30680-84-3Relevant academic research and scientific papers
Conformationally Defined Analogs of Prolylamides. trans-Prolyl Peptidomimetics
Andres, Charles J.,Macdonald, Timothy L.,Ocain, Timothy D.,Longhi, Daniel
, p. 6609 - 6613 (1993)
The cis and trans conformations of prolylamides are both energetically accessible, in contrast to the peptide bonds of the remaining mammalian amino acids.The synthesis of a rigid, conformationally defined peptidomimetic of the trans-prolylamide bond has been developed in this study, and illustrative leucinylproline derivatives (4, 10a, 10b, and 11) were assayed for their abilities to inhibit the peptidyl prolyl isomerase activity of recombinant human FK-binding protein 12 (FKBP 12).These trans-prolyl peptidomimetics possess a trans-substituted alkene in place of the proline peptide bond and were synthesized via a six step sequence culminating in the selective addition of isobutylmagnesium bromide to 2(E)-(2-oxoethylidene)-1-methylcyclopentanecarboxylate (9).Synthesis of the dipeptide analogs was accomplished in six steps with a 20percent overall yield.Elaboeation of the dipeptide analog gave the Leu-Pro-tyrosyl tripeptide analog in three additional steps.The tripeptide mimic 4 proved to be a potent inhibitor of the prolyl isomerase activity of recombinant hFKBP 12, exhibiting an inhibition constant (Ki) of 8.6 μM; the dipeptidomimetics possessed a modest capacity for isomerase inhibition with inhibition constants ranging from 127 μM for the α-enone analog 11 to 730 and 1390 μM for the allylic alcohol mimetics 10a and 10b, respectively.
Preparation method of 2, 2-dimethyl cyclopentanone
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Paragraph 0017, (2021/06/23)
The invention discloses a preparation method of 2, 2-dimethyl cyclopentanone, which comprises the following steps: methylating 2-methoxycarbonyl cyclopentanone to obtain a methylated product 2-methyl-2-methoxycarbonyl cyclopentanone, carrying out keto-carbonyl protection on the methylated product to obtain a protected product 2-methyl-2-methoxycarbonyl cyclopentanone ketal, carrying out ester group reduction on the protection product to obtain an alcohol product 2-hydroxymethyl-2-methyl cyclopentanone ketal, carrying out deprotection on the alcohol product under an acidic condition to obtain a deprotection product 2-hydroxymethyl-2-methyl cyclopentanone, and brominating the deprotection product to obtain 2-bromomethyl-2-methyl cyclopentanone. All raw materials adopted by the method are low in cost and easy to obtain in the market, and reactions in all steps are conventional reactions and easy to implement; the process is simple, mild in reaction condition and easy to operate; the reaction time is short, control is easy, the yield of each step is 90% or above, and industrial large-scale production is easy to achieve.
Preparation method of metconazole (by machine translation)
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Paragraph 0052-0054, (2019/10/01)
The method comprises the following steps: 2 - (2 - chlorobenzylidene) 2 - 2 -methylcyclopentanone and p-chlorobenzaldehyde react to obtain an epoxide; the epoxide reacts with triazole to obtain an epoxide; and the epoxide is reacted with triazole to obtain an open-loop product; and the ring-opening product 4 - is subjected -2 to 2 - catalytic hydrogenation to obtain the 2 - myclobutanil . 4 - beta-(4 -chlorbenzydrospirone; 5 -2 -5 -chlorobenzyl) 5 - and methylcyclopentanone react. Corey-Chayyyysky is obtained. The preparation method is low in cost, easy to obtain in the market; the reaction steps are all conventional reactions, reaction steps are simple, implementation; process is simple, reaction conditions are mild, operation; conversion rate is high, reaction time is short, control, and industrialization production. (by machine translation)
SULFONYLCYCLOALKYL CARBOXAMIDE COMPOUNDS AS TRPA1 MODULATORS
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Paragraph 0165; 0278; 0279; 0280; 0281; 0282, (2018/02/28)
The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.
Catalytic asymmetric intramolecular homologation of ketones with α-diazoesters: Synthesis of cyclic α-Aryl/Alkyl β-ketoesters
Li, Wei,Tan, Fei,Hao, Xiaoyu,Wang, Gang,Tang, Yu,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 1608 - 1611 (2015/01/30)
A catalytic asymmetric intramolecular homologation of simple ketones with α-diazoesters was firstly accomplished with a chiral N,N′-dioxide-Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α-aryl/alkyl β-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl- and alkyl-substituted ketone groups reacted with α-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β-ketoesters in high yield and enantiomeric excess.
Chemo-, regio-, and stereo-selective perfluoroalkylations by a Grignard complex with zirconocene
Fujiu, Motohiro,Negishi, Kazuyuki,Guang, Jie,Williard, Paul G.,Kuroki, Shigeki,Mikami, Koichi
supporting information, p. 19464 - 19468 (2015/11/27)
The synthesis of highly reactive perfluoroalkyl Grignard reagents with early transition metal zirconocene complexes and their new types of highly chemo-, regio-, and stereo-selective perfluoroalkylation reactions are reported with epoxides in particular. The zirconocene complex is advantageous in activating the perfluoroalkyl Grignard species. The zirconocene·Grignard complexes were clarified by DOSY. Both 1H and 19F DOSY analyses show that the addition of MAO and dioxane to the mixture of RFMgCl and Cp2ZrCl2 connects Cp2Zr and RFMg to generate the zirconocene/perfluoroalkyl-Grignard/dioxane complex.
Electrochemical reduction of 1-bromomethyl-2-oxocycloalkane-1-carboxylates at silver cathodes in dimethylformamide: One-carbon ring-expansion reactions
Wappes, Ethan A.,Mubarak, Mohammad S.,Peters, Dennis G.
, p. G122 - G127 (2015/04/14)
Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the separate electrochemical reductions of methyl 1-bromomethyl-2-oxocyclopentane-1-carboxylate (1) and ethyl 1-bromomethyl-2-oxocyclohexane-1-carboxylate (2) at silver cathodes in dimethylformamide (DMF) containing 0.10 M tetramethylammonium tetrafluoroborate (TMABF4). Oneelectron reductive cleavage of the carbon-bromine bond of each substrate yields a radical intermediate that undergoes a ring-expansion reaction, followed by hydrogen-atom abstraction from the solvent, to afford methyl 3-oxocyclohexane-1-carboxylate (3a) and ethyl 3-oxocycloheptane-1-carboxylate (3b), respectively, in good yield. Each substrate gives rise to three other products: (a) a debrominated analogue of each starting material, (b) a dimeric species formed via radical coupling, and (c) a species possessing an ester group extended by one carbon atom. Electrolyses of 1 and 2 done in the presence of D2O have revealed that carbanion intermediates result in small amounts from two-electron cleavage of carbon-bromine bonds. A mechanistic scheme, involving both radicals and carbanions, is proposed to account for the formation of the various products.
A short formal total synthesis of (±)-hirsutic acid
Revol, Guillaume,Fuchs, Christian,Zard, Samir Z.
, p. 927 - 931 (2013/02/22)
A short formal total synthesis of (±)-hirsutic acid is described using a Claisen rearrangement and a radical cascade as the key steps. The radical sequence involves an intermolecular addition of a radical derived from a xanthate followed by a cyclization and transfer of the xanthate group.
A systematic study of the solid state and solution phase conformational preferences of β-peptides derived from C(3)-alkyl substituted transpentacin derivatives
Abraham, Elin,Claridge, Timothy D.W.,Davies, Stephen G.,Odell, Barbara,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Smith, Lorna J.,Storr, Helen R.,Sweet, Miles J.,Thompson, Amber L.,Thomson, James E.,Tranter, George E.,Watkin, David J.
experimental part, p. 69 - 100 (2011/04/18)
The solid state and solution phase conformational preferences of a homologous series of β-peptides derived from a range of 2-amino-3-alkylcyclopentanecarboxylic acid residues have been investigated using a variety of spectroscopic and crystallographic techniques. These studies indicate that C(3)-alkyl substitution trans to the amino group on the cyclopentane backbone is tolerated by the established 12-helix secondary structural preference of the parent pentamer and hexamer derived from 2-aminocyclopentanecarboxylic acid (transpentacin) residues in both the solid state and solution phase. Evidence for the alternative turn type conformation identified for the C(3)-unsubstituted tetramer was not observed in the C(3)-alkyl substituted derivatives, consistent with the alkyl substituent anti to the amino functionality destabilising this motif. These results suggest that oligomers based around the transpentacin scaffold may be amenable to further elaboration at C(3) anti to the amino group with retention of the secondary structure.
Dynamic chirality of (E)-5-cyclononen-1-one and its enolate
Tomooka, Katsuhiko,Ezawa, Takayuki,Inoue, Hiroko,Uehara, Kazuhiro,Igawa, Kazunobu
supporting information; scheme or table, p. 1754 - 1756 (2011/04/15)
It has been found that (E)-5-cyclononen-1-one (2a) exhibits marginal planar chirality owing to an insufficient topological constraint, whereas the enolates 3 derived from 2a show robust planar chirality. Enantioenriched enolates are easily prepared by enzymatic hydrolysis, and they show an ability to serve as chiral nucleophiles.
