Tag: M.W=500-600

Category: esters-buliding-blocks. 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: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Desymmetrization of difluoromethylene groups by C-F bond activation. Author is Butcher, Trevor W.; Yang, Jonathan L.; Amberg, Willi M.; Watkins, Nicholas B.; Wilkinson, Natalie D.; Hartwig, John F..

Tertiary stereogenic centers containing one fluorine atom are valuable for medicinal chem. because they mimic common tertiary stereogenic centers containing one hydrogen atom, but they possess distinct charge distribution, lipophilicity, conformation and metabolic stability1-3. Although tertiary stereogenic centers containing one hydrogen atom are often set by enantioselective desymmetrization reactions at one of the two carbon-hydrogen (C-H) bonds of a methylene group, tertiary stereocenters containing fluorine have not yet been constructed by the analogous desymmetrization reaction at one of the two carbon-fluorine (C-F) bonds of a difluoromethylene group3. Fluorine atoms are similar in size to hydrogen atoms but have distinct electronic properties, causing C-F bonds to be exceptionally strong and geminal C-F bonds to strengthen one another4. Thus, exhaustive defluorination typically dominates over the selective replacement of a single C-F bond, hindering the development of the enantioselective substitution of one fluorine atom to form a stereogenic center5,6. Here the authors report the catalytic, enantioselective activation of a single C-F bond in an allylic difluoromethylene group to provide a broad range of products containing a monofluorinated tertiary stereogenic center. By combining a tailored chiral iridium phosphoramidite catalyst, which controls regioselectivity, chemoselectivity and enantioselectivity, with a fluorophilic activator, which assists the oxidative addition of the C-F bond, these reactions occur in high yield and selectivity. The design principles proposed in this work extend to palladium-catalyzed benzylic substitution, demonstrating the generality of the approach.

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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(SMILESS: C[C@@H](N(P1OC2=CC=C3C=CC=CC3=C2C4=C5C=CC=CC5=CC=C4O1)[C@@H](C6=CC=CC=C6)C)C7=CC=CC=C7,cas:415918-91-1) is researched.SDS of cas: 693-67-4. The article 《An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones》 in relation to this compound, is published in Journal of the American Chemical Society. Let’s take a look at the latest research on this compound (cas:415918-91-1).

An Ir/Zn dual catalysis has been developed for the enantio- and diastereodivergent α-allylation of unprotected α-hydroxyketones under mild conditions, in the absence of any addnl. base. The cooperative action of a chiral iridium complex derived from phosphoramidites and a chiral Zn-ProPhenol complex is most likely responsible for its high reactivity, excellent enantioselectivity (up to >99% ee), and good diastereoselectivity (up to >20:1 dr). All four product stereoisomers could be prepared from the same set of starting materials and under identical conditions by simple selection of appropriate catalyst combinations.

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

COA of Formula: C36H30NO2P. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes. Author is Zhang, Qun-Liang; Xiong, Qin; Li, Miao-Miao; Xiong, Wei; Shi, Bin; Lan, Yu; Lu, Liang-Qiu; Xiao, Wen-Jing.

Higher-order cycloadditions, particularly [8+2] cycloadditions, are a straightforward and efficient strategy for constructing significant medium-sized architectures. Typically, configuration-restrained conjugated systems were used as 8π-components for higher-order concerted cycloadditions However, for this reason, 10-membered monocyclic skeletons have never been constructed via catalytic asym. [8+2] cycloaddition with high peri- and stereoselectivity. Here, the authors accomplished an enantioselective [8+2] dipolar cycloaddition via the merger of visible-light activation and asym. palladium catalysis. This protocol provides a new route to 10-membered monocyclic architectures bearing chiral quaternary stereocenters with high chemo-, peri-, and enantioselectivity. The success of this strategy relied on the facile in situ generation of Pd-containing 1,8-dipoles and their enantioselective trapping by ketene dipolarophiles, which were formed in situ via a photo-Wolff rearrangement.

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Regio- and Enantioselective Iridium-Catalyzed Intermolecular Allylic Etherification of Achiral Allylic Carbonates with Phenoxides, the main research direction is ether aromatic allylic enantioselective regioselective preparation; carbonate allylic achiral stereoselective regioselective allylic etherification phenoxide; iridium phosphoramidite complex enantioselective regioselective intermol allylic etherification catalyst.SDS of cas: 415918-91-1.

An enantioselective and regioselective iridium-catalyzed allylic etherification is described. The reaction of sodium and lithium phenoxides R1OM (R1 = Ph, 2-MeC6H4, 4-MeOC6H4, 3-Me2NC6H4, etc.; M = Li, Na) with achiral allylic carbonates (E)-R2CH:CHCH2OCO2R3 (R2 = Pr, Ph, 2-MeOC6H4, 4-MeOC6H4; R3 = Me, Et) in the presence of 2 mol % of an iridium-phosphoramidite complex provides chiral allylic aryl ethers R2CH(OR1)CH:CH2 in high yields and with excellent levels of regio- and enantioselectivity. Lithium phenoxides containing a single substituent at an ortho, meta, or para position as well as sterically hindered phenoxides were tolerated. Reactions in THF displayed the most suitable balance of rate, regio-, and enantioselectivity.

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

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 Ir/Cu dual catalysis: Enantio- and diastereodivergent access to α,α-disubstituted α-amino acids bearing vicinal stereocenters, published in 2018-02-14, which mentions a compound: 415918-91-1, Name is (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, Molecular C36H30NO2P, COA of Formula: C36H30NO2P.

We describe a fully stereodivergent synthesis of a range of α,α-disubstituted α-amino acids via an Ir/Cu-catalyzed α-allylation of readily available imine esters. The introduction of a Cu-Phox complex-activated imine ester into the chiral iridium-catalyzed allylic allylation process is crucial for its high reactivity and excellent enantio- and diastereoselectivity (up to >99% ee and >20:1 dr). Importantly, the two chiral catalysts allow for full control over the configuration of the stereocenters, affording all stereoisomers of the desired products. The utility of this methodol. was demonstrated by synthesizing dipeptides and analogs of bioactive mols. in a stereodivergent manner.

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

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 Secondary Interactions or Ligand Scrambling? Subtle Steric Effects Govern the Iridium(I) Coordination Chemistry of Phosphoramidite Ligands, published in 2010, which mentions a compound: 415918-91-1, Name is (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, Molecular C36H30NO2P, Name: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine.

The like and unlike isomers of phosphoramidite (P*) ligands are found to react differently with iridium(I), which is a key to explaining the apparently inconsistent results obtained by us and other research groups in a variety of catalytic reactions. Thus, the unlike diastereoisomer (aR,S,S)-[IrCl(cod)(1a)] (2a; cod = 1,5-cyclooctadiene, 1a = (aR,S,S)-(1,1′-binaphthalene)-2,2′-diyl bis(1-phenylethyl)phosphoramidite) forms, upon chloride abstraction, the monosubstituted complex (aR,S,S)-[Ir(cod)(1,2-η-1a,κP)]+ (3a), which contains a chelating P* ligand that features an η2 interaction between a dangling Ph group and iridium. Under analogous conditions, the like analog (aR,R,R)-1a’ gives the disubstituted species (aR,R,R)-[Ir(cod)(1a’,κP)2]+ (4a’) with monodentate P* ligands. The structure of 3a was assessed by a combination of x-ray and NMR spectroscopic studies, which indicate that it is the configuration of the binaphthol moiety (and not that of the dangling benzyl N groups) that determines the configuration of the complex. The effect of the relative configuration of the P* ligand on its iridium(I) coordination chem. is discussed in the context of our preliminary catalytic results and of apparently random results obtained by other groups in the iridium(I)-catalyzed asym. allylic alkylation of allylic acetates and in rhodium(I)-catalyzed asym. cycloaddition reactions. Further studies with the unlike ligand (aS,R,R)-(1,1′-binaphthalene)-2,2′-diyl bis{[1-(1-naphthalene-1-yl)ethyl]phosphoramidite} (1b) showed a yet different coordination mode, i.e., the η4-arene-metal interaction in (aS,R,R)-[Ir(cod)(1,2,3,4-η-1b,κP)]+ (3b).

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

Category: esters-buliding-blocks. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Methyl-monofluorination of ibuprofen selectively increases its inhibitory activity toward cyclooxygenase-1 leading to enhanced analgesic activity and reduced gastric damage in vivo. Author is Su, Hong; Xie, Yuli; Liu, Wen-Bo; You, Shu-Li.

Newly developed monofluoromethylation reaction provided access to various bioactive mols. with an interesting monofluoromethyl unit. An iridium-catalyzed asym. version was employed for large-scale methyl-monofluorination of widely used nonsteroidal anti-inflammatory drug ibuprofen (the active S isoform). The methyl-monofluorinated ibuprofen was found to selectively inhibit cyclooxygenase-1 over cyclooxygenase-2 and surprisingly, the compound, with almost equal pharmacokinetic profile, was shown to increase analgesic activity and diminish gastric damage in animal models comparing to the parent drug ibuprofen. Therefore, methyl-monofluorination could be a useful strategy for improving efficacy and safety profile of drugs from the ‘profen’ family.

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

Recommanded Product: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine. 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: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Regio- and Enantioselective N-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles Catalyzed by Single-Component Metallacyclic Iridium Complexes. Author is Stanley, Levi M.; Hartwig, John F..

Highly regio- and enantioselective iridium-catalyzed N-allylations of benzimidazoles, imidazoles, and purines were developed. N-Allylated benzimidazoles and imidazoles were isolated in high yields (up to 97%) with high branched-to-linear selectivity (up to 99:1) and enantioselectivity (up to 98% ee) from the reactions of benzimidazole and imidazole nucleophiles with unsym. allylic carbonates in the presence of single component, ethylene-bound, metallacyclic iridium catalysts. N-Allylated purines were also obtained in high yields (up to 91%) with high N9/N7 selectivity (up to 96:4), high branched-to-linear selectivity (98:2), and high enantioselectivity (up to 98% ee) under similar conditions. Competition experiments between common amine nucleophiles and the heterocyclic nitrogen nucleophiles illustrated the effect of nucleophile pKa on the rate of the iridium-catalyzed N-allylation reactions. Kinetic studies on the allylation of benzimidazole catalyzed by metallacyclic iridium-phosphoramidite complexes, in combination with studies on the deactivation of these catalysts in the presence of heterocyclic nucleophiles, provided insight into the effects of the structures of the phosphoramidite ligands on the stability of the metallacyclic catalysts.

From this literature《Regio- and Enantioselective N-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles Catalyzed by Single-Component Metallacyclic Iridium Complexes》,we know some information about this compound(415918-91-1)Recommanded Product: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, but this is not all information, there are many literatures related to this compound(415918-91-1).

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

Reference of (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Stereoselective synthesis of 2,6-disubstituted piperidines using the iridium-catalyzed allylic cyclization as configurational switch: asymmetric total synthesis of (+)-241 D and related piperidine alkaloids. Author is Gnamm, Christian; Krauter, Caroline M.; Broedner, Kerstin; Helmchen, Guenter.

Pressing the configurational switch: Use of enantiomeric Ir catalysts allows the vinylpiperidine building blocks I (R = CH:CH2, R1 = H; R = H, R1 = CH:CH2) to be synthesized with high selectivity. Total syntheses of the dendrobate alkaloid (+)-241 D, its C6-epimer, and spruce alkaloid I (R = H, R1 = n-Pr) are presented as applications.

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Reference:
Ester – Wikipedia,
Ester – 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: 415918-91-1, is researched, SMILESS is C[C@@H](N(P1OC2=CC=C3C=CC=CC3=C2C4=C5C=CC=CC5=CC=C4O1)[C@@H](C6=CC=CC=C6)C)C7=CC=CC=C7, Molecular C36H30NO2PJournal, Article, Organic & Biomolecular Chemistry called Application of iridium catalyzed allylic substitution reactions in the synthesis of branched tryptamines and homologues via tandem hydroformylation-Fischer indole synthesis, Author is Bondzic, Bojan P.; Farwick, Andreas; Liebich, Jens; Eilbracht, Peter, the main research direction is tryptamine preparation allylic substitution iridium catalyst; hydroformylation Fischer indole synthesis iridium allylic substitution.Synthetic Route of C36H30NO2P.

Combination of enantioselective allylation reactions with a tandem hydroformylation-Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized via iridium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities. The Rh catalyzed hydroformylation step in the presence of Ph hydrazine, allows the in situ formed aldehyde to be trapped as the hydrazone. Subsequent acid catalyzed indolization furnishes the desired indole structures, e.g. I, in moderate to good yields.

There is still a lot of research devoted to this compound(SMILES：C[C@@H](N(P1OC2=CC=C3C=CC=CC3=C2C4=C5C=CC=CC5=CC=C4O1)[C@@H](C6=CC=CC=C6)C)C7=CC=CC=C7)Synthetic Route of C36H30NO2P, and with the development of science, more effects of this compound(415918-91-1) can be discovered.

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