Category: 119707-74-3

Electric Literature of C20H12Br2O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Copper-Complex-Catalyzed Asymmetric Aerobic Oxidative Cross Coupling of 2-Naphthols: Enantioselective Synthesis of 3,3′-Substituted C1-Symmetric BINOLs. Author is Tian, Jin-Miao; Wang, Ai-Fang; Yang, Ju-Song; Zhao, Xiao-Jing; Tu, Yong-Qiang; Zhang, Shu-Yu; Chen, Zhi-Min.

A novel chiral 1,5-N,N-bidentate ligand I based on a spirocyclic pyrrolidine oxazoline backbone was designed and prepared; it coordinates CuBr in situ to form an unprecedented catalyst that enables efficient oxidative cross-coupling of 2-naphthols II (R3 = CHO, PhOCO, 3-FC6H4OCO, CHO, etc., R4 = H; R3 = PhOCO, R4 = Me, Br, OMe) and III (R5 = Br, Cl, CHO, PhCH2O, etc., R6 = H; R5 = H, R6 = OMe). Air serves as an external oxidant and generates a series of C1-sym. chiral BINOL derivatives IV with high enantioselectivity (up to 99% ee) and good yield (up to 87%). This approach is tolerant of a broader substrates scope, particularly substrates bearing various 3- and 3′-substituents. A preliminary investigation using one of the obtained C1-sym. BINOL product IV (R3 = CHO; R4 = R6 = H; R5 = Br) as an organocatalyst exhibited better enantioselectivity than the previously reported organocatalyst for the asym. α-alkylation of di-Et 2-aminomalonate.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

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, Journal of the American Chemical Society called Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration, Author is Alam, Rauful; Vollgraff, Tobias; Eriksson, Lars; Szabo, Kalman J., which mentions a compound: 119707-74-3, SMILESS is OC1=C(Br)C=C2C=CC=CC2=C1C3=C4C=CC=CC4=CC(Br)=C3O, Molecular C20H12Br2O2, Category: bromides-buliding-blocks.

Allylboration of ketones with γ-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.

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HPLC of Formula: 119707-74-3. 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: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Synthesis and chromatographic evaluation of new polymeric chiral stationary phases based on three (1S,2S)-(-)-1,2-diphenylethylenediamine derivatives in HPLC and SFC. Author is Payagala, Tharanga; Wanigasekara, Eranda; Armstrong, Daniel W..

Three new polymeric chiral stationary phases were synthesized based on (1S,2S)-1,2-bis(2,4,6-trimethylphenyl)ethylenediamine, (1S,2S)-1,2-bis(2-chlorophenyl)ethylenediamine, and (1S,2S)-1,2-di-1-naphthylethylenediamine via a simple free-radical-initiated polymerization in solution These monomers are structurally related to (1S,2S)-1,2-diphenylethylenediamine which is the chiral monomer used for the com. P-CAP-DP polymeric chiral stationary phase (CSP). The performance of these three new chiral stationary phases were evaluated in normal phase HPLC and supercritical fluid chromatog. and the results were compared with those of the P-CAP-DP column. All three new phases showed enantioselectivity for a large number of racemates with a variety of functional groups, including amines, amides, alcs., amino acids, esters, imines, thiols, and sulfoxides. In normal phase, 68 compounds were separated with 28 baseline separations (Rs ≥ 1.5) and in SFC, 65 compounds were separated with 24 baseline separations In total 72 out of 100 racemates were separated by these CSPs with 37 baseline separations Complimentary separation capabilities were observed for many analytes. The new polymeric CSPs showed similar or better enantioselectivities compared with the com. column in both HPLC and SFC. However, faster separations were achieved on the new stationary phases. Also, these polymeric stationary phases have good sample loading capacities while maintaining enantioselectivity.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol( cas:119707-74-3 ) is researched.Electric Literature of C20H12Br2O2.Chinnaraja, Eswaran; Arunachalam, Rajendran; Pillai, Renjith S.; Peuronen, Anssi; Rissanen, Kari; Subramanian, Palani S. published the article 《One-pot synthesis of [2+2]-helicate-like macrocycle and 2+4-μ4-oxo tetranuclear open frame complexes: Chiroptical properties and asymmetric oxidative coupling of 2-naphthols》 about this compound( cas:119707-74-3 ) in Applied Organometallic Chemistry. Keywords: one pot helicate macrocycle tetranuclear open frame copper complex; chiroptical asym oxidative coupling naphthol; binaphthyldiamine methyl diformylphenol copper salt self assembly cyclocondensation. Let’s learn more about this compound (cas:119707-74-3).

Synthesis of binuclear Cu(II) terminally closed [2+2]-double-stranded helicate-like macrocycles 1,1′,1”,2,2′,2” and 2+4-μ4-oxo tetranuclear open frame complexes 3,3′,3”,4,4′,4” are established. Adapting one-pot self-assembly technique from simple three components systems: 1,1′-binaphthyl-2,2′-diamine, 4-methyl-2,6-diformyl phenol and cupric salts, the helicate-like [2+2]- macrocyclic complexes 1-1”, 2-2” and 2+4-μ4-oxo tetranuclear complexes 3-3”, 4-4” were obtained by appropriately altering the reaction condition such as temperature and subcomponent ratio. D. Functional Theory (DFT) calculations were carried out for understanding the structural geometries, intermediates involved in the diverse formation of [2+2] and 2+4 frameworks. The single crystal x-ray structures obtained for 1′, 2 and 3 confirms the self-assembly process in line with DFT. This detailed anal. tempted us to derive a plausible mechanism for this long standing challenge in the synthesis of such macrocycles using 1,1′-binaphthyl-2,2′-diamine (BNDA) and aromatic aldehyde. The chiroptical properties of enantiopure complexes and their catalytic applications in asym. oxidative coupling of 2-naphthol to chiral 1,1′-Bi-2-naphthol (BINOL) achieved in good yield and ee were discussed.

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Bromide – Wikipedia,
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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, Macromolecules called Ring Opening Metathesis Polymerization with Binaphtholate or Biphenolate Complexes of Molybdenum, Author is Totland, Karen M.; Boyd, Thomas J.; Lavoie, Gino G.; Davis, W. M.; Schrock, Richard R., which mentions a compound: 119707-74-3, SMILESS is OC1=C(Br)C=C2C=CC=CC2=C1C3=C4C=CC=CC4=CC(Br)=C3O, Molecular C20H12Br2O2, Quality Control of (S)-3,3′-Dibromo-1,1′-bi-2-naphthol.

Several racemic or enantiomerically pure complexes of the general type Mo(CHR)(NR’)(O2R”) that contain binaphtholate or biphenolate (O2R”) ligands have been prepared and employed to ring open several achiral, racemic, or enantiomerically pure norbornenes and norbornadienes. A bimodal mol. weight distribution sometimes results from polymerization of an enantiomerically pure monomer with a racemic initiator as a consequence of a different rate of chain growth from enantiomeric metal centers. The analogous polymerization of an enantiomerically pure monomer with an enantiomerically pure initiator yields only a single polymer chain, as expected. Evaluation of the cis content of the resulting polymers suggests that cis polymer results from polymerization via syn alkylidene propagating species and that accessibility of the anti rotamer on the polymerization time scale is determined by a subtle combination of steric bulk in the biphenoxide and imido ligands. All cis polymers were found to be highly isotactic. The X-ray structures of two catalytically active species are also described. One is a THF adduct of 3,3′-diphenyl-2,2′-diolate-1,1′-dinaphthyl (anti rotamer) while the other is a base-free syn species that contains the 6,6′-dimethyl-3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diolate ligand.

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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.Ishitani, Haruro; Komiyama, Susumu; Hasegawa, Yoshiki; Kobayashi, Shu researched the compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol( cas:119707-74-3 ).SDS of cas: 119707-74-3.They published the article 《Catalytic Asymmetric Strecker Synthesis. Preparation of Enantiomerically Pure α-Amino Acid Derivatives from Aldimines and Tributyltin Cyanide or Achiral Aldehydes, Amines, and Hydrogen Cyanide Using a Chiral Zirconium Catalyst》 about this compound( cas:119707-74-3 ) in Journal of the American Chemical Society. Keywords: amino acid preparation asym Strecker imine aldehyde amine catalyst. We’ll tell you more about this compound (cas:119707-74-3).

Catalytic enantioselective Strecker-type reactions of aldimines with tributyltin cyanide (Bu3SnCN) proceeded smoothly in the presence of a novel chiral zirconium catalyst. High levels of enantioselectivities in the synthesis of α-amino nitrile derivatives with wide substrate generality were obtained via these reactions. In addition, hydrogen cyanide (HCN) was successfully used instead of Bu3SnCN as the cyanide source. Catalytic asym. Strecker amino acid synthesis starting from achiral aldehydes, amines, and HCN using a chiral zirconium catalyst has also been achieved. The three-component asym. process reported here significantly improves upon the original Strecker reaction, and has advantages over previous reactions using unstable imines (Schiff bases) as starting materials. Moreover, high yields and enantioselectivities have been obtained even in the reactions using aliphatic aldehydes, and both enantiomers of various types of α-amino acid derivatives can be prepared As demonstrations to show the utility of this reaction, efficient syntheses of homophenylalanine, leucine amide, and pipecolic acid derivatives have been performed. Finally, two novel binuclear zirconium complexes are postulated to be active chiral catalysts in the reactions of aldimines with Bu3SnCN and the three-component reactions, resp., and low loading levels of the chiral catalysts (1-2.5 mol %) have been accomplished in both cases.

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Electric Literature of C20H12Br2O2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Catalytic enantioselective [2+2]-cycloaddition reaction of 2-methoxycarbonyl-2-cyclopenten-1-one by chiral copper catalyst. Author is Takenaka, Yosuke; Ito, Hisanaka; Hasegawa, Mineki; Iguchi, Kazuo.

A new catalytic system for the enantioselective [2+2]-cycloaddition reactions of 2-methoxycarbonyl-2-cyclopenten-1-one with (alkylthio)- and (arylthio)acetylenes is described. The use of a catalytic amount (20-30 mol%) of copper(II) salts with chiral bis(pyridine) ligands was found to be effective in promoting the [2+2]-cycloaddition reaction, furnishing the corresponding bicyclic compounds in good yield and enantioselectivities. An example ligand thus prepared was 2-pyridinecarboxylic acid (1S)-[1,1′-binaphthalene]-2,2′-diyl ester. The reaction of (phenylthio)acetylene with Me 5-oxo-1-cyclopentenecarboxylate gave (1R,5S)-2-oxo-7-(phenylthio)bicyclo[3.2.0]hept-6-ene-1-carboxylic acid Me ester. The latter was converted into (-)-(1S)-3-(oxo)cyclopentaneacetic acid. (+)-(1S,5R)-2-oxo-7-(phenylthio)bicyclo[3.2.0]hept-6-ene-1-carboxylic acid Me ester, an intermediate in the total synthesis of tricycloclavulone, was also prepared

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Reference:
Bromide – Wikipedia,
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Recommanded Product: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol. 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: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Solvent effects on electronic circular dichroism spectra. Author is Robinson de Souza, Aguinaldo; Ximenes, Valdecir Farias; Morgon, Nelson Henrique.

The Electronic CD Spectrum (ECD) is a valuable tool to study the unknown absolute configuration of an optically active mol. And the comparison between exptl. data and theor. computational calculations has been a successful strategy for this study. However, the ECD spectrum is very sensitive to solvent effects that significantly change the character of the results obtained. This chapter is focused on the study of the solvent effects and their application in both exptl. and computational chem. of ECD of the compound 3,3′-dibromo-1,1′-bi-2-naphthol.

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Reference:
Bromide – 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: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol, is researched, Molecular C20H12Br2O2, CAS is 119707-74-3, about Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.Recommanded Product: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol.

The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asym. reductive transposition of the in situ generated allylic diazene. Acyclic 1,4-diene products bearing either alkyl- or aryl-substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios of up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in either a 1,4-syn or anti relation from the corresponding E- or Z-crotylboronate used in the reaction. The use of β-monosubstituted enals in the asym. traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol(SMILESS: OC1=C(Br)C=C2C=CC=CC2=C1C3=C4C=CC=CC4=CC(Br)=C3O,cas:119707-74-3) is researched.Quality Control of 4,4-Dipyridyl Disulfide. The article 《Novel binuclear chiral zirconium catalysts used in enantioselective Strecker reactions》 in relation to this compound, is published in Chirality. Let’s take a look at the latest research on this compound (cas:119707-74-3).

A novel binuclear chiral zirconium catalyst was successfully used in enantioselective Strecker reactions. The catalyst was readily prepared from zirconium t-butoxide, (R)-6,6′-dibromo-1,1′-bi-2-naphthol [(R)-6-Br-BINOL], and (R)-3,3′-dibromo-1,1′-bi-2-naphthol [(R)-3-Br-BINOL] to form a binuclear zirconium complex. It was revealed that a combination of (R)-6-Br-BINOL and (R)-3-Br-BINOL was essential in these asym. reactions and that much lower selectivities were obtained by using other combinations. Two-component [an imine and hydrogen cyanide (HCN)] and three-component (an aldehyde, an amine, and HCN) Strecker reactions proceeded smoothly in the presence of a catalytic amount of the chiral zirconium catalyst to afford the corresponding α-amino nitrile derivatives in high yields with high enantioselectivities. E.g., zirconium tert-butoxide was added to a solution of (R)-6-Br-BINOL, (R)-3-Br-BINOL, and N-methylimidazole in CH2Cl2; an HCN solution in CH2Cl2 was added at 0° and the mixture stirred for 3 h; the catalyst mixture was added to a solution of benzenepropanal and 2-amino-3-methylphenol in CH2Cl2 at -45° and stirred for 12 h to give, after workup, amino nitrile I in 85% yield and in 94% ee.

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