Category: 7651-82-3

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nature of the π-electronic spectra of aromatic compounds. II. Calculation of the three π-π* absorptions of conjugated systems by the Hueckel M.O. method》. Authors are Nishimoto, Kichisuke.The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).Recommanded Product: 7651-82-3. Through the article, more information about this compound (cas:7651-82-3) is conveyed.

cf. CA 61, 3817a; 62, 3907d. The absorption wavelengths,1La, 1Lb, and 1Bb, of CHCH, CH2:CH2, C6H6, PhNH2, PhOH, PhF, C10H8 and its α-NH2, α-OH, and α-F derivatives, anthracene and its α-NH2, α-OH, and α-F derivatives, tetracene, pentacene, phenanthrene and its 1-, 2-, 3-, 4-, and 9-OH derivatives, chrysene, picene, 3,4-benzphenanthrene, benzanthracene, pyrene, C5H5N and its 2-, 3-, and 4-OH derivatives, pyridazine, pyrazine, s-triazine, s-tetrazine, quinoline and its mono-OH substituted derivatives, and isoquinoline and its mono-OH derivatives were determined and calculated, and correlated to the Hueckel mol. orbital (H.M.O.) energies. After a small modification, the relations could be applied fairly well to the calculation of the electronic spectra of the α-substituted hydrocarbons and the N-heterobenzenes. The H.M.O. theory was applicable to the prediction of the 3 π-π* absorptions of conjugated systems. Simple correlation equations (given) were particularly useful for the alternant hydrocarbons and their α-substituted derivatives having an auxochromic group and also for some N-heterocycles. The electronic spectra of these compounds were very similar to those of the parent hydrocarbons. The calculations for the β-substituted derivatives did not give good results, although the agreement between the calculated and observed values was to some extent satisfactory. These discrepancies could be attributed to the complicated configuration interaction scheme between the lower excited configurations of the mol.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Electric Literature of C9H7NO. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Isoquinolin-6-ol, is researched, Molecular C9H7NO, CAS is 7651-82-3, about Copper-catalyzed hydrolysis of bromoisoquinolines: preparation of hydroxyisoquinolines.

A complex phenomenon was observed in the process of preparing hydroxyisoquinoline through copper-catalyzed hydrolysis of bromoisoquinoline. The copper (II) complexes of hydroxyisoquinoline (L2Cu.5H2O) were characterized by high resolution mass spectra, thermogravimetric anal., IR, 1H NMR (NMR), and 2D-NMR. The Cu (II) complexes were mononuclear and coordinated with oxygen and nitrogen atom of two hydroxyisoquinoline and five water mols. in which a strong hydrogen bond was present. Two optimized methods were studied to prevent the formation of copper (II) complexes. The isoquinoline with 4, 5, 6, 7, and 8 hydroxyl substitutions were successfully prepared by copper-catalyzed hydrolysis of corresponding bromoisoquinoline and then workup by sodium sulfide or adjusted pH by dry ice or carbon dioxide gas.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Product Details of 7651-82-3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Isoquinolin-6-ol, is researched, Molecular C9H7NO, CAS is 7651-82-3, about Prototropic equilibrium tautomeric systems at and near the isoelectric point as exemplified by (thio)amide-(thio)imidoles in an amphiprotic medium. Author is Zaionts, V. I.; Gutshabash, E. Sh..

The tautomeric compositions of several title systems, e.g., BzNH2, 2-pyridinone, 2-pyridinethione, 2-quinolinone, 2-quinolinethione, and their vinylogs, were calculated, and LFER between the tautomeric equilibrium constant (pKT) and the difference between the heats of atomization of the 2 tautomers were obtained. These LFER comprised 2 groups, reflecting the type of conjugation in the mols. A method was proposed for calculating the pH interval in which the tautomeric composition remains constant

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Isoquinolin-6-ol( cas:7651-82-3 ) is researched.Related Products of 7651-82-3.Zhang, Yujiao; Xie, Kebo; Liu, Aijing; Chen, Ridao; Chen, Dawei; Yang, Lin; Dai, Jungui published the article 《Enzymatic biosynthesis of benzylisoquinoline alkaloid glycosides via promiscuous glycosyltransferases from Carthamus tinctorius》 about this compound( cas:7651-82-3 ) in Chinese Chemical Letters. Keywords: Carthamus glycosyltransferase benzylisoquinoline alkaloid. Let’s learn more about this compound (cas:7651-82-3).

Enzymic glycosylation catalyzed by glycosyltransferases (GTs) has great potential in creating diverse novel and bioactive glycosides. Herein, three new GTs (UGT84A33, UGT71AE1 and UGT90A14) from Carthamus tinctorius exhibited robust catalytic promiscuity to benzylisoquinoline alkaloids, and were used as enzymic tools in glycosylation of bioactive benzylisoquinoline alkaloids. Seven novel benzylisoquinoline alkaloids O-glycosides were synthesized with high efficiency. These studies indicate the significant potential of promiscuous GTs in synthesis of benzylisoquinoline alkaloids glycosides for drug discovery.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ultraviolet spectra of N-heterocyclic systems. II. The spectra of 5(6,7, or 8)-hydroxyisoquinolines and related compounds》. Authors are Nakanishi, Koji; Ohashi, Mamoru; Kumasaki, Shoichiro; Koike, Hisashi.The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).Synthetic Route of C9H7NO. Through the article, more information about this compound (cas:7651-82-3) is conveyed.

cf. CA 54, 17412d; 55, 15113f. The mold pigment, monascorubrin, yields a degradation product monascaminone, apparently an isoquinoline derivative hydroxylated at the 5-, 6-, 7-, or 8-position. These 4-isoquinolinols, the 6- and 7-OMe, and methiodides of the 5-, 7-, and 8-OH compounds (I, II, and III, resp.) were synthesized and the ultraviolet spectra determined in neutral(excepting I, II, and III), 0.1N HCl, and 0.1N NaOH- MeOH solutions For preparation of I-III, 100 mg. of the resp. OH compound was refluxed 1 hr. in 10 ml. 1:1 Me2CO-C6H6 with 3 ml. methyl iodide. The recrystallized (EtOH) products m. 235-7, 218-20, and 217-19°, resp. The ultraviolet spectra of I, II, and III were given. Also tabulated were Δλmax between ionic species of 7- and 8-hydroxyisoquinolines, and classification of ultraviolet spectra of hydroxyand hydroxyisoquinolines, all in MeOH. W. A. Peabody

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Reference of Isoquinolin-6-ol. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Isoquinolin-6-ol, is researched, Molecular C9H7NO, CAS is 7651-82-3, about Exploration of the linkage elements of porcupine antagonists led to potent Wnt signaling pathway inhibitors. Author is Dong, Yan; Li, Kehuang; Xu, Zhixiang; Ma, Haikuo; Zheng, Jiyue; Hu, Zhilin; He, Sudan; Wu, Yiyuan; Sun, Zhijian; Luo, Lusong; Li, Jiajun; Zhang, Hongjian; Zhang, Xiaohu.

The Wnt signaling pathway is a pivotal developmental pathway. It operates through control of cellular functions such as proliferation, differentiation, migration and polarity. Aberrant Wnt signaling has been implicated in the formation and metastasis of tumors. Porcupine is a component of the Wnt signaling pathway. It is a member of the membrane-bound O-acyltransferase family of proteins. Porcupine catalyzes the palmitoylation of Wnt proteins, a process which is essential to their secretion and activity. Here we report a novel series of compounds obtained by a scaffold hybridization strategy from two known porcupine inhibitor classes. The leading compound 62 demonstrated subnanomolar (IC50 0.11 nM) inhibition of Wnt signaling in a paracrine cellular reporter gene assay. Compound 62 also potently inhibited Wnt secretion into culture medium, an indication of direct inhibition of the porcupine protein. Furthermore, compound 62 showed excellent chem., plasma and liver microsomal stabilities. Collectively, these results strongly support further optimization of this novel scaffold to develop better Wnt pathway inhibitors.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Product Details of 7651-82-3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Isoquinolin-6-ol, is researched, Molecular C9H7NO, CAS is 7651-82-3, about Correlation between electronic structure and corrosion-inhibiting properties of isoquinoline and its derivatives. Author is Luo, Ming-Dao; Bi, Gang; Kuang, Fu-Gui; Yao, Lu-An; Yan, Xiao-Ci.

The corrosion-inhibiting efficiencies of isoquinoline and its hydroxyl and carboxyl derivatives on Fe electrode in HCl solution have been determined with electrochem. method. Their structure parameters were obtained by means of HMO and CNDO/2 methods. It is found that the less the net charge and π charge of N atom has, the more the inhibition efficiency is. As the net charge sum of six atoms in pyridine ring increases, the efficiency increases. It is possible that the mols. of the inhibitors were adsorbed on the surface of Fe electrode in horizontal state.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Isoquinolin-6-ol, is researched, Molecular C9H7NO, CAS is 7651-82-3, about Photocatalytic N-heteroarylation of aldehydes via formyl C-H activation, the main research direction is photoredox catalyst heteroarylation aldehyde formyl carbon hydrogen activation; secondary alc aldehyde heteroarylation photoredox catalyst.Product Details of 7651-82-3.

A formyl C-H addition of N-heteroaromatics to aldehydes was achieved using a binary hybrid catalyst system comprising an acridinium photoredox catalyst and a thiophosphoric acid organocatalyst. The reaction proceeded through the following sequence: (1) photoredox-catalyzed single-electron oxidation of a thiophosphoric acid catalyst to generate a thiyl radical, (2) cleavage of the formyl C-H bond of the aldehyde substrates by a thiyl radical acting as a hydrogen atom transfer catalyst to generate acyl radicals, (3) Minisci-type addition of the resulting acyl radicals to N-heteroaromatics, and (4) a spin-center shift, photoredox-catalyzed single-electron reduction, and protonation to produce secondary alc. products. This metal-free hybrid catalysis proceeded under mild conditions for a wide range of substrates, including isoquinolines, quinolines, and pyridines as N-heteroaromatics, as well as both aromatic and aliphatic aldehydes, and tolerated various functional groups. The reaction was applicable to late-stage derivatization of drugs and their leads.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Gilman, Henry; Gainer, Gordon C. published an article about the compound: Isoquinolin-6-ol( cas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1 ).HPLC of Formula: 7651-82-3. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:7651-82-3) through the article.

cf. C.A. 41, 4152c. p-H2NC6H4Li (prepared from 0.66 mole BuLi and 0.22 mole p-B1C6H4NH2 in ether), treated with 0.44 mole isoquinoline in an equal volume of ether (at a rate to maintain refluxing), the mixture refluxed 12 hrs., and the orange residue in 40 cc. PhNO2 heated 1.5 hrs. at 190°, gives 67-70% 1-(p-aminophenyl)isoquinoline (I), m. 191-2°. 1-(p-Nitrophenyl)-3,4-dihydroisoquinoline (Rodinov and Yavorskaya, C.A. 35, 6592.5) (2 g.) and 1 g. Pd black, heated 2 hrs. at 190-200°, give 60% 1-(p-nitrophenyl)isoquinoline, m. 155-6°; reduction in absolute EtOH over Raney Ni at 95-100°/3 atm. gives 70% I. 5-Aminoisoquinoline (50 g.) and 39.9 g. (CH2Ac)2 give 83% 5-(2,5-dimethyl-1-pyrryl)isoquinoline (II), m. 83-4° (picrate, yellow, m. 174-5°); 4-isomer m. 77-8°, 97% [prepared with 2 moles (CH2Ac)2]. The following derivatives of isoquinoline were prepared by the method used for I: 1-p-tolyl, m. 71-2°, 55% crude yield; 1-(p-dimethylaminophenyl), m. 114.5-15°, 55% (picrate, scarlet-red, m. 220-1°); 1-[p-(2,5-dimethyl-1-pyrryl)phenyl], m. 159-60°, 45%; 1-(p-methoxyphenyl)-5-(2,5-dimethyl-1-pyrryl), dark red, viscous oil, b2 222-8°, 38%; 1-(p-mercaptophenyl), whose HCl salt was pale yellow, m. 271-2°. p-(2,5-Dimethyl-1-pyrryl)phenyllithium and II give 31% 1-[p-(2,5-dimethyl-1-pyrryl)phenyl]-5-(2,5-dimethyl-1-pyrryl)isoquinoline, m. 214-15°. 4-Bromoisoquinoline (10.5 g.), 5 g. CuSO4, 4.1 g. Cu bronze, and 31.3 g. NaOH in 17 cc. H2O, heated 12 hrs. at 210°, give 61% 4-hydroxyisoquinoline, m. 223° (picrate, yellow, m. 243-4°). p-BrC6H4NH2 (34.4 g.) and 30 g. Et2N(CH2)3Cl, heated 6 hrs. at 150-60°, give 52% p-(3-diethylaminopropylamino)phenylbromide (III), b0.2 135-7°, nD20 1.5530, d2020 1.178. p-BrC6H4NHSO2Ph (156 g.) and 41.5 g. K2CO3 at 150°, treated cautiously with 90 g. Et2N(CH2)3Cl and heated 6 hrs. at 150-60°, give 62% III; di-HCl salt m. 185-6°.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 7651-82-3, is researched, SMILESS is OC1=CC2=C(C=NC=C2)C=C1, Molecular C9H7NOJournal, Comparative Study, Article, Journal of Antibiotics called Cephalosporins having a heterocyclic catechol in the C3 side chain. II. Improvement of pharmacokinetic profile, Author is Iimura, Seiji; Imae, Kiyoto; Hasegawa, Toshifumi; Okita, Takaaki; Tamaoka, Masami; Murata, Shinji; Kamachi, Hajime; Kamei, Hideo, the main research direction is cephalosporin heterocyclic catechol preparation bactericide.Category: catalyst-palladium.

Cephalosporins I (R = H, Me; R1 = heterocyclic catechol] were synthesized. I (R = H, Me, R1 = 6,7-dihydroxyisoquinolin-2-yl) showed very high and prolonged blood levels after i.m. administration to mice and higher in vivo antibacterial activity than expected from their in vitro activity. I (R = H, R1 = 6,7-dihydroxyisoquinolin-2-yl) gave well-balanced in vitro and in vivo antibacterial spectra including anti-methicillin-resistant Staphylococcus aureus (MRSA) activity. I (R = Me, R1 = 6,7-dihydroxyisoquinolin-2-yl) also showed good in vitro and in vivo activities against Gram-pos. bacteria, especially against S. aureus A15036, a strain of MRSA, the in vivo activity being comparable to vancomycin but was lacking in anti-pseudomonal activity.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method