- Synthesis of a novel series of topographically constrained amino acids: Benzo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids
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A novel series of benzo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids (benzo-Tic), designed by extending the aromatic system of Tic (Tic=1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) in three different orientation, has been synthesized.
- Wang, Chenguang,Mosberg, Henry I.
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- Synthesis of Benzo-Fused Tetraphenylenes and Crystal Structure of a 4:1 Clathrate Inclusion Compound of Dibenzotetraphenylene with p-Xylene
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Benzo-fused tetraphenylenes 2-6 were successfully prepared by the combined deployment of the Diels-Alder cycloaddition between some strained cyclooctynes and furans and subsequent low-valent-titanium deoxygenation of the resulting 1,4-endoxides.As expecte
- Man, Yuet-Ming,Mak, Thomas C. W.,Wong, Henry N. C.
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- Effects of solubilizing group modification in fullerene bis-adducts on normal and inverted type polymer solar cells
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Structural control of solubilizing side groups in fullerene-based electron acceptors is critically important to optimize their performance in bulk heterojunction (BHJ)-type polymer solar cell (PSC) devices. The structural changes of fullerene derivatives
- Kim, Ki-Hyun,Kang, Hyunbum,Kim, Hyeong Jun,Kim, Pan Seok,Yoon, Sung Cheol,Kim, Bumjoon J.
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- An alternative approach: A highly selective dual responding fluoride sensor having active methylene group as binding site
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A newly designed phosphonium derivative (L) having active methylene functionality, shows unusual preference towards F- over all other anions. The binding process through C-H...F- hydrogen bond formation was probed by monitoring the c
- Das, Priyadip,Kesharwani, Manoj K.,Mandal, Amal K.,Suresh, Eringathodi,Ganguly, Bishwajit,Das, Amitava
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- Understanding the binding properties of phosphorylated glycoluril-derived molecular tweezers and selective nanomolar binding of natural polyamines in aqueous solution
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A modular synthetic platform for the construction of flexible glycoluril-derived molecular tweezers was developed. The binding properties of four exemplary supramolecular hosts obtained via this approach towards 16 organic amines were investigated by means of 1H NMR titration. In this work, we compare the Ka values obtained this way with those of three structurally related molecular tweezers and provide a computational approach towards an explanation of the observed behavior of those novel hosts. The results showcase that certain structural modifications lead to very potent and selective binders of natural polyamines, with observed binding of spermine below 10 nM. This journal is
- Heilmann, Michael,Knezevic, Melina,Piccini, Giovannimaria,Tiefenbacher, Konrad
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supporting information
p. 3628 - 3633
(2021/05/04)
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- Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde
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The Diels-Alder reaction, which is a traditional [4 + 2] cycloaddition with two carbon-carbon bond formations, is one of the most powerful tools to synthesize versatile and unique six-membered rings. We show that chiral supramolecular U-shaped boron Lewis acid catalysts promote the unprecedented multiselective Diels-Alder reaction of propargyl aldehyde with cyclic dienes. Independent from the substrate control, enantio-, endo/exo-, π-facial-, regio-, site-, and substrate-selectivities could be controlled by the present U-shaped catalysts. The obtained reaction products could access the concise synthesis of chiral diene ligands and a key intermediate of (+)-sarkomycin. The results presented here might partially contribute to the development of artificial enzyme-like supramolecular catalysts for multiselective reactions, which will be able to target organic compounds that have thus far eluded synthesis.
- Hatano, Manabu,Sakamoto, Tatsuhiro,Mizuno, Tomokazu,Goto, Yuta,Ishihara, Kazuaki
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supporting information
p. 16253 - 16263
(2018/11/27)
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- Cationic Tags for Attomole Level Detection of Analytes by Mass Spectrometry
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The invention provides methods of detecting an analyte by multi-stage mass spectrometry with improved S/N ratio. An analyte is labeled with a positively-charged mass tag to form a precursor ion that leads by anchimeric assistance to a greatly enhanced, analyte-characteristic first product ion that can, in turn, lead to a greatly enhanced, analyte-characteristic second product ion in a mass spectrometer. Either a three stage mass spectrometer (true MS3) or a two-stage mass spectrometer (MS2) operated in a pseudo MS3 mode can be used. The precursor ion is split via an anchimeric-assisted reaction to form a first product ion, which in turn can be fragmented to form the second product ion. The methods offer extreme ultrasensitivity, at the low amol level. The invention also provides anchimeric mass tags for use in the methods. A wide variety of previously undetectable analytes of biological or environmental origin can be detected and quantified.
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Paragraph 0080
(2018/02/28)
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- Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes
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Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.
- Xu, Feng,Peng, Lifen,Shinohara, Kenta,Morita, Takamoto,Yoshida, Suguru,Hosoya, Takamitsu,Orita, Akihiro,Otera, Junzo
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p. 11592 - 11608
(2015/01/09)
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- Fullerene Derivatives and Organic Electronic Device Comprising the Same
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The present invention relates to fullerene derivatives and an organic electronic device using the same, and more specifically, to a novel fullerene derivative incorporating an aromatic fused ring compound and to an organic electronic device with excellent
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Page/Page column 10
(2012/01/14)
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- FULLERENE DERIVATIVES AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME
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The present invention relates to fullerene derivatives and an organic electronic device using the same, and more specifically, to a novel fullerene derivative incorporating an aromatic fused ring compound and to an organic electronic device with excellent
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Page/Page column 17
(2011/12/14)
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- Naphtho- and benzo[g]quinoxalino-fused oxazocinoquinolinones and their diaryl and alkynyl analogues from quinolin-8-ols: A library of novel polynuclear heteroaromatics
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The efficient syntheses of 6,6,8,6,6-pentacyclic naphtho-fused oxazocinoquinolinones and 6,6,8,6,6,6-hexacyclic benzo[g]quinoxalino-fused oxazocinoquinolinones were achieved in one-pot sequences. The generation of libraries of their diaryl- and alkynyl-su
- Mondal, Nirup B.,Paira, Rupankar,Maity, Arindam,Naskar, Subhendu,Mondal, Shyamal,Paira, Priyankar,Hazra, Abhijit,Sahu, Krishnendu B.,Saha, Pritam,Banerjee, Sukdeb
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scheme or table
p. 3520 - 3535
(2010/11/19)
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- Secondary interactions in crystals of all ten isomers of Di(bromomethyl)naphthalene
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The packing of all ten isomers of di(bromomethyl)naphthalene is analysed; nine of the structures were determined here, one (the 1,8-isomer) was already known. The 1,5- and 2,6-isomers display crystallographic inversion symmetry and the 2,7-isomer mirror symmetry through the central bond. For the 1,2-, 1,7- and 2,7-isomers, the bromomethyl groups point to the same side of the ring system, and for all other isomers to opposite sides. As expected, the molecules are linked into aggregates by various types of interactions: weak hydrogen bonds CH...Br, Br...Br interactions, CH...π contacts, π ...π stacking and Br...π contacts. The weak hydrogen bonds tend to be numerous but relativelyi; long, and do not combine to form readily recognisable patterns; a more readily assimilated view of the packing is based on the Br...Br interactions, which are observed for all isomers except 1,7 and 2,3, and in some cases lead to aggregation to form quadrilaterals or chains. With decreasing frequency, the interactions π ...π, C-H...π and Br...π are observed, but the latter are rare (just two examples) and very asymmetric, with contacts to only one or two carbons.
- Jones, Peter G.,Kus, Piotr
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experimental part
p. 433 - 444
(2010/10/01)
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- Unique behavior of 2,6-bis(bromomethyl)naphthalene as a highly active organic DNA crosslinking molecule
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Among 14 bis-halomethylated naphthalenes and quinolines, 2,6-bis(bromomethyl)naphthalene was found to have highly active crosslinking activity on DNA. The unique behavior of high microbial mutagenicity, even though it had a low propensity to form double-strands in linearized plasmid DNA, suggested that it would offer a new seed, capable of forming intrastrand crosslinks similar to cisplatin. The electron withdrawal extent of the halogen atoms, the substitution patterns of two halomethyl groups, and the introduction of a nitrogen atom into the aromatic nucleus had remarkable effects on the activity of the molecule.
- Higashi, Toshinori,Uemura, Koichi,Inami, Keiko,Mochizuki, Masataka
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supporting information; experimental part
p. 3568 - 3571
(2009/09/27)
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- Indanyl-piperazine compounds
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A compound selected from those of formula (I): wherein: R3 represents a hydrogen atom, and R1 and R2 together with the carbon atoms carrying them form a benzene, naphthalene or quinoline ring structure, each of the ring structures being optionally substituted, ?or R1 represents a hydrogen atom, and R2 and R3 together with the carbon atoms carrying them form a benzene, naphthalene or quinoline ring structure, each of the ring structures being optionally substituted, n represents 1 or 2, —X— represents a group selected from —(CH2)m—O-Ak-, —(CH2)m—NR4-Ak-, —(CO)—NR4-Ak- and —(CH2)m—NR4-(CO)—, ?m represents an integer between 1 and 6 inclusive, Ak represents an optionally substituted alkylene chain, and R4 represents a hydrogen atom or an alkyl group, Ar represents an aryl or heteroaryl group, its enantiomers, diasteroisomers, and addition salts thereof with a pharmaceutically acceptable acid. Medical products containing the same which are useful in the treatment of conditions requiring a serotonin reuptake inhibitor and/or NK1 antagonist.
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(2010/11/24)
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- Synthesis of the first tetracene-[60]fullerene dyad
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We report on a multistep synthesis of the newly designed tetracene-[60]fullerene dyad involing a Bingel reaction between the tetracene and C60 moieties. This strategy prevents the usual Diels-Alder reaction which would result in the loss of the
- Taillemite, Sebastien,Fichou, Denis
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p. 4981 - 4984
(2007/10/03)
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- Highly enantioselective and practical cinchona-derived phase-transfer catalysts for the synthesis of α-amino acids
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A new class of naphthalene-based dimeric cinchona alkaloids 1 are very efficient and practical phase-transfer catalysts in the alkylation of a glycine derivative. The mild reaction conditions and the high catalytic efficiency (high yields and ee values) could make these alkaloids practical catalysts in the industrial synthetic process for natural and nonnatural chiral α-amino acids.
- Park, Hyeung-Geun,Jeong, Byeong-Seon,Yoo, Mi-Sook,Lee, Jeong-Hee,Park, Mi-Kyoung,Lee, Yeon-Ju,Kim, Mi-Jeong,Jew, Sang-Sup
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p. 3036 - 3038
(2007/10/03)
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- The synthesis of naphthosultine and benzodisultines and their pyrolysis with dienophiles: Studies on o-naphthoquinodimethane and bis-o-quinodimethane
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Sealed tube reactions of the naphthosultine 8 with a series of electron-deficient dienophiles (fumaronitrile, N-phenylmaleimide, dimethyl fumarate, and dimethyl acetylenedicarboxylate) in toluene at 180 °C gave corresponding 1:1 cycloadducts 11-14 in various amounts along with rearranged naphthosulfolene 7 in 67-95% yields. The reaction of 1,2,4,5-tetra(bromomethyl) benzene with Rongalite (sodium formaldehyde sulfoxylate) and tetrabuty lammonium bromide in DMF gave benzodisultines 17 and 18 in a combined yield of 56%. Sealed tube reactions of benzodisultines 17 and 18 with a series of dienophiles in xylene at 200 °C gave corresponding 1:1 and 1:2 cycloadducts 20-27. The results suggested that thermal extrusion of sulfur dioxide from these sultines led to either o-naphthoquinodimethane 6 (from 8) or bis-o-quinodimethane 19 (from 17 and 18); subsequent trapping of these reactive intermediates by dienophiles and SO2 gave various 1:1 and 1:2 Diels-Alder adducts in modest to excellent yields.
- Wu, An-Tai,Liu, Wen-Dar,Chung, Wen-Sheng
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- 7-Spiroindanyl derivatives of naltrexone and oxymorphone as selective ligands for δ opioid receptors
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A series consisting of spiroindanyl (5-7), benzospiroindanyl (8-10), and spiroperinaphthyl (11) derivatives of naltrexone and oxymorphone were synthesized in order to investigate the role of an orthogonal-oriented 'address' for δ opioid receptors. All of
- Ohkawa,DiGiacomo,Larson,Takemori,Portoghese
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p. 1720 - 1725
(2007/10/03)
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- New heteroaryl-spaced phosphono α-amino acids are competitive NMDA antagonists with analgesic activity
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The synthesis and the NMDA receptor binding affinities of α-amino-3-(phosphonomethyl)-2-naphthalenepropanoic acid, α-amino-3-(phosphonomethyl)-2-benzofuranpropanoic acid, a series of substituted (R)-α-amino-3-(phosphonomethyl)-2-quinolinepropanoic acids, (R)-α-amino-3-(phosphonomethyl)-1,8-naphthyridine-2-propanoic acid and (R)-α-amino-3-(phosphonomethyl)-1,6-naphthyridine-2-propanoic acid are reported.
- Swahn, Britt-Marie,Claesson, Alf,Pelcman, Benjamin,Besidski, Yevgeni,Molin, Hakan,Sandberg, Mats P.,Berge, Odd-Geir
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p. 1635 - 1640
(2007/10/03)
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- Phosphonic acid derivatives useful as anti-inflammatory agents
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Novel 1,2-oxaphosphepins are useful as antiinflammatory and antiarthritic agents. A representative oxaphosphepin is 3,4-dihydro-3-methoxy-7-(phenylmethoxy)-1H-naphth[1,8de][1,2]oxaphosphepin-3-oxide.
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- Phosphonic acid derivatives useful as anti-inflammatory agents
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Novel acids, esters, and salts of phenyl, naphthyl, quinoxalinyl, and biphenyl bisphosphonic acids and 1,2-oxaphosphepins are described. These compounds are useful as antiinflammatory and anti-arthritic agents. Also described are known compounds of the phenyl, naphthyl, quinoxalinyl, and biphenyl bisphosphonate classes which are also useful as antiinflammatory and anti-arthritic agents. Representative compounds include [1,2-phenyldiyl]bis (methylene)bisphosphonic acid tetramethyl ester, [2,3-quinoxalindiyl]bis(methylene)bisphosphonic acid tetramethyl ester, [[3-(propyl)-4-(methoxy)-1,8-naphthalenediyl]bis(methylene)]bisphosphonic acid tetramethyl ester, [2,6-naphthalenediylbis(methylene) bisphosphonic acid tetraethyl ester, and [2,2'-biphenylenebis(methyl)]bisphosphonic acid tetramethyl ester. Representative oxaphosphepins include the preferred 3,4-dihydro-3-methoxy -7-(phenylmethoxy)-1H-naphth[1,8de][1,2]oxaphosphepin-3-oxide.
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- Principal Component-Three Component Self-Modeling Analysis Applied to trans-1,2-Di(2-naphthyl)ethene Fluorescence
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Fluorescence spectra of trans-1,2-di(2-naphthyl)ethene, DNE, obtained under varying conditions of excitation wavelength and oxygen and carbon tetrachloride concentrations in methylcyclohexane were resolved into three distinct components by application of principal component analysis combined with a three-component self-modeling technique.Spectral matrices for O2 and CCl4 quenching, treated separately, yielded nearly identical pure component fluorescence spectra.The spectra were assigned to each of the three conformers of DNE by comparison with spectra of 3-methyl derivatives.Stern-Volmer quenching plots for the individual conformers were shown to be independent of excitation wavelength, indicating that each conformer has a single lifetime.
- Sun, Ya-Ping,Sears, Donald F.,Saltiel, Jack,Mallory, Frank B.,Mallory, Clelia W.,Buser, Carolyn A.
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p. 6974 - 6984
(2007/10/02)
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- 1H NMR Study of Two Tetrahydrocyclodecabiphenylenes
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5,6,9,10-Tetradehydrobenzocyclodecabiphenylene (2) and 5,6,9,10-tetrahydronaphthocyclodecabiphenylene (3) were prepared by a "bis-Wittig reaction between 1,8-bis((triphenylphosphoranylidene)methyl)biphenylene (5) an
- Wilcox, Charles F,,Weber, Karl A.
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p. 1088 - 1094
(2007/10/02)
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- Synthesis of Crown Ethers That Geometrically Orient Cations Relative to a Naphthalene ? System. A Look at the Equilibration of Enantiomeric Conformations by "Rope-Skipping" Crown Ethers
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A number of new naphthalene crown ethers were synthesized in moderate yield from the appropriate bis(halomethyl)naphthalenes and polyethylene glycols.The following crown ethers were synthesized: 2,3-naphtho-14-crown-4 (15percent), 2,3-naphtho-17-crown-5 (19percent), 2,3-naphtho-20-crown-6 (36percent), 1,8-naphtho-15-crown-4 (20percent), 1,8-naphtho-18-crown-5 (7percent), 1,8-naphtho-21-crown-6 (38percent), 1,2-naphtho-20-crown-6 (4percent), 1,5-naphtho-22-crown-6 (14percent), 1,5-naphtho-19-crown-5 (11percent), 1,4-naphtho-22-crown-6 (9percent), 1,3-naphtho-21-crown-6 (16percent).These crown compounds form a series in which complexed cations perturb the naphthalene ? system from different directions.Experimental evidence concerning the ease of equilibration of enantiomeric conformations by "rope-skipping" crown ethers is also reported.The equilibration of 1,5-naphtho-22-crown-6 enantiomeric conformations has about a 6.3-kcal energy of activation, while the corresponding barrier for 1,5-naphtho-19-crown-5 is greater than 21 kcal.
- Brown, Houston S.,Muenchausen, Chrysa P.,Sousa, Lynn R.
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p. 1682 - 1686
(2007/10/02)
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- Synthesis of Potentially Basic Hydrocarbons by Sulphur Extrusion and/or Bis-Wittig Reactions. Two Syntheses of Benzindenophenalene and a New Synthesis of Dibenzonaphthacene (Zethrene)
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Macrocyclic bis-sulphides have been prepared from 1,2-, 2,3-, and 1,8-bis(bromomethyl)naphthalenes.Methylation of the bis-sulphides, followed by the Stevens rearrangement, gave the corresponding carbocycles with extra-annular sulphide groups; removal of these sulphide groups by Hofmann elimination led to spontaneous trans-annular condensation.Using this general method, two hydrocarbons were synthesized: benzindenophenalene and dibenzonaphthacene (or zethrene).An alternative synthetic route led to the synthesis of benzindenophenalene, using the Wittig reaction between naphthalene-2,3-carbaldehyde and 1,8-bis(triphenylphosphoniomethyl)naphthalene dibromide.
- Kemp, William,Storie, Iain T.,Tulloch, Charles D.
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p. 2812 - 2817
(2007/10/02)
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