Tag: M.W=300-400

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 A rhodium-catalyzed Sonogashira-type coupling exploiting C-S functionalization: orthogonality with palladium-catalyzed variants, published in 2019, which mentions a compound: 36620-11-8, Name is Bis(norbornadiene)rhodium (I) tetrafluoroborate, Molecular C14H8BF4Rh, Synthetic Route of C14H8BF4Rh.

This report concerns the development of an efficient Sonogashira-type coupling of arylmethylsulfides and terminal alkynes to generate aryl alkyne motifs. Orthogonal reactivity between traditional Pd catalysts, and the Rh catalysts employed, results in the ability to selectively activate either the C-S bond or C-X bond through catalyst choice. The Rh-bisphosphine catalyst has further been shown to be able to effect a hydroacylation-Sonogashira tandem sequence, and in combination with further onward reactions has been used in the synthesis of heterocycles and polycyclic systems.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 36620-11-8, is researched, Molecular C14H8BF4Rh, about Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation, the main research direction is chromane preparation enantioselective; chromanylidene acetate asym hydrogenation rhodium catalyst.SDS of cas: 36620-11-8.

Rh/ZhaoPhos-catalyzed asym. hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates I (R = H, Cl, F, MeO; R1 = CO2Me, CO2Et, CO2iPr) was successfully developed to prepare various chiral 4-substituted chromanes II with high yields and excellent enantioselectivities (up to 99% yield, 98% ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 mol% catalyst loading (TON = 5000) and the hydrogenation product II (R = H, R1 = CO2Et) was easily converted to access other important compounds, II (R = H, R1 = CO2H, CH2OH) which demonstrated the synthetic utility of this asym. catalytic methodol.

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Quinuclidine – Wikipedia,
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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate(SMILESS: [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10,cas:36620-11-8) is researched.SDS of cas: 36620-11-8. The article 《Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem》 in relation to this compound, is published in Chinese Journal of Chemistry. Let’s take a look at the latest research on this compound (cas:36620-11-8).

Herein, an efficient method to reduce endocyclic enones with mol. hydrogen was reported. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%-99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

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Quinuclidine – Wikipedia,
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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: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes.HPLC of Formula: 36620-11-8.

The first highly enantioselective rhodium-catalyzed cross-addition of silylacetylenes to cyclohexadienone-tethered internal alkynes has been achieved via a tandem process: regioselective alkynylation of the internal alkynes and subsequent intramol. conjugate addition to the cyclohexadienones, affording the cis-hydrobenzofuran frameworks with good yields (up to 88% yield) and excellent enantioselectivities (90%-96% ee). This mild reaction showed perfect atom economy and broad functional group tolerance. Furthermore, a gram-scale experiment and diverse further conversions of the cyclization products were also presented.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Formula: C14H8BF4Rh. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters. Author is Lou, Yazhou; Wang, Jun; Gong, Gelin; Guan, Fanfu; Lu, Jiaxiang; Wen, Jialin; Zhang, Xumu.

The direct catalytic asym. hydrogenation of (Z)-α-dehydroamino boronate esters was realized. Using this approach, a class of therapeutically relevant alkyl-substituted α-amidoboronic esters was easily synthesized in high yields with generally excellent enantioselectivities (up to 99% yield and 99% ee). The utility of the products has been demonstrated by transformation to their corresponding boronic acid derivatives by a Pd-catalyzed borylation reaction and an efficient synthesis of a potential intermediate of bortezomib. The clean, atom-economic and environment friendly nature of this catalytic asym. hydrogenation process would make this approach a new alternative for the production of alkyl-substituted α-amidoboronic esters of great potential in the area of organic synthesis and medicinal chem.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ) is researched.Computed Properties of C14H8BF4Rh.Decultot, Ludovic; Policarpo, Rocco L.; Wright, Brandon A.; Huang, Danny; Shair, Matthew D. published the article 《Asymmetric total synthesis of C9′-epi-sinefungin》 about this compound( cas:36620-11-8 ) in ChemRxiv. Keywords: epi sinefungin modular scalable asym synthesis. Let’s learn more about this compound (cas:36620-11-8).

The natural nucleoside (+)-sinefungin, structurally similar to cofactor S-adenosyl-L-methionine (SAM), inhibits various SAM-dependent methyltransferases (MTs). Access to sinefungin analogs could serve as the basis for the rational design of small-mol. methyltransferase inhibitors. We developed a route to the unnatural C9′ epimer of sinefungin that employed a diastereoselective Overman rearrangement to install the key C6′ amino stereocenter. The ability for late stage modification is highlighted, opening an avenue for the discovery of new MTs inhibitors.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Li, Chengxi; Wan, Feng; Chen, Yuan; Peng, Henian; Tang, Wenjun; Yu, Shu; McWilliams, J. Christopher; Mustakis, Jason; Samp, Lacey; Maguire, Robert J. published an article about the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8,SMILESS:[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10 ).Safety of Bis(norbornadiene)rhodium (I) tetrafluoroborate. 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:36620-11-8) through the article.

We herein report the development of a conformationally defined, electron-rich, C2-sym., P-chiral bisphosphorus ligand, ArcPhos, by taking advantage of stereoelectronic effects in ligand design. With the Rh-ArcPhos catalyst, excellent enantioselectivities and unprecedentedly high turnovers (TON up to 10,000) were achieved in the asym. hydrogenation of aliphatic carbocyclic and heterocyclic tetrasubstituted enamides, to generate a series of chiral cis-2-alkyl-substituted carbocyclic and heterocyclic amine derivatives in excellent enantiomeric ratios. This method also enabled an efficient and practical synthesis of the Janus kinase inhibitor (R)-tofacitinib.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ) is researched.Formula: C14H8BF4Rh.Edelstein, Emma K.; Rankic, Danica A.; Dudley, Caroline C.; McMinn, Spencer E.; Adpressa, Donovon A. published the article 《Synthesis of proline analogs via Rh-catalyzed asymmetric conjugate addition》 about this compound( cas:36620-11-8 ) in ACS Catalysis. Keywords: substituted proline enantioselective diastereoselective synthesis solvent effect; dehydroproline boronic acid asym conjugate addition reaction rhodium catalyst; proline substituted free energy DFT. Let’s learn more about this compound (cas:36620-11-8).

An enantio- and diastereoselective Rh-catalyzed conjugate addition reaction for the synthesis of proline analogs is reported. A high-throughput experimentation campaign was used to identify an efficient chiral catalyst which was able to afford the desired products in high yield and with high levels of diastereo- and enantioselectivity. This method was used to afford a range of 3-substituted proline derivatives from readily available dehydroproline electrophiles and boronic acid nucleophiles.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

COA of Formula: C14H8BF4Rh. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Halogen bonding effects on the outcome of reactions at metal centres. Author is Carreras, Lucas; Benet-Buchholz, Jordi; Franconetti, Antonio; Frontera, Antonio; van Leeuwen, Piet W. N. M.; Vidal-Ferran, Anton.

Key findings regarding the effects of ligand preorganization via halogen bonding on the outcome of reactions at rhodium are reported. An unprecedented halogen bonding-mediated oxidative addition of CAr-I bonds to rhodium with efficient formation of cyclometalated species deserves special mention.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

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: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes.Category: quinuclidine.

The first highly enantioselective rhodium-catalyzed cross-addition of silylacetylenes to cyclohexadienone-tethered internal alkynes has been achieved via a tandem process: regioselective alkynylation of the internal alkynes and subsequent intramol. conjugate addition to the cyclohexadienones, affording the cis-hydrobenzofuran frameworks with good yields (up to 88% yield) and excellent enantioselectivities (90%-96% ee). This mild reaction showed perfect atom economy and broad functional group tolerance. Furthermore, a gram-scale experiment and diverse further conversions of the cyclization products were also presented.

Although many compounds look similar to this compound(36620-11-8)Category: quinuclidine, numerous studies have shown that this compound(SMILES:[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider