13577-19-0Relevant academic research and scientific papers
Synthesis and photophysical properties of a porphyrin-perinaphthothioindigo dye
Ogawa, Kazuya,Dy, Joanne,Maeda, Rena,Nagatsuka, Yasunori,Kamada, Kenji,Kobuke, Yoshiaki
, p. 821 - 830 (2013)
A new porphyrin-perinaphthothioindigo composite, where porphyrin and perinaphthothioindigo dye are connected though a triple bond, was synthesized. In UV-vis absorption spectra of the composite, absorption originating from the trans-isomer appeared at 655
Weak attractive interactions between methylthio groups and electron-deficient alkenes in peri-naphthalenes: A competition with conjugative effects
O'Leary, Jane,Wallis, John D.
, p. 7724 - 7732 (2006)
The solid-state conformations of five peri-disubstituted naphthalenes bearing a methylthio group and an electron-deficient alkene indicate a weak attractive interaction between the functional groups in four cases in which out-of-plane displacements lead to a common orientation of the MeS...sp2-C vector to the alkene bond. In some cases the interaction is not strong enough to outweigh the tenden cy of the alkene to conjugate with the aromatic ring, and in one case this optimisation of conjugation alone controls the molecular conformation. The methylthio group lies close to the aromatic plane in all but one example for which the plane of the sulfide group is presented to the alkene.
Iodosonaphthoate catalysts for the cleavage of a reactive phosphate
Moss, Robert A.,Zhang, Hongmei,Chatterjee, Swati,Krogh-Jespersen, Karsten
, p. 1729 - 1732 (1993)
Iodosonaphthoates 3-5 are potent catalysts for the hydrolysis of P-nitro-phenyldiphenyl phosphate.
Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents
Wiley, Jenny L.,Smith, Valerie J.,Chen, Jianhong,Martin, Billy R.,Huffman, John W.
experimental part, p. 2067 - 2081 (2012/06/01)
To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl)indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl)indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity.
Porphyrin compound, process for producing porphyrin compound, three-dimensional optical recording material, and three-dimensional optical recording medium
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Page/Page column 25, (2010/11/28)
Compounds that are suitable to be used for three-dimensional optical recording materials, etc. The compounds each have a structure that allows pi-electron conjugation to be achieved by linking a porphyrin ring and a perinaphthothioindigo ring to each other with a straight-chain atomic group. The compounds of the present invention are suitable to be used for three-dimensional optical recording materials, etc. since they have a high two-photon absorption efficiency and undergo photochromism effectively through optical absorption.
Synthesis of 2-hydroxy-8′-(hydroxymethyl)-1,1′-binaphthalene (iso-homo-binol). A new structural pattern in the binaphthyl realm
Vyskocil, Stepan,Lockhart, Stephen C.,Mitchell, William L.,Kocovsky, Pavel
, p. 907 - 916 (2007/10/03)
The title compound 7 has been synthesized in a racemic form, using Suzuki coupling (8 + 15 → 16) as the key step. Pure enantiomer (S)-(-)-7 has been obtained by carbonylation of the known bromide (S)-(+)-12 followed by reduction of the resulting methyl ester (S)-(+)-18 with LiAlH4.
Supramolecular Phosphoryl Transfer Reactions Mediated by Amidinium Phosphate Ion-Pair Complexes
Mueller, Gilbert,Duerner, Gerd,Bats, Jan W.,Goebel, Michael W.
, p. 1075 - 1092 (2007/10/02)
In order to build up simplified synthetic models of staphylococcal nuclease two derivatives of 8-phenylnaphthalene-1-carboxamidine equipped with nucleophilic side chains have been prepared (1, 2).After protonation these amidinium alcohols bind phosphodiester anions via hydrogen bonds and react within the ion-pair complexes to give zwitterionic products 27 and 28.The rate accelerations (DMF, 30 deg C) compared to the phosphorylation of noncharged alcohols are 2700-fold (2) and 930-fold (1). - Key Words: Artificial phosphodiesterase / Naphthalene, 1,8-disubstituted / Molecular Recognition / Staphylococcal nuclease, model of / Enzymes / Amidinium phosphate / Ion-Pair Complexes / Guanidine
Chemistry of 8-Substituted 1-Naphtylmethylenes and 2-Substituted Benzylidenes. A simple Entry to 1H-Cyclobutanaphthalenes
Bailey, R. J.,Card, P. J.,Shechter, H.
, p. 6096 - 6103 (2007/10/02)
Study has been made of neighobing heteroatom interaction in thermolysis and photolysis of proximally substituted aryldiazomethanes.Thus, (8-bromo-1-naphthyl)diazomethane (1c) isomerize at 132 deg C to 9-bromo- (18a), 9-iodo- (18b), and 6,9-dichloro-3H-benzindazoles (18c).Indazoles 18a and 18b are reduced by lithium aluminum hydride to 3H-benzindazole (21), identical with that from decomposition of N-(1-methyl-2-naphthyl)-N-nitrosoacetamide (19). 1-Naphthyldiazomethane (1e) does not isomerize however to 21; in benzene at -78 deg c, 1e converts to trans-bis(1-naphthyl)ethylene (22b), 1-naphthalzine (26), and 7-(1-naphthyl)cycloheptatriene (24) wich rearranges to 1-(1-naphthyl)cycloheptatriene (25) whean heated.Irradiation of 1a in ethyl ether results in trans-bis(8-bromo-1-naphthyl)ethylene (22c) and 1-bromo-1Hcyclobutanaphthalene (4a), the first aryne bridged in its peri positions by a single carbon atom moiety.Aqueous silver nitrate converts 4a tp 1H-cyclobutanaphthyl nitrate (4b) and 1-naphthaldehyde (28), presumably by ring opening of 1-hydroxy-1H-cyclobutanaphhtalene (27).Reaction of 4a with magnesium and hydrolysis of the resulting Grignard reagent yield 1H-cyclobutanaphthalene (4d), a hydrocarbon acid wich udergoes deuterium exchange at C-1 considerably slower than to acenaphthene (29) and diphenylmethane (30).Thermolysis and photolysis of diazomethane (1d) to give 2-methyl-2H-naphthothiophene (33) are of note in that methylthio participation in 8-(methylthio)-1-naphthylidene (2d) and thia-Stevens rearrangement appear to be involved. (o-Iodophenyl)diazomethane (5a) thermolyzes to trans-bis(o-iodophenyl)ethylene and o-iodobenzalazine (36); products of reaction of the iodine moiety with the carbenic center in o-iodobenzylidene (6a) were not found.Thermolysis however of (o-(methylthio)phenyl)diazpmethane (5b) results in inrtamolecular C-H insertion to yield 4,5-dihydrothiophene (37) along with trans-bisethylene (38) and o-(methylthio)benzalazine(39).Intermolecular carbenic interception does occur in photolysis of 5b iin that 2-(2-ethoxy-1-propyl)thioanisole (40) is formed along with 398 and 39.The mechanisms of the various participation processes in the above substituted 1-naphthylidenes are discussed.
