zhan, Fuxu,Liang, Guangxin
supporting information, p. 1266 - 1269 (2013/03/13)
Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine. Copyright
Discovery of bacterial NAD+-dependent DNA ligase inhibitors: Improvements in clearance of adenosine series
Stokes, Suzanne S.,Gowravaram, Madhusudhan,Huynh, Hoan,Lu, Min,Mullen, George B.,Chen, Brendan,Albert, Robert,O'Shea, Thomas J.,Rooney, Michael T.,Hu, Haiqing,Newman, Joseph V.,Mills, Scott D.
scheme or table, p. 85 - 89 (2012/03/10)
Optimization of clearance of adenosine inhibitors of bacterial NAD +-dependent DNA ligase is discussed. To reduce Cytochrome P-450-mediated metabolic clearance, many strategies were explored; however, most modifications resulted in compounds wi
CATALYTIC RADIOFLUORINATION
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Page/Page column 97-98, (2010/11/30)
One aspect of the present invention relates to a method of preparing radio fluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to arylammonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the ammonium compound is a tetraaryl ammonium salt. Another aspect of the invention relates to arylsulfonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the sulfonium compound is a triaryl sulfonium salt. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.
CATALYTIC RADIOFLUORINATION
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Page/Page column 75, (2008/06/13)
One aspect of the present invention relates to a method of preparing radiofluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to piperazine compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the piperazine compounds contain a quaternary amine. Another aspect of the invention relates to arylphosphonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the phosphonium compound is a tetraaryl phosphonium sait. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.
A convenient route for the synthesis of cis-1-substituted 1,2,3,4,4a,5,11,11a-octahydro-6H-pyrido[3,2-b]carbazoles and 4-substituted 1,2,3,4,4a,5,6,11c-octahydro-7H-pyrido[2,3-c] carbazoles as potent dopamine agonists
Awasthi, Keshav K.,Chakrabarty, Ruchika,Saxena, Anil K.
, p. 758 - 769 (2007/10/03)
The cis-1/4 substituted octahydropyrido[(3,2-b)/(2,3-c)]carbazoles have shown potent dopamine agonistic activity in vitro and in vivo. The reported method of their synthesis involves hydrogenation at high temperature and pressure. Some attempts have been
Biohydroxylation reactions catalyzed by enzymes and whole-cell systems
Flitsch, Sabine L.,Aitken, Suzanne J.,Chow, Cathy S.-Y.,Grogan, Gideon,Staines, Adam
, p. 81 - 90 (2007/10/03)
The biohydroxylation of a number of cyclic substrates (3-24) containing aromatic side chains was used to compare substrate specificity and selectivity of hydroxylation using microbial enzymes and whole-cell biocatalysts. In general, the regioselectivity of reaction was remarkably similar between the different catalysts in that little aromatic or benzylic, but significant aliphatic hydroxylation was observed. However, a more detailed investigation of isolated products showed complementary substrate specificity, functional group compatibility, and regioselectivity of hydroxylation. Substrate specificity and regioselectivity could be further modulated by small changes to the nature of the aromatic side chain, which appears to play an important role in substrate recognition.
1,2-Disubstituted Ethanes As Possible Precursors For The Synthesis of Cannabis Spirans
Crombie, Leslie,Crombie, W. Mary L.,Jamieson, Sally V.,Tuchinda Patoomratana,Whitaker, Alison J.
, p. 1485 - 1492 (2007/10/02)
Three possible methods for converting suitable 1,2-disubstituted ethanes into Cannabis spirans have been investigated. 4',5-Dihydroxy-3-methoxybibenzyl underwent intramolecular o-p- and p-p-coupling with ferricyanide in a chloroform-aqueous potassium carbonate system, but yields were low: certain other oxidants did not succeed or gave only traces of product.A method for making 1-hydroxy-1-(3,5-dimethoxyphenylethyl)cyclohexan-4-one ethylene acetal or thioacetal via a Birch reaction is described: despite favourable precedent, acid-catalysed cyclisation led to octahydrophenanthrenones rather than spiro-ketones, whilst N,N-dimethylformamide dineopentyl acetal gave two olefins.Jacquesy's super-asid method for making spirocyclohexenones from a methoxylated bibenzyl was not applicable to the 3,4',5-trimethoxy-case, which would have given cannabispirenone methyl ether, presumably because of protonation of both aromatic systems.
