Month: March 2022

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Investigation of cation binding and sensing by new crown ether core substituted naphthalene diimide systems, published in 2019, which mentions a compound: 33941-15-0, mainly applied to naphthalene diimide crown ether cation binding electrostatic interaction, Electric Literature of C12H25NO5.

Crown ethers are effective at binding cations and through substitution onto the core of photoactive naphthalene diimide mols. (NDIs), cation binding can be detected via changes in UV-visible absorption and/or fluorescence emission. In this work, two new NDI-crown ether cation sensors (aza-15-crown-5 ether NDI, 5, and aza-18-crown-6 ether NDI, 6) have been synthesized and changes in UV-visible and fluorescence spectra upon addition of various cations investigated. A substantial blue shift in the UV-visible absorption of 75 nm was observed for 6 with a 1 : 1 addition of Na+ or K+, providing a clear colorimetric readout, however, no significant spectral changes were observed for 5 with the cations trialled at this level of analyte. Calcium cations do, however, elicit a response from 5 at substantially higher molar ratios, with some perturbation of the absorption spectrum observable, and an approx. six-fold increase in fluorescence emission. Theor. calculations indicate that for 6, K+ and Na+ bind to the ether oxygens resulting in a blue shift similar to that observed exptl. Ca2+ however, was found to bind quite differently with 5via both the ether oxygens and the carbonyl group on the NDI. This observation highlights how small structural changes can lead to different and unexpected behavior and that investigation of underlying binding mechanisms is important to inform the rational design of future systems.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole( cas:503538-69-0 ) is researched.COA of Formula: C38H24F4O4P2.Aida, Yukimasa; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken published the article 《Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes》 about this compound( cas:503538-69-0 ) in Organic Letters. Keywords: rhodium catalyzed asym cycloaddition diyne unsym alkene; axial chiral biaryl phosphine rhodium complex cycloaddition catalyst; multicyclic compound enantioselective preparation. Let’s learn more about this compound (cas:503538-69-0).

It has been established that a cationic rhodium(I)/axially chiral biaryl bisphosphine complex catalyzes the asym. [2 + 2 + 2] cycloaddition of α,ω-diynes with electron-rich and unstrained unsym. 1,2-disubstituted alkenes to give chiral multicyclic compounds with good yields and ee values. Interestingly, enantioselectivity highly depends on the structures of α,ω-diynes used presumably due to the presence of two distinct reaction pathways.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One-pot Synthesis of Benzoxazoles.Reference of 2-Ethylbenzo[d]oxazole.

Palladium(II) have been immobilized into the nano magnetic Fe3O4 which was functionalized with glucose in order to achieve a one-pot synthesis of 2-substituted benzoxazole derivatives with high yields in the diverse range of organic solvents. The nano catalyst is highly dispersive in polar solvents and can be easily recovered and reused for 6 runs without significant loss of its activity. Finally, the catalyst was fully characterized by FT-IR, TGA, CHN, SEM, EDX and at. absorption spectroscopy.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Name: 2,3-Dihydrospiro[indene-1,4′-piperidine] hydrochloride. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2,3-Dihydrospiro[indene-1,4′-piperidine] hydrochloride, is researched, Molecular C13H18ClN, CAS is 96651-85-3, about Efficient design, synthesis and structure-activity relationship studies of 1-(3′-substituted propyl)-4-arylpiperidines as non-peptide antagonists of nociceptin/orphanin FQ receptor: biological activities, metabolic stabilities and hERG channel bindings. Author is Hayashi, Shigeo; Ohashi, Katsuyo; Nakata, Eriko; Emoto, Chie.

Nociceptin/orphanin FQ (N/OFQ) is an endogenous heptadecapeptide that is a metabolite of precursor polypeptide (prepro-N/OFQ), and N/OFQ peptide (NOP) receptor (or opioid-receptor-like-1 receptor) is a G-protein-coupled receptor (GPCR) that is distinct from classical opioid peptide receptors, whereas the receptors share high sequence-similarities. As well, [35S]-guanosine 5′-(γ-thiotriphosphate) binding that was stimulated by N/OFQ-NOP receptor binding was not affected by various GPCR antagonists including opioid receptor antagonists. N/OFQ and NOP receptor are located in the spinal cord, the peripheral nervous systems and other peripheral tissues that are related to pain-inhibitory signal transmissions, and in the corticolimbic regions that are involved in the integration of the emotional components. Indeed, potent and selective new-class NOP receptor agonists as systemically potent analgesic against neuropathic pain and as orally potent anxiolytic with resp. unique safe-profiles have been discovered in our studies. Besides, the blockade of N/OFQ actions via N/OFQ-NOP receptor system has been displayed as anti-depression effect, anti-hyperplasia effect and anti-hypotension effect in animal model studies, which might show potential utilities of NOP receptor antagonists to modulate/attenuate N/OFQ activity for regulation of human physiologies in pharmacol. and clin. viewpoints. Hence, the design, synthesis, structure-activity relationship in vitro and structure-metabolic stability relationship in vitro of various 1-(3′-substituted propyl)-4-arylpiperidine derivatives, e.g., I, were investigated to seek and identify potent and selective new-class NOP receptor antagonists with metabolic stabilities and little hERG ion channel binding affinities by multi-viewpoint and integrated drug-design strategies, with clarifying structural features and physicochem. properties as key factors for the purposes. The unique and efficient studies, and their exclusive results and findings for the analogs are described herein.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Journal of Organic Chemistry called Copper- and Palladium-Catalyzed Cross-Coupling Reactions for the Synthesis of N-Fused Benzo[4,5]imidazo[2,1-b]thiazole Derivatives via Substituted trans-1,2-Diiodoalkenes, 1H-Benzo[d]imidazole-2-thiols, and Halobenzenes, Author is Shen, Guodong; Yang, Bingchuan; Huang, Xianqiang; Hou, Yaxin; Gao, Huan; Cui, Jichun; Cui, Chuansheng; Zhang, Tongxin, which mentions a compound: 27231-36-3, SMILESS is SC1=NC2=CC(C)=CC=C2N1, Molecular C8H8N2S, Safety of 2-Mercapto-5-methylbenzimidazole.

In the presence of CuI, 1,10-phenanthroline, and K2CO3 in DMF, 2-benzimidazolethiols underwent cross-coupling and cyclization reactions with (E)-1,2-diiodoalkenes such as (E)-PhCI:CHI to yield benzimidazothiazoles such as I (R = H) in 66-83% yields. In the presence of Pd(OAc)2, Ph3P, and Cs2CO3 in p-xylene, benzimidazothiazoles such as I (R = H) underwent arylation with aryl iodides RI (R = Ph, 2-MeC6H4, 3-MeC6H4, 4-MeC6H4, 4-ClC6H4) and bromobenzene to yield arylbenzimidazothiazoles such as I (R = Ph, 2-MeC6H4, 3-MeC6H4, 4-MeC6H4, 4-ClC6H4) in 65-96% yields. The structure of I (R = Ph) was determined by X-ray crystallog.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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: 503538-69-0, is researched, SMILESS is FC1(F)OC2=CC=C(P(C3=CC=CC=C3)C4=CC=CC=C4)C(C5=C6OC(F)(F)OC6=CC=C5P(C7=CC=CC=C7)C8=CC=CC=C8)=C2O1, Molecular C38H24F4O4P2Journal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Silver-Catalyzed Asymmetric Sakurai-Hosomi Allylation of Ketones, Author is Wadamoto, Manabu; Yamamoto, Hisashi, the main research direction is ketone allylic silane Sakurai Hosomi allylation silver chiral phosphine; homoallylic alc asym preparation; silver chiral phosphine asym Sakurai Hosomi allylation catalyst.Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

The complex of AgF and (R)-DIFLUORPHOS has been shown to be an effective catalyst for the asym. Sakurai-Hosomi allylation of simple ketones. A significant improvement of the reactivity was observed by using THF as the solvent. The catalyst turnover was increased by addition of 1 equiv of MeOH. AgF and (R)-DIFLUORPHOS predominantly formed a 1:1 complex that provided high enantioselectivity. This catalyst system can be applied to various simple ketones, and corresponding tertiary homoallylic alcs. were obtained with excellent enantioselectivities. Only 1,2-adducts were obtained from both acyclic and cyclic conjugate ketones. The regio-, diastereo-, and enantioselective crotylation has also been achieved. E- or Z-crotyltrimethoxysilane gave a similar diastereomer ratio with high enantioselectivities. This finding introduces the utility of racemic allylsilanes for the enantioselective Sakurai-Hosomi allylation reaction.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

SDS of cas: 27231-36-3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Mercapto-5-methylbenzimidazole, is researched, Molecular C8H8N2S, CAS is 27231-36-3, about A new route for the synthesis of 2-mercapto benzimidazoles. Author is Ambati, Narahari Babu; Babu, V. N. S. Ramesh; Anand, V.; Hanumanthu, P..

Bis(methylthioureido) benzenes I [R = H, Me, MeO, Cl, O2N; R1 = NHC(:S)NHMe] were prepared in 72-89% yields by treatment of benzenediamines II [R = H, Me, MeO, Cl, O2N; R1 = NH2] with Me isothiocyanate. I are refluxed in 1,4-dioxane to give benzimidazolethiols II (R = H, Me, MeO) in 89-92% yields and N,N’-dimethylthiourea as a side product.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis of furanic derivatives with CH-acid properties. Behavior of 1-(2-furyl)alkylidene derivatives of malonic acid in presence of bases, published in 1978, which mentions a compound: 3194-15-8, mainly applied to furylethylidenemalonitrile cyclodimerization; malononitrile furylethylidene cyclodimerization; tautomerism iminocyclohexenecarbonitrile derivative; cyclohexenecarbonitrile imino preparation tautomerism, Quality Control of 1-(Furan-2-yl)propan-1-one.

Reaction of MeCR:C(CN)2 (R = 2-furyl) with an equimol amount MeONa in MeOH for 8 h at 20° gave 63% the cyclodimer I. Spectral data showed that I exists as a tautomeric mixture EtCR:C(CN)2 did not undergo similar dimerization reaction.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Evindar, Ghotas; Batey, Robert A. published the article 《Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides》. Keywords: halo benzanilide cyclization benzoaxazole benzothiazole preparation.They researched the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3 ).Application of 6797-13-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6797-13-3) here.

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of o-halobenzanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramol. C-O cross-coupling of the o-halo anilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N’-dimethylethylenediamine ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples used the cyclization of o-bromo anilides, but o-iodo anilides and o-chloro anilides also undergo a reaction under these conditions. The rate of reaction of the o-halo anilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Novel and efficient heterogeneous polymer supported copper catalyst for synthesis of 2-substituted Benzoxazoles from 2-Haloanilides.Product Details of 6797-13-3.

A novel polymer supported copper complex was prepared by the immobilization of copper iodide on chem. modified polyacrylonitrile and its application in heterogeneous catalysis was described. The catalyst was prepared by easy method via synthetic modification of Polyacrylonitrile (PAN) using ethylene diamine followed by the complexation with CuI. After characterization, the complex was explored as a green and efficient heterogeneous catalyst for the synthesis of 2-benzoxazoles from 2-haloanilides. The reaction was performed without adding addnl. ligand and the catalyst shows activity over a broad range of substrates with quant. product yields. The catalyst was easily recovered by simple filtration and reused successfully for further cycle.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem