- Rodlike molecules by Kolbe electrolysis
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A new short and simple pathway to rigid, rod-shaped hydrocarbon skeletons, in particular of the oligo-bicyclo[2.2.2]octane type, is described. The key step consists of an electrochemical C-C bond coupling reaction between bridgehead positions of bi- and tricyclic carboxylic acids. Functional groups can be retained, they influence the yield of the C-C bond connection. In this way, otherwise difficult or laborious syntheses are shortened, and rigid, non-collapsable nano size spacer units are easily available. The optimized electrochemical procedures are described in detail.
- Nuding,V?gtle,Danielmeier,Steckhan
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Read Online
- Design and synthesis of novel 19F-amino acid: A promising 19F NMR label for peptide studies
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Novel aliphatic 19F-substituted amino acid was designed as a 19F NMR label for peptide studies. The synthesis was performed in 11 steps and 9% overall yield from a commercially available starting material. The key transformation was a decarboxylative fluorination of an aliphatic carboxylic acid with XeF2 in C6F6.
- Bandak, Dmytro,Babii, Oleg,Vasiuta, Roman,Komarov, Igor V.,Mykhailiuk, Pavel K.
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Read Online
- Unique gas and hydrocarbon adsorption in a highly porous metal-organic framework made of extended aliphatic ligands
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High and unique gas and hydrocarbon adsorption in a highly stable guest-free microporous metal-organic framework constructed on rigid aliphatic ligands, H2bodc and ted, is reported in this work. The Royal Society of Chemistry.
- Li, Kunhao,Lee, Jeongyong,Olson, David H.,Emge, Thomas J.,Bi, Wenhua,Eibling, Matthew J.,Li, Jing
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Read Online
- SYNTHESIS OF BICYCLO[2.2.2]OCTANE DERIVATIVES
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Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.
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- Bicyclo [2.2.2] octane - 1, 4 - dicarboxylic acid mono methyl ester synthesis method
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The invention relates to a synthetic method of an organic compound. The synthetic method of bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl easter is as follows: firstly, adopting sodium hydride, DMSS and 1,2-dibromoethane to synthesize the intermediate I; secondly, adopting the intermediate I, sodium acetate, ammourea hydrochloride and alcohol to synthesize semicarbazon; thirdly, adopting potassium hydroxide, diethylene glycol and semicarbazon to synthesize target diacid; fourthly, adopting target diacid, thionyl chloride and methanol to synthesize target diester; and fifthly, adopting target diester, potassium hydroxide and 95% of methanol water solution to synthesize the target product monoester. The invention has reasonable synthetic process route, mild process conditions, environment friendly, easy operation, low raw material cost, high product yield and excellent purity, and is applicable to industrial production and satisfies the application requirement of each industry.
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- Tuning Singlet Fission in π-Bridge-π Chromophores
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We have designed a series of pentacene dimers separated by homoconjugated or nonconjugated bridges that exhibit fast and efficient intramolecular singlet exciton fission (iSF). These materials are distinctive among reported iSF compounds because they exist in the unexplored regime of close spatial proximity but weak electronic coupling between the singlet exciton and triplet pair states. Using transient absorption spectroscopy to investigate photophysics in these molecules, we find that homoconjugated dimers display desirable excited-state dynamics, with significantly reduced recombination rates as compared to conjugated dimers with similar singlet fission rates. In addition, unlike conjugated dimers, the time constants for singlet fission are relatively insensitive to the interplanar angle between chromophores, since rotation about σ bonds negligibly affects the orbital overlap within the π-bonding network. In the nonconjugated dimer, where the iSF occurs with a time constant >10 ns, comparable to the fluorescence lifetime, we used electron spin resonance spectroscopy to unequivocally establish the formation of triplet-triplet multiexcitons and uncoupled triplet excitons through singlet fission. Together, these studies enable us to articulate the role of the conjugation motif in iSF.
- Kumarasamy, Elango,Sanders, Samuel N.,Tayebjee, Murad J. Y.,Asadpoordarvish, Amir,Hele, Timothy J. H.,Fuemmeler, Eric G.,Pun, Andrew B.,Yablon, Lauren M.,Low, Jonathan Z.,Paley, Daniel W.,Dean, Jacob C.,Choi, Bonnie,Scholes, Gregory D.,Steigerwald, Michael L.,Ananth, Nandini,McCamey, Dane R.,Sfeir, Matthew Y.,Campos, Luis M.
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supporting information
p. 12488 - 12494
(2017/09/23)
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- SPIRO AZETIDINE ISOXAZOLE DERIVATIVES AND THEIR USE AS SSTR5 ANTAGONISTS
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Provided is a compound represented by the following formula (1) or a salt thereof, which has an SSTR5 antagonistic action: wherein each symbol has the same definition as in the specification.
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Paragraph 1286
(2014/09/29)
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- Discovery of functionalized bisimidazoles bearing cyclic aliphatic-phenyl motifs as HCV NS5A inhibitors
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This Letter describes the discovery of a number of functionalized bisimidazoles bearing a cyclohexylphenyl, piperidylphenyl, or bicyclo[2,2,2]octylphenyl motif as HCV NS5A inhibitors. Compounds 2c, 4b and 6 have demonstrated low single-digit nM potency in gt-1a replicon and double-digit pM potency in gt-1b replicon, respectively. Moreover, both 4b and 6 have, respectively, exhibited good oral bioavailability in rats with a favorable liver/plasma ratio of the drug concentration.
- Zhong, Min,Peng, Eric,Huang, Ningwu,Huang, Qi,Huq, Anja,Lau, Meiyen,Colonno, Richard,Li, Leping
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p. 5731 - 5737
(2015/01/08)
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- BRIDGED BICYCLIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Novel bridged bicyclic compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.
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Page/Page column 64
(2013/03/26)
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- SUBSTITUTED DIAMINOCARBOXAMIDE AND DIAMINOCARBONITRILE PYRIMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
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Provided herein are Diaminopyrimidine Compounds having the following structures: wherein R1, R2, R3, and R4 are as defined herein, compositions comprising an effective amount of a Diaminopyrimidine Compound, and methods for treating or preventing liver fibrotic disorders or a condition treatable or preventable by inhibition of a JNK pathway.
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Page/Page column 134; 135
(2012/11/07)
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- NOVEL AMIDE AND AMIDINE DERIVATIVES AND USES THEREOF
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The present invention relates to inhibitors of 11-β-hydroxysteroid dehydrogenase type 1 enzyme and their use in treatment of non-insulin dependent type 2 diabetes, insulin resistance, obesity, lipid disorders, metabolic syndrome, central nervous system disorders, and diseases and conditions that are related to excessive glucocorticoids.
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Page/Page column 31-32
(2010/11/03)
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- HETEROBICYCLIC METALLOPROTEASE INHIBITORS
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The present invention relates generally to heterobicyclic containing pharmaceutical agents, and in particular, to heterobicyclic metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of heterobicyclic metalloprotease inhibiting compounds that exhibit an increased potency in relation to currently known metalloprotease inhibitors.
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Page/Page column 177
(2008/12/05)
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- Convenient one-pot preparation of dimethyl bicyclo[2.2.2]octane-1,4- dicarbolylate, a key intermediate for a novel adenosine A1 receptor antagonist
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Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (4), a key starting material for a novel adenosine A1 receptor antagonist, was prepared in a one-pot reaction with convenient workup and improved yield. Copyright Taylor & Francis Group, LLC.
- Chang, HeXi,Kiesman, William F.,Petter, Russell C.
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p. 1267 - 1272
(2008/02/01)
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- HETEROBICYCLIC METALLOPROTEASE INHIBITORS
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The present invention relates generally to amide group containing pharmaceutical agents, and in particular, to amide containing heterobicyclic metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of heterobicyclic MMP- 13 inhibiting compounds, that exhibit an increased potency in relation to currently known MMP- 13 inhibitors.
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Page/Page column 164-165
(2008/06/13)
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- PEPTIDASE INHIBITORS
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The present invention relates to a series of novel compounds having the formula: [INSERT FORMULA I] wherein A is a bicyclic carbocycle and R?1? and R?2? are independently [INSERT MOLECULE FROM CLAIM 1] The compounds are useful as DPP-IV inhibitors and for treating diabetes.
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Page/Page column 32-33
(2010/10/19)
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- Adenosine receptor antagonists and methods of making and using the same
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The invention is based on the discovery that compounds of Formula I are unexpectedly highly potent and selective inhibitors of the adenosine A1receptor. Adenosine A1antagonists can be usefull in the prevention and/or treatment of numerous diseases, including cardiac and circulatory disorders, degenerative disorders of the central nervous system, respiratory disorders, and many diseases for which diuretic treatment is suitable. In one embodiment, the invention features a compound of formula I: wherein: R3is an optionally substituted bicyclic, tricylic, or pentacyclic group selected from: ?and wherein R1, R2, R6, X1, X2, and Z are as described in the specification.
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Page/Page column 51-52
(2008/06/13)
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- The synthesis of [2.2.2]bicyclooctane and [3.1.1]bicycloheptane based amino acids as constrained glutamate analogues
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A novel [2.2.2]bicyclooctane analogue of glutamic acid was synthesised using a modification of the Corey-Link amino acid synthesis. A related [3.1.1]bicycloheptane was prepared by cyclising a symmetrical 4,4- disubstituted cyclohexanone.
- Richard Baker,Hancox, Timothy C.
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p. 781 - 784
(2007/10/03)
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- HYDROGENOLYSIS OF CUBANE
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On catalytic hydrogenation over Pd-C under normal conditions cubane (10) takes up 3 mol of hydrogen in a few hours.Bicyclooctane (13) is formed as the main product, and tetracyclo2.5.03.8>octane (11, secocubane) and tricyclo2.5>octane (12, nortwistbrendane) have been identified as intermediates.The hydrogenolysis of dimethyl 1,4-cubane dicarboxylate, as well as cuneane derivatives, have also been studied.Results are discussed in terms of strain relief calculated by the molecular mechanics method for cubane-like structures.
- Stober, Reinhard,Musso, Hans,Osawa, Eiji
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p. 1757 - 1762
(2007/10/02)
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- Synthesis of Bridgehead-Bridgehead Substituted Bicycloalkanes
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A convenient synthetic route to several bicycloalkanes bearing substitution at both bridgehead positions is described.The two-step procedure, which involves alkylation of the monoenolates of readily available cyclohexane diesters with 1,2-dihaloethane followed by a base-inducted cyclization of the derived haloethylated product, was successfully applied to the synthesis of dimethyl bicyclooctane-1,4-dicarboxylate, dimethyl bicycloheptane-1,4-dicarboxylate and dimethyl bicyclooctane-1,5-dicarboxylate.Additionally, it was found that the two latter diesters could be obtained in quite acceptable yields in a one-pot procedure through their corresponding cyclohexyl bisenolate precursors.
- Della, Ernest W.,Tsanaktsidis, John
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p. 1705 - 1718
(2007/10/02)
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