Category: 16400-32-1

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: 16400-32-1, is researched, SMILESS is CCC#CCBr, Molecular C5H7BrJournal, Synthesis called Oxygen-Tethered 1,6-Enynes and [4.1.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry, Author is Laher, Romain; Gentilini, Emilie; Marin, Christophe; Michelet, Veronique, the main research direction is bicyclic ether preparation olfactive property; alkenyne cycloisomerization nitrogen heterocyclic carbene gold complex catalyst.Application In Synthesis of 1-Bromo-2-pentyne.

The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of authors’ knowledge, these structures are not found in the fragrance industry, neither from natural nor synthetic pathways. NHC-gold-type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts I (X = O, S; R1 = H, Me, Bn, etc.; R2 = H, Me, Ph; R3 = H, Me; -R2R3- = -(CH2)5-; R4 = n-Pr, Ph, 4-F3CC6H4, etc.; R5 = H, n-Pr) were prepared in good to excellent yields (18-99%). Evaluation of NHC-Au complexes allowed to reach a TOF of 300 h-1. The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. Evaluations of starting materials showed a great interest in these structures with various olfactory facets. In this study, the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts are depicted.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about Asymmetric Synthesis of Alkylzincs by Rhodium-Catalyzed Enantioselective Arylative Cyclization of 1,6-Enynes with Arylzincs.HPLC of Formula: 16400-32-1.

A chiral diene-rhodium complex was found to catalyze the reaction of 1,6-enynes with ArZnCl to give high yields of 2-(alkylidene)cyclopentylmethylzincs with high enantioselectivity (95-99% ee). The enantioenriched alkylzincs were readily converted in a one-pot approach into a wide variety of functionalized products by taking advantage of their unique reactivity. The catalytic cycle involves arylrhodation of alkyne, intramol. alkenylrhodation of alkene, and transmetalation of the alkyl-rhodium intermediate into alkylzinc. Thus, e.g., treatment of enyne I with 4-MeOC6H4ZnCl and ZnCl2 in presence of chiral Rh complex afforded regioisomers II/III (88%, 20/1) after DOAc quenching, consistent with alkylzinc and arylzinc intermediates.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Orejarena Pacheco, Julio Cesar; Pusch, Stefan; Geske, Leander; Opatz, Till published an article about the compound: 1-Bromo-2-pentyne( cas:16400-32-1,SMILESS:CCC#CCBr ).Electric Literature of C5H7Br. 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:16400-32-1) through the article.

Herein, the design and development of a new one-pot and metal-free oxidative C-H activation/aza-Prins type cyclization of alkynylamines was reported. The scope of this method was demonstrated by the preparation of ten new pyrido[2,1-a]isoquinolines I [R1 = R2 = H, OMe; R3 = H, Ph, 2-thienyl, etc.; R4 = H, Et; stereo = cis, trans] in moderate to high yields (38-92%). Furthermore, a mechanistic proposal for the alkyne aza-Prins cyclization was described based on DFT calculations

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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.Kawamoto, Momoyo; Moriyama, Mizuki; Ashida, Yuichiro; Matsuo, Noritada; Tanabe, Yoo researched the compound: 1-Bromo-2-pentyne( cas:16400-32-1 ).Safety of 1-Bromo-2-pentyne.They published the article 《Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods》 about this compound( cas:16400-32-1 ) in Journal of Organic Chemistry. Keywords: pyrethrin synthesis insecticidal; cinerin synthesis insecticidal; jasmolin synthesis insecticidal. We’ll tell you more about this compound (cas:16400-32-1).

Chiral total syntheses of all six insecticidal natural pyrethrins (three pyrethrin-I and three pyrethrin-II compounds) contained in the chrysanthemum (pyrethrum) flower were performed. Three common alc. components [(S)-cinerolone, (S)-jasmololone, (S)-pyrethrolone] were synthesized: (i) Straightforward Sonogashira-type cross-couplings using available (S)-4-hydroxy-3-methyl-2-(2-propynyl)cyclopent-2-en-1-ones (the prallethrin alc.) for (S)-cinerolone (overall 52% yield, 98% ee) and (S)-pyrethrolone (overall 54% yield, 98% ee) and (ii) traditional decarboxylation-aldol condensation and lipase-catalyzed optical resolution for (S)-jasmololone (overall 16% yield, 96% ee). Two counter acid segments of [(1R,3R)-chrysanthemic acid (A) and (1R,3R)-second chrysanthemic acid precursor (B)] were prepared: (i) C(1)-epimerization of Et (±)-chrysanthemates and optical resolution using (S)-naphthylethylamine to afford A (96% ee) and (ii) concise derivatization of A to B (96% ee). All six pyrethrin esters (cinerin I/II, jasmolin I/II, pyrethrin I/II) were successfully synthesized utilizing an accessible esterification reagent (TsCl/N-methylimidazole). To investigate the stereostructure-activity relationship, all four chiral stereoisomers of cinerin I were synthesized. Three alternative syntheses of (±)-jasmololone were investigated (methods utilizing Piancattelli-rearrangement, furan-transformation, and 1-nitropropene-transformation). Insecticidal activity assay (KD50 and IC50) against the common mosquito (Culex pipiens pallens) revealed that (i) pyrethrin-I > pyrethrin-II, (ii) pyrethrin I(II) > cinerin I(II) >> jasmolin I(II), (iii) “”natural”” cinerin I >> three “”unnatural”” cinerin I compounds (apparent chiral discrimination).

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Category: tetrahydropyran. 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: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about Cu(I)- and Au(I)-catalyzed regioselective oxidation of diynes: divergent synthesis of N-heterocycles. Author is Shen, Wen-Bo; Zhang, Ting-Ting; Zhang, Meng; Wu, Jing-Jing; Jiang, Xiao-Lei; Ru, Guang-Xin; Gao, Guang-Qin; Zhu, Xiu-Hong.

Catalyst-dependent oxidative cyclization of diynes 2-NH(C(O)R4)-4-R3C6H3CCCH2N(R2)CC(R1) [R1 = Ph, 2-phenylethenyl, thiophen-3-yl, etc.; R2 = Ts, Bs, Ms, benzenesulfonyl; R3 = H, Me, Cl, Br; R4 =Me, Ac, Bz, 4-fluorophenyl, etc.]/(R2)N(CH2CCR5)CCAr [R5 = Me, Et, pentyl, 3-phenylpropyl; Ar = Ph, 4-(trifluoromethyl)phenyl, 3,5-dichlorophenyl, etc.] with 3,5-dichloropyridine N-oxide is achieved using an amide directing group. Non-polarized and aminated alkyne could be selectively activated by copper and gold, thus leading to divergent synthesis of a range of pyrroles I and dihydroindeno[1,2-c]pyrrol-3(2H)-ones II (R6 = H, Cl, Me; R7 = H, Me, F, CF3, etc.; R8 = H, Cl, Me, etc.). It should be noted that this difference might be attributed to the multicoordinated Cu center and the linearly aligned dicoordinated Au center.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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.Karuppasamy, Muthu; Vachan, B. S.; Vinoth, Perumal; Muthukrishnan, Isravel; Nagarajan, Subbiah; Ielo, Laura; Pace, Vittorio; Banik, Subrata; Maheswari, C. Uma; Sridharan, Vellaisamy researched the compound: 1-Bromo-2-pentyne( cas:16400-32-1 ).Safety of 1-Bromo-2-pentyne.They published the article 《Direct Access to 9-Chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade》 about this compound( cas:16400-32-1 ) in Organic Letters. Keywords: palladium catalyzed cascade synthesis chlorobenzofuroazepinone proparyl arylamine unsaturated ester. We’ll tell you more about this compound (cas:16400-32-1).

An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramol. syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-Bromo-2-pentyne( cas:16400-32-1 ) is researched.COA of Formula: C5H7Br.Torres-Garcia, Irene; Lopez-Martinez, Josefa L.; Martinez-Martinez, Raquel; Oltra, J. Enrique; Munoz-Dorado, Manuel; Rodriguez-Garcia, Ignacio; Alvarez-Corral, Miriam published the article 《The half-sandwich titanocene CpTiIIICl2 as efficient system for the preparation of 2,5-dihydrofurans via α-allenols》 about this compound( cas:16400-32-1 ) in Applied Organometallic Chemistry. Keywords: haloalkyne aldehyde titanium catalyst regioselective barbier type reaction; homopropargylic alc preparation; allenol preparation. Let’s learn more about this compound (cas:16400-32-1).

The half-sandwich titanocene reagent CpTiIIICl2, obtained by in-situ reduction of com. CpTiCl3 with manganese, was an excellent system for the Barbier-type reaction between aldehydes and propargylic halides, led to homopropargylic alcs. and α-allenols. An efficient and straightforward methodol. for the conversion of aldehydes into 2,5-dihydrofurans involving a two-step sequence (TiIII addition-AgI cyclization) was presented. The usefulness of the method was proved by the preparation of a Natural Product: a dihydrofuranic labdane, isolated from the leaves of Mikania sp. nov.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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: 16400-32-1, is researched, SMILESS is CCC#CCBr, Molecular C5H7BrJournal, Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov’t, Non-P.H.S., Journal of the American Chemical Society called Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature, Author is Deng, Lin; Fu, Yue; Lee, Siu Yin; Wang, Chengpeng; Liu, Peng; Dong, Guangbin, the main research direction is kinetic resolution rhodium catalyzed carbon carbon activation cyclobutanone; trans fused bicycle cyclobutanone enantioselective synthesis DFT.Computed Properties of C5H7Br.

Herein we describe the development of a highly selective kinetic resolution of cyclobutanones via a Rh-catalyzed “”cut-and-sew”” reaction with selectivity factor up to 785. This reaction takes place at room temperature with excellent efficiency. Various trans-5,6-fused bicycles and C2-substituted cyclobutanones were obtained with excellent ee’s that can be further used as chiral building blocks. DFT calculations reveal the crucial roles of the DTBM-segphos ligand in stabilizing the rate- and enantioselectivity-determining C-C oxidative addition transition state via favorable ligand-substrate dispersion interactions.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Category: tetrahydropyran. 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: 1-Bromo-2-pentyne, is researched, Molecular C5H7Br, CAS is 16400-32-1, about New 3-O-substituted xanthone derivatives as promising acetylcholinesterase inhibitors.

A new series of 3-O-substituted xanthone derivatives I (R = H, Bu, 2-butynyl, CH2Ph, etc.) were synthesized and evaluated for their anti-cholinergic activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The results indicated that the xanthone derivatives possessed good AChE inhibitory activity with eleven of them exhibiting significant effects with the IC50 values ranging from 0.88 to 1.28μM. The AChE enzyme kinetic study of 3-(4-phenylbutoxy)-9H-xanthen-9-one and Et 2-[(9-oxo-9H-xanthen-3-yl)oxy]acetate showed a mixed inhibition mechanism. A mol. docking study showed that 3-(4-phenylbutoxy)-9H-xanthen-9-one binds to the active site of AChE and interacts via extensive π-π stacking with the indole and phenol side chains of Trp86 and Tyr337, besides the hydrogen bonding with the hydration site and π-π interaction with the phenol side chain of Y72. This study revealed that 3-O-alkoxyl substituted xanthone derivatives are potential lead structures, especially 3-(4-phenylbutoxy)-9H-xanthen-9-one and Et 2-[(9-oxo-9H-xanthen-3-yl)oxy]acetate which can be further developed into potent AChE inhibitors.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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.Thadkapally, Srinivas; Farshadfar, Kaveh; Drew, Melanie A.; Richardson, Christopher; Ariafard, Alireza; Pyne, Stephen G.; Hyland, Christopher J. T. researched the compound: 1-Bromo-2-pentyne( cas:16400-32-1 ).Application of 16400-32-1.They published the article 《Rhodium-catalysed tetradehydro-Diels-Alder reactions of enediynes via a rhodium-stabilized cyclic allene》 about this compound( cas:16400-32-1 ) in Chemical Science. Keywords: isobenzofuran preparation; isoindoline preparation; indane preparation; enediyne Diels Alder reaction rhodium catalyst. We’ll tell you more about this compound (cas:16400-32-1).

Herein, tethered unconjugated enediynes R1CCCH=CHCH(R3)XCH2CCR2 [R1 = Ph, n-pentyl, 4-fluorophenyl, etc.; R2 = H, Et, Ph; R3 = H, Me, n-Pr; X = O, NTs, NNs, C(C(O)OMe)2] have been shown to undergo a facile room-temperature RhI-catalyzed intramol. tetradehydro-Diels-Alder reaction to produce highly substituted isobenzofurans, isoindolines and indane I. Furthermore, exptl. and computational studies suggest a novel mechanism involving an unprecedented and complex RhI/RhIII/RhI/RhIII redox cycle involving the formation of an unusual strained 7-membered rhodacyclic allene intermediate and a RhIII-stabilized 6-membered ring allene complex.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics