Heterocyclic Building Blocks-Tetrahydrofuran

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Identification of monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate in nature by high performance liquid chromatography-tandem mass spectrometry, published in 2004-06-02, which mentions a compound: 77341-67-4, Name is 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid, Molecular C14H24O4, SDS of cas: 77341-67-4.

Menthol, menthone, and other natural compounds provide a cooling effect and a minty flavor and found wide application in chewing gum and oral care products. Monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate provide a cooling effect without the burning sensation associated with menthol. Addnl., because they do not have a distinct flavor, they can be used in applications other than mint flavors. Because these menthyl esters were not reported in nature, the authors undertook to identify a natural source for these cooling compounds Using HPLC-tandem mass spectrometry, monomenthyl succinate was identified in Lycium barbarum and Mentha piperita, and monomenthyl glutarate and dimenthyl glutarate were identified in Litchi chinensis. The identifications were based on the correlation of mass spectrometric and chromatog. retention time data for the menthyl esters in the extracts with authentic standards which resulted in a 99.980% confidence in the identifications.

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Tetrahydrofuran | (CH2)3CH2O – PubChem

Application In Synthesis of Methyl 6-bromonicotinate. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines using asymmetric protonation: a method development and mechanistic study. Author is Ashford, Matthew W.; Xu, Chao; Molloy, John J.; Carpenter-Warren, Cameron; Slawin, Alexandra M. Z.; Leach, Andrew G.; Watson, Allan J. B..

A catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines is reported. A chiral Bronsted acid promotes aza-Michael addition to fluoroalkenyl heterocycles to give a prochiral enamine intermediate, which undergoes asym. protonation upon rearomatization [e.g., I + aniline → II (82%, 96:4 R:S)]. The reaction accommodates a range of azaheterocycles and nucleophiles, generating the C-F stereocenter in high enantioselectivity, and is also amenable to stereogenic C-CF3 bonds. Extensive DFT calculations have provided insight into the reaction mechanism and the origin of catalyst selectivity. Crystal structure data shows the dominance of non-covalent interactions in the core structure conformation, enabling modulation of the conformational landscape. Ramachandran-type anal. of conformer distribution and protein data bank mining has indicated benzylic fluorination using this approach has potential for improved potency in several marketed drugs.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

COA of Formula: C7H6ClNO. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Catalytic Asymmetric Cascade Using Spiro-Pyrrolidine Organocatalyst: Efficient Construction of Hydrophenanthridine Derivatives. Author is Tian, Jin-Miao; Yuan, Yong-Hai; Xie, Yu-Yang; Zhang, Shu-Yu; Ma, Wen-Qiang; Zhang, Fu-Min; Wang, Shao-Hua; Zhang, Xiao-Ming; Tu, Yong-Qiang.

In the presence of a nonracemic azaspirononane and DMAP, ortho-aminoaryl-α,β-unsaturated ketones such as I underwent diastereoselective and enantioselective tandem Michael addition and aldol condensation reactions with α,β-unsaturated aldehydes such as (E)-RCH:CHCHO (R = Ph, 2-MeOC6H4, 3-MeOC6H4, 4-MeOC6H4, 4-ClC6H4, 4-BrC6H4, 4-FC6H4, 4-O2NC6H4, 2-thienyl, 2-furanyl, EtO2C, Me) to yield tetrahydrophenanthridinones such as II (R = Ph, 2-MeOC6H4, 3-MeOC6H4, 4-MeOC6H4, 4-ClC6H4, 4-BrC6H4, 4-FC6H4, 4-O2NC6H4, 2-thienyl, 2-furanyl, EtO2C, Me) with trans-ring junctions in 36-52% yields and in 88->99% ee. When ortho-aminoaryl-α,β-unsaturated ketones with two substituents ortho to the unsaturated ketone moiety were reacted with α,β-unsaturated aldehydes, tetrahydrophenanthridinones such as III (R1 = Br, Cl, Me) with cis-ring junctions were formed in 35-46% yields and in 78-99% ee. II (R = Ph) was prepared on gram scale using this method.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Some aspects of the pharmacological activity of a new theophyllinic: 1-hexyl-3,7-dimethylxanthine (SK-7), published in 1960, which mentions a compound: 1028-33-7, Name is 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione, Molecular C13H20N4O2, Recommanded Product: 1028-33-7.

The vascular action of theophylline (I) and its derivatives and the lipotropic and antieholesterol (II) activity of I have been investigated. SK-7 reduced the amplitude of the cardiogram of isolated rabbit hearts to an extent roughly proportional to the dosage, but the effect was brief; only a dose of 500 γ of SK-7, after a brief period of inhibition, succeeded in restoring the amplitude of the tracing to a level slightly superior to that of the normal. While a dose of SK-7 of 1 mg./kg. body weight only slightly affected the arterial pressure of anesthetized dogs, a dose of 10 mg./kg. was definitely hypotensive, with a vasodilatory effect on the cerebral circulation. SK-7 increased the capacity of the vessels in the posterior portions of the rabbit and protected the rat against both gangrene in the tail and cyanosis. A protective influence of SK-7 against hyperlipide and hyper-II steatosis in the liver of rats has been demonstrated. Contrary to other derivatives of I, SK-7 has almost no effect on cardiac or coronary activity, and has a strong cerebral vasodilatory action. Its hypotensive and peripheral vasodilatory activities were typical of many xanthine compounds

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Tetrahydrofuran | (CH2)3CH2O – PubChem

Recommanded Product: 2-Amino-5-chlorobenzaldehyde. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about Molecular Iodine-Catalysed Benzylic sp3 C-H Bond Amination for the Synthesis of 2-Arylquinazolines from 2-Aminobenzaldehydes, 2-Aminobenzophenones and 2-Aminobenzyl Alcohols. Author is Deshmukh, Dewal S.; Bhanage, Bhalchandra M..

Mol. iodine catalyzed benzylic sp3 C-H bond amination has been developed for the synthesis of quinazolines I (R = H, Ph; R1 = H, 6-Cl, 6,8-Br2; R2 = 4-chlorophenyl, pyridin-3-yl, furan-2-yl, etc.) from 2-aminobenzaldehydes such as 2-amino-5-chlorobenzaldehyde, 2-aminobenzaldehyde, 2-amino-3,5-dibromobenzaldehyde and 2-aminobenzophenones such as 2-aminobenzophenone, 2-amino-5-chlorobenzophenone with benzylamines RCH2NH2. The use of oxygen as a green oxidant combined with the transition-metal-, additive- and solvent-free conditions makes the methodol. economical and greener. The lack of aqueous work up also enhances the efficiency of this protocol. A series of 2-arylquinazolines I was synthesized in good to excellent yields by using the developed protocol. The series of 2-aminobenzyl alc. could also be employed to prepare the corresponding quinazoline derivatives

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Methyl 6-bromonicotinate( cas:26218-78-0 ) is researched.Category: tetrahydrofurans.Young, Tom A.; Silcock, Joseph J.; Sterling, Alistair J.; Duarte, Fernanda published the article 《autodE: Automated Calculation of Reaction Energy Profiles- Application to Organic and Organometallic Reactions》 about this compound( cas:26218-78-0 ) in Angewandte Chemie, International Edition. Keywords: organic organometallic compound potential energy surface machine learning; automation; reaction mechanisms; sampling; transition states. Let’s learn more about this compound (cas:26218-78-0).

Calculating reaction energy profiles to aid in mechanistic elucidation has long been the domain of the expert computational chemist. Here, we introduce autodE (), an open-source Python package capable of locating transition states (TSs) and min. and delivering a full reaction energy profile from 1D or 2D chem. representations. autodE is broadly applicable to study organic and organometallic reaction classes, including addition, substitution, elimination, migratory insertion, oxidative addition, and reductive elimination; it accounts for conformational sampling of both min. and TSs and is compatible with many electronic structure packages. The general applicability of autodE is demonstrated in complex multi-step reactions, including cobalt- and rhodium-catalyzed hydroformylation and an Ireland-Claisen rearrangement.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Name: Methyl 6-bromonicotinate. 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: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI. Author is Liu, He; Wu, Jian; Jin, Yuxuan; Leng, Xuebing; Shen, Qilong.

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qual. and quant. studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligand-less [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about The reaction of nucleic acids with bromine.Synthetic Route of C5H4BrN5O.

Com. preparations of ribonucleic acid (RNA) from yeast and of deoxyribonucleic acid (DNA) from sperm, as well as high mol. DNA isolated from thymus reacted in aqueous solution with Br at temperature down to -35°. The mol. weight of brominated RNA decreased by about 15%. The nucleic acids were hydrolyzed in 70% HClO4. Paper chromatography of the products revealed the presence of 5-bromouracil, 5-bromocytosine and 8-bromoguanine. There was no indication that Br reacted with adenine or with the pentoses. Ribonuclease attacked the brominated products in the same way as normal RNA. Ultraviolet spectra of Brcontg. acids differed slightly from the original material, but infrared spectra in the range of 6.3-7.3 μ were markedly different.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 8-Bromoguanine( cas:3066-84-0 ) is researched.Computed Properties of C5H4BrN5O.Yoneyama, Toshie; Wilson, Lisa M.; Hatakeyama, Kazuyuki published the article 《GTP Cyclohydrolase I Feedback Regulatory Protein-Dependent and -Independent Inhibitors of GTP Cyclohydrolase I》 about this compound( cas:3066-84-0 ) in Archives of Biochemistry and Biophysics. Keywords: GTP cyclohydrolase I inhibitor GFRP protein guanine derivative; feedback regulatory protein inhibitor GTP cyclohydrolase I. Let’s learn more about this compound (cas:3066-84-0).

GTP cyclohydrolase I feedback regulatory protein (GFRP) mediates the feedback inhibition of GTP cyclohydrolase I activity by (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin (BH4) through protein complex formation. Since guanine and BH4 have a common pyrimidine ring structure, we examined the inhibitory effect of guanine and its analogs on the enzyme activity. Guanine, 8-hydroxyguanine, 8-methylguanine, and 8-bromoguanine inhibited the enzyme activity in a GFRP-dependent and pH-dependent manner and induced complex formation between GTP cyclohydrolase I and GFRP. The type of inhibition by this group is a mixed type. All these properties were shared with BH4. In striking contrast, inhibition by 8-azaguanine and 8-mercaptoguanine was GFRP-independent and pH-independent. The type of inhibition by 8-azaguanine and 8-mercaptoguanine was a competitive type. The two compounds did not induce complex formation between the enzyme and GFRP. These results demonstrate that guanine compounds of the first group bind to the BH4-binding site of the GTP cyclohydrolase I/GFRP complex, whereas 8-azaguanine and 8-mercaptoguanine bind to the active site of the enzyme. Finally, the possible implications in Lesch-Nyhan syndrome and Parkinson diseases of the inhibition of GTP cyclohydrolase I by guanine and 8-hydroxyguanine are discussed. (c) 2001 Academic Press.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nucleosides and nucleotides. XXX. Syntheses of 8-substituted guanosine derivatives》. Authors are Ikehara, Morio; Muneyama, Kei.The article about the compound:8-Bromoguaninecas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O).Computed Properties of C5H4BrN5O. Through the article, more information about this compound (cas:3066-84-0) is conveyed.

cf. CA 64, 14255f. 8-Bromoguanosine (I) was converted to 8-mercaptoguanosine by the method of Holmes and Robins (CA 60, 14584c), and was methylated with methyl iodide to afford 8-methylthioguanosine (II). In addition, 8-ethylthioguanosine was obtained directly by reaction of I with ethyl mercaptide in ethanol. II was oxidized either with N-chlorosuccinimide or with H2O2 (H2O2, in limited amount, being preferable) to afford 8-(methylsulfonyl)guanosine (III). When III was heated at 80° in 0.1N HCl 4 hrs., 8-methylsulfonylguanine (IV) (but not an N-oxide derivative) was obtained. Treatment of III with 0.1N NaOH at 100° 3 hrs. also gave IV. When III was kept at 30° 40 hrs. in dimethyl sulfoxide with excess Na tert-butoxide, a substance having λ (H)+ 256, 284 mμ; λ(OH)- 286 mμ was obtained, accompanied by a small amount of IV. The former compound contained S and D-ribose moieties, and it was deduced from its uv properties that the guanosine ring in III had been cleaved. Its absorption could be explained if a bathochromic shift of approx. 10-20 mμ, which is generally observed by the substitution of a methyl sulfonyl group at the 8-position of guanosine, was added to the absorption spectra of 4-aminoimidazolecarboxamide 1-p-riboside (λ(H+) 267, 240 mμ; λ(OH-) 267 mμ). The pKa value of III (8.3) is much higher than that of guanosine (9.2-9.5). The easy dissociation of N’-H of III would render the pyrimidine ring more susceptible to the nucleophilic attack of tert-butoxide. Under similar reaction conditions guanosine did not react with tert-butoxide. When III was treated with Na methoxide in methanol at 130-50°, 8-methoxyguanosine was obtained, the structure of which was confirmed by comparison with a sample obtained from I. 8-Dimethylaminoguanosine was prepared by heating I with dimethylamine in methanol at 120-30° 5 hrs. It is concluded that nucleophilic substitution occurred smoothly in I, as expected in the case of aromatic halo compound activated by ο- or p-electron attracting groups. However, in the case of III the strong electron-attracting nature of the methylsulfonyl group at position 8 caused a nucleophilic attack on N1 or N3, and the subsequent cleavage of the pyrimidine ring. Moreover, acidic hydrolysis easily cleaved III at the glycosidic linkage, whereas 8-hydroxypurine D-ribonucleoside is resistant to such cleavage. 14 references.

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Tetrahydrofuran – Wikipedia,
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