Author: Jessica.F

Yoshida, Tatsuki published the artcileN-Methylphenothiazine S-Oxide Enabled Oxidative C(sp²)-C(sp²) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums, Quality Control of 849062-12-0, the publication is Organic Letters (2021), 23(24), 9664-9668, database is CAplus and MEDLINE.

The development of a transition-metal-free oxidative C(sp²)-C(sp²) coupling of readily available boronic acids RB(OH)₂ (R = Ph, 2-naphthyl, 1-hexenyl, 2-(4-bromophenyl)vinyl, etc.) and organolithiums R¹Li (R¹ = 4-bromophenyl, vinyl, 2-naphthyl, etc.) via phenothiazinium ions I was reported. Various biaryl, styrene, and diene derivatives RR¹ were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions I. The mechanism of phenothiazinium formation using PTZSO was investigated using theor. calculations and experiments, which provided insight into the unique reactivity of PTZSO.

Organic Letters published new progress about 849062-12-0. 849062-12-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Bromo-5-methoxyphenyl)boronic acid, and the molecular formula is C4H4N2O2, Quality Control of 849062-12-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Fox, Martin E. published the artcileN-Alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 7. Hydroxylamine-alkyne cyclizations. Formation of cyclic nitrones and application to the synthesis of the proposed structure for (±)-acacialactam, Application of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1994), 3379-95, database is CAplus.

The cyclization of alkynylhydroxylamines to give five-, six- and seven-membered cyclic nitrones is described. A concerted intramol. ene-like pathway is proposed for the addition of the N-O-H group across the triple bond. Using 3,7-dimethyl-3,4,5,6-tetrahydro-2H-azepine 1-oxide as the starting material, the seven-membered lactam structure proposed for the natural product acacialactam was prepared and was found to be incorrect. (E)-CH₂:CHCMe(OH)CH₂CH₂CH:CMeCONH₂ is proposed as the structure for acacialactam.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Application of (4-Bromobut-1-yn-1-yl)trimethylsilane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Tirpak, Michael R. published the artcileReaction of dicobalt octacarbonyl with some acetylenic compounds, COA of Formula: C7H11Br, the publication is Journal of Organic Chemistry (1960), 687-90, database is CAplus.

In a recent investigation (CA 50, 12809i), it was reported that Co₂(CO)₈ reacted with RCCR’ (I) according to the reaction: I + Co₂(CO)₈ → RC₂R’Co₂(CO)₆ + 2CO. In the present study the effect of various groups (R and R’) upon the rate of reaction was determined The relative reactivities of various I were determined from the half-lives of their reactions. The half-lives were obtained from a plot of volume of evolved CO vs. time. The half-life of the reaction with BuCCH (II) was assigned a value of 100 on the relative reactivity scale and the relative reactivity of each of the I was calculated from: relative reactivity = t_1/2 II/t_1/2 I × 100. The average half-life for II was found to be 320 sec. The differences in the relative reactivities were not great; however, CO₂H, CO₂Me, and CH₂OH groups appeared to enhance the reactivity when attached to the triple bonded C. An anomalous behavior of certain propargyl-type halides was found and was attributed to a possible coupling reaction of these halides in the presence of Co₂(CO)₈. The following I (general methods of their preparation were given) were prepared and their relative reactivities determined (R, R’, b.p./mm., n_D/temperature, d₄/temperature, relative reactivity given): Bu, H, 70.5°/atm., 1.3970/24°, 0.7137/26°, 100; Bu, D, 70-4°/atm., 1.3970/23°, 0.722/22°, 105; Pr, Me, 82-8°/760, 1.4127/24°, 0.7401/20°, 60; Et, Et, 79-80°/760, 1.4101/23°, 0.7231/20°, 98; tert-Bu, H, 35-6°/760, 1.3743/21°, 0.6683/20°, 88; Me, Me, 29°/760, 1.3880/27°, 0.6913/20°, 56; CH₂:CMe, H, 32.5°/760, 1.4148/21°, 0.695/25°, 119; HCC(CH₂)₄, H, 32.5-3.5°/55, 1.4454/21°, 0.8195/24°, 81; Ph, H, 44-5°/22, 1.5488/22°, 0.9283/22°, 114; o-tolyl, H, 42-4°/6, 1.5460/21°, 0.9224/24°, 78; m-tolyl, H, 62-4°/18, 1.5427/21°, 0.9073/26°, 110; p-tolyl, H, 61-2°/20, 1.5455/24°, 0.9159/20°, 112; 2,4-Me₂C₆H₃, H, 69-71°/9, 1.5451/25°, 0.930/23°, 88; 2,5-Me₂C₆H₃, H, 49°/2, 1.5412/24°, 0.9180/21°, 88; 3,4-Me₂C₆H₃, H, 59-62°/3, 1.5494/25°, 0.9246/24°, 115; 2,4,6-Me₃C₆H₂, H, 62-3°/2.5, 1.5440/25°, 0.9185/25°, 20; 2,6,4-Me₂(tert-Bu)C₆H₂, H, 88-90°/2, 1.5313/23°, 0.9018/22°, 23; Ph, Ph, 150°/8 (m. 58-60°), -, -, 60; Bu, CO₂H, 116°/7, 1.4607/23, 0.9775/23°, 160; Et, (CH₂)₃CO₂H, 126-7°/8, 1.4543/28° 0.9762/28°, 60; Ph, CO₂H, -(m. 135-7°), -, -, 226; H, CH₂OH, 111-12°/atm., 1.4312/22°, 0.9338/24°, 194; H, CMe₂OH, 103°/atm., 1.4204/24°, 0.8518/28°, 177; Bu, CH₂OH, 77-8°/4, 1.4520/30°, 0.8810/28°, 120; Bu, CHMeOH, 67-9°/8, 1.4468/23°, 0.8747/24°, 123; tert-Bu, CH₂OH, 68-9°/17, 1.4421/24°, 0.8600/23°, 89; Am, CO₂Me, 96°/12, 1.4460/23, 0.9260/22, 152; Et, (CH₂)₃CO₂Me, 85-6°/9, 1.4447/21°, 0.9365/21°, 68; Me, (CH₂)₄CO₂Me, 94°/13, 1.4470/22°, 0.9552/23°, 55; H, (CH₂)₅CO₂Me, 85-6°/10, 1.4403/23°, 0.9428/24°, 92; H, OBu, 40-1°/65, 1.4000/29°, 0.8161/29°, 1; H, CH₂OMe, 60.0-60.5°/760, 1.3948/23°, 0.8410/23°, 177; H, CH₂OCPh₃, -(m. 110.5-11.0°), -, -, 186; H, 2-tetrahydropyranyloxymethyl, 57.5-8.0°/7, 1.4573/21°, 1.0148/21°, 201; H, (CH₂)₅Br, 76.5-7.0°/18, 1.4773/22°, 1.2342/22°, 87; H, (CH₂)₄I, 62-3°/8, 1.5260/28°, 1.5822/26°, 86; H, C₆H₄F-p, -(m. 25-7°), -, -, 92; H, C₆H₄Cl-p, -(m. 43.0-4.5°), -, -, 90; H, C₆H₄Cl-m, 58-60°/9, 1.5630/23°, 1.116/25°, 102; H, C₆H₄Cl-o, 65-6°/12, 1.5694/25°, 1.1249/25°, 102; H, C₆H₄Br-p, -(m. 64.5-6.0°), -, -, 100; H, CH₂Cl, 55.5°/760, 1.4335/22°, 1.0385/23°, 172; H, CH₂Br, 82°/760, 1.4928/22°, 1.5775/22°, 385; H, CMe₂Cl, 74°/760, 1.4160/25°, 0.9085/25°, 178; Bu, CH₂Cl, 56-7°/10, 1.4585/25°, 0.9470/25°, 91; Bu, CH₂Br, 64-5°/8, 1.4910/22°, 1.2427/22°, 315; Bu, CH₂I, 78-9°/7, 1.5387/25°, 1.4914/23°, 476; BrCH₂, CH₂Br, 81-2°/7, 1.5844/30°, 2.0237/29°, 325.

Journal of Organic Chemistry published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C9H11BO3, COA of Formula: C7H11Br.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Malamas, Michael S. published the artcileNovel Spirosuccinimide Aldose Reductase Inhibitors Derived from Isoquinoline-1,3-diones: 2-[(4-Bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4(11H),3′-pyrrolidine]-1,2′,3,5′(2H)-tetrone and Congeners. 1, Computed Properties of 147181-08-6, the publication is Journal of Medicinal Chemistry (1994), 37(13), 2043-58, database is CAplus and MEDLINE.

Spiro[isoquinolinepyrrolidine]tetrones I [R¹ = H, Cl, F, Br, OMe, CF₃, Me, NO₂; R² = (un)substituted benzyl, benzothiazolylmethyl, alkyl] were prepared and evaluated in vitro for their ability to inhibit glyceraldehyde reduction, using a partially purified bovine lens aldose reductase preparation, and in vivo for their ability to inhibit galactitol accumulation in the lens and sciatic nerve of galactose-fed rats. Substitution at the N-2 position of I with diverse structural substituents (i.e., aralkyl, benzothiazolylmethyl, methyl) produced several excellent series of aldose reductase inhibitors. Optimization of these new series of spirosuccinimides through structure-activity relationship (SAR) studies, including analogy from other drug series (ponalrestat, zopolrestat), led to the design of the clin. candidate I [R¹ = 6-F, R² = 2,4-F(Br)C₆H₃, II]. II exhibited exceptional oral potency in two animal models of diabetic complications, the 14-day galactose-fed and streptozocin-induced diabetic rats, with ED₅₀ values for the sciatic nerve of 0.1 and 0.09 mg/kg/day, resp. Both enantiomeric forms of II exhibited similar inhibitory activity in both in vitro and in vivo assays possibly due to their rapid interconversion. In an ex vivo experiment, the pharmacodynamic effect of II in the plasma of rats and dogs, after a single dose, appeared to be comparable to that of tolrestat.

Journal of Medicinal Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, Computed Properties of 147181-08-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Tu, Noah P. published the artcileUltrasound-assisted click chemistry in continuous flow, Application of 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is Molecular Diversity (2012), 16(1), 53-58, database is CAplus and MEDLINE.

We present a study on ultrasound-promoted click chem. reactions in a meso-flow reactor synthesis system with a copper reactor and a custom sonication piezoelec. transducer. Copper catalyzed Huisgen 1,3-dipolar cycloadditions were studied in flow with this system. Our results demonstrate that 1,4-disubstituted 1,2,3-triazole products can be generated at low temperatures and with short reaction time in good yield, due to the rate enhancement effect of sonication.

Molecular Diversity published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H13NO2, Application of 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Hu, Yueqing published the artcileSynthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT₂-selective melatonin ligands, Computed Properties of 76283-09-5, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(8), 2582-2585, database is CAplus and MEDLINE.

A series of substituted N-[3-(3-methoxyphenyl)propyl] amides were synthesized and their binding affinities towards human melatonin MT₁ and MT₂ receptors were evaluated. It was discovered that a benzyloxyl substituent incorporated at C6 position of the 3-methoxyphenyl ring dramatically enhanced the MT₂ binding affinity and at the same time decreased MT₁ binding affinity.

Bioorganic & Medicinal Chemistry Letters published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Computed Properties of 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Murakami, Yukito published the artcileHydrophobic vitamin B₁₂. XI. Preparation, characterization, and enantioselective alkylation of hydrophobic vitamin B₁₂ bearing a binaphthyl moiety, SDS of cas: 56970-78-6, the publication is Bulletin of the Chemical Society of Japan (1992), 65(11), 3094-102, database is CAplus.

Hydrophobic vitamin B₁₂ derivatives bearing a chiral binaphthyl moiety, hexamethyl 7¹-decarboxy-7¹-[(R)-2′-methoxy-1,1′-binaphthyl-2-carboxymethyl]cobyrinate perchlorate [B₁₂-BINAP(R)] and hexamethyl 7¹-decarboxy-7¹-[(S)-2′-methoxy-1,1′-binaphthyl-2-carboxymethyl]cobyrinate perchlorate [B₁₂-BINAP(S)], were prepared from cyanocobalamin. These complexes were characterized by means of electronic and CD spectroscopy as well as by cyclic voltammetry in comparison with those data for a hydrophobic vitamin B₁₂ without a binaphthyl moiety. The enantioselective alkylation of hydrophobic vitamin B₁₂ derivatives at the β-axial site was examined in methanol with various 3-bromo-2-methylpropionic esters by means of ¹H NMR spectroscopy. B₁₂-BINAP(R), and B₁₂-BINAP(S) bound (S)-2-methylpropionates more favorably than (R)-2-methylpropionates. The cause of such S-enantioselectivity was discussed with attention to stereochem. configurations of the peripheral substituents placed in the corrin ring.

Bulletin of the Chemical Society of Japan published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, SDS of cas: 56970-78-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Murakami, Yukito published the artcileHydrophobic vitamin B₁₂. V. Electrochemical carbon-skeleton rearrangement as catalyzed by hydrophobic vitamin B₁₂. Reaction mechanisms and migratory aptitude of functional groups, SDS of cas: 56970-78-6, the publication is Bulletin of the Chemical Society of Japan (1987), 60(1), 311-24, database is CAplus.

The C-skeleton rearrangements catalyzed by heptamethyl cobyrinate perchlorate (I) were investigated under electrochem. conditions. The controlled-potential electrolysis of 2,2-bis(ethoxycarbonyl)-1-bromopropane, which is considered to be a model substrate for methylmalonyl-CoA mutase, was catalyzed by I in DMF to give 1,2-bis(ethoxycarbonyl)propane as a major product at -1.5 V vs. SCE (standard C electrode)in the presence of acetic acid and at potentials more cathodic than -1.8 V vs. SCE without acetic acid in the dark. The electrochem. C-skeleton rearrangement was postulated to proceed via formation of anionic intermediates. The electrolysis of 1-bromo-2-cyano-2-ethoxycarbonylpropane, 2-acetyl-1-bromo-2-ethoxycarbonylpropane, and 1-bromo-2-[(ethylthio)carbonyl]propane with I also afforded the corresponding skeleton rearrangement products. The results indicated that substrates with 2 electron-withdrawing groups placed on the β-carbon atom with combinations of 1 carboxylic ester and 1 of carboxylic ester, acetyl, or cyano moiety readily gave the corresponding rearrangement products which were derived from individual migration of the substituent groups. Substrates with only 1 of the electron-withdrawing groups, (carboxylic ester, acetyl, or cyano) did not give any rearrangement product, but a substrate with thioester group afforded the corresponding rearrangement product. The migratory aptitude of electron-withdrawing groups decreased in the order: COSR>COR>COOR>CN. Both electronic character and steric bulkiness of the migrating groups are apparently reflected on this tendency, even though relative contributions of these effects are much dependent on the nature of β-substituents.

Bulletin of the Chemical Society of Japan published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, SDS of cas: 56970-78-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mukai, Chisato published the artcileRh(I)-catalyzed allenic Pauson-Khand reaction: first construction of the bicyclo[6.3.0]undecadienone ring system, Category: bromides-buliding-blocks, the publication is Tetrahedron (2005), 61(46), 10983-10994, database is CAplus.

The Rh(I)-catalyzed Pauson-Khand reaction of allenynes afforded the bicyclo[6.3.0]undecadienones as well as their benzo and furo derivatives E.g., [RhCl(CO)₂]₂ catalyzed the Pauson-Khand reaction of CH₂:C:C(SO₂Ph)CH₂C(CO₂Me)₂(CH₂)₃CCPh to give 43% bicyclo[6.3.0] compound I. In addition, a novel [RhCl(CO)₂]₂-catalyzed [2,3]-sigmatropic rearrangement of the sulfinic ester species of propargyl alcs. was developed. E.g., [RhCl(CO)₂]₂ catalyzed the [2,3]-sigmatropic rearrangement of PhCCCH₂OSOPh to give 63% PhSO₂CPh:C:CH₂.

Tetrahedron published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Song, Bingrui published the artcilePalladium/Copper-Catalyzed Di-α-arylation of Acetic Acid Esters, Name: Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), the publication is Advanced Synthesis & Catalysis (2011), 353(10), 1688-1694, database is CAplus.

A bimetallic palladium/copper catalyst system was found to effectively promote the diarylation of alkyl acetates with aryl halides under unprecedentedly mild conditions. The phenanthroline-copper-phosphine catalyst stabilizes the enolate intermediate to the extent that the deprotonation of esters can be achieved even with the mild base potassium phosphate. The palladium tri-tert-butylphosphine co-catalyst mediates the coupling of the resulting copper enolate with a wide variety of aryl halides with selective formation of the corresponding diarylacetic acid esters.

Advanced Synthesis & Catalysis published new progress about 25753-84-8. 25753-84-8 belongs to bromides-buliding-blocks, auxiliary class Copper, name is Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), and the molecular formula is C10H14O, Name: Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I).

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary