Author: Jessica.F

Arbuzov, B. A. published the artcileReaction of some chloro and bromo derivatives with sodium diethyl phosphite, Formula: C6H12Br2, the publication is Sbornik Statei po Obshchei Khimii (1953), 1144-8, database is CAplus.

(EtO)₂PONa from 0.9 g. Na and 5.35 g. (EtO)₂POH in Et₂O was treated with 10 g. Ph₂CHBr in Et₂O-C₆H₆; after 2 hrs. on the steam bath the filtered solution gave on evaporation 61.33% (CHPh₂)₂ and 5.3 g. yellow oil. No reaction took place when (EtO)₂PONa, prepared as above, was treated with Ph₂CHCl; the reaction also failed in hot (iso-Am)₂O. The reaction did proceed in refluxing MePh (2 hrs.), yielding (EtO)₂POH, Ph₂CHOH, (Ph₂CH)₂O, and a low yield of Ph₂CHP(O)(OEt)₂, b₄ 184-8°, d₀²⁰ 1.12775, n_D²⁰ 1.5450, m. 38-40°; hydrolyzed with 10% HCl 8 hrs. at 170-5° in a sealed tube, it gave the free acid, m. 223-5° (from H₂O). Addition of 8 g. (EtO)₃P in Et₂O to 12 g. Ph₂CHBr in Et₂O, followed by refluxing 1 hr. gave 43.6% yield of the same product, b₂ 180-1°, d₀²⁰ 1.1287, n_D²⁰ 1.5445, which slowly solidified and m. 39-40°; hydrolysis with 10% HCl at 150-80° gave the free acid, m. 227-8°. Addition of 13.8 g. PhCH₂Cl to (EtO)₂ONa from 15.6 g. ester in Et₂O, followed by 0.5 hr. reflux gave 49.35% PhCH₂P(O)(OEt)₂, b₁₁ 153-4°, d₀⁰ 1.1200, n_D²⁰ 1.4965; hydrolysis gave the free acid, m. 169-70° (from EtOH). Similar reaction with PhCH₂Br gave 44% yield of the same ester, b₁₂ 153-5°, d₀⁰ 1.1189, n_D²⁰ 1.4892, while PhCH₂I gave 21.1% yield of the same ester. To (EtO)₂PONa (from 15.85 g. ester) in Et₂O was added 14 g. (Me₂CBr)₂ resulting in a rapid reaction (7 min.); after filtration the mixture yielded 50% Me₂C:CMe₂.

Sbornik Statei po Obshchei Khimii published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Formula: C6H12Br2.

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

Negishi, Eiichi published the artcileMetal promoted cyclization. 18. Novel cycloalkylation reactions of (ω-halo-1-alkenyl)metal derivatives. Synthetic scope and mechanism, SDS of cas: 69361-41-7, the publication is Journal of the American Chemical Society (1988), 110(16), 5383-96, database is CAplus.

(ω-Haloalkenyl)metals undergo both σ- and π-type cyclization reactions. The σ-cycloalkylation reaction, which has so far been observed only with alkenyllithiums, provides 3- through 7-membered rings in high yields. It requires the cis relationship between Li and the ω-haloalkyl group in the cyclization step. The presence of a trialkylsilyl group on the Li-bearing C atom facilitates configurational isomerization. However, it is not necessary for cyclization. The reaction proceeds with retention of regiochem. The cycloalkylation reactions of (ω-halo-1-silyl-1-alkenyl)metals containing Al, Zn, Zr, or Si, on the other hand, proceed via π-type cyclization processes. Thus, cyclization of X(CH₂)₂CMe:C(SiMe₃)(AlMe₂), prepared by the reaction of X(CH₂)₂CCSiMe₃ (X = Cl, Br, iodo, 4-MeC₆H₄SO₂) with Me₃Al in presence of (η⁵-C₅H₅)₂ZrCl₂ in CH₂Cl₂, gave 2-methyl-1-(trimethylsilyl)cyclobutene. The relative ease of ring formation with respect to ring size is 3 and 4 ≫ 5 < 6. Formation of cyclobutenylsilanes is nonregiospecific. The stereochem. of alkenylmetal intermediates is unimportant, but the presence of a silyl group as the second metal group is necessary. The reaction can be inhibited by some polar solvents, such as THF. All of these facts can be accommodated by π-cyclization mechanisms and Baldwin’s cyclization rules.

Journal of the American Chemical Society 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, SDS of cas: 69361-41-7.

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

Negishi, Eiichi published the artcileNovel silicon-promoted cycloalkylation of alkenylmetal derivatives, Category: bromides-buliding-blocks, the publication is Journal of the American Chemical Society (1983), 105(20), 6344-6, database is CAplus.

Two novel cycloalkylation reactions of alkenylmetals, in which Si plays subtle but critical roles, are described. Such cycloalkylation reactions appear to be unprecedented. Significantly, neither appears to be affected by the stereochem. integrity of alkenylmetal intermediates. Together, they provide novel and convenient routes to cycloalkenylsilanes. X(CH₂)₂CCSiMe₃ (I, X = C, Br, I) are either hydroaluminated with diisobutylaluminum hydride or carboaluminated with Me₃Al-Cl₂ZrCp₂ in nonpolar solvents, such as hexane, benzene or (CH₂Cl)₂, and were converted into 1-trimethylsilyl-1-cyclobutene and its derivatives in 80-100% yields. The available data suggest that the reaction involves a π-type process via cyclopropylcarbinyl cationic series. A similar reaction occurs with 1-trimethylsilylpropargyl bromide. Its reaction with Me₃Al-Cl₂ZrCp₂ gives II instead of III. Application of the method to the preparation of five- and six-membered alkenylsilanes have not been successful. Fortunately, an alternate procedure was developed which presumably involves a σ-type process. Thus, treatment of appropriate ω-bromo-1-trimethylsilyl-1-iodo-1-alkenes with 2 equivalent of Me₃CLi in ether at -78° followed by gradual warming has produced 1-trimethyl-1-cycloalkenes containing four-, five-, and six-membered rings in 64-81% yields. The synthetic utility of these cyclization reactions may be indicated by a 4-step conversion of I to grandisol (IV) as a 2:1 mixture of the Z and E isomers in overall 40% yield.

Journal of the American Chemical Society 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

Nikiforov, Petar O. published the artcileFragment-Sized EthR Inhibitors Exhibit Exceptionally Strong Ethionamide Boosting Effect in Whole-Cell Mycobacterium tuberculosis Assays, Name: (2-Bromoethyl)cyclopentane, the publication is ACS Chemical Biology (2017), 12(5), 1390-1396, database is CAplus and MEDLINE.

Small-mol. inhibitors of the mycobacterial transcriptional repressor EthR have previously been shown to act as boosters of the second-line antituberculosis drug ethionamide. Fragment-based drug discovery approaches have been used in the past to make highly potent EthR inhibitors with ethionamide boosting activity both in vitro and ex vivo. Herein, we report the development of fragment-sized EthR ligands with nanomolar min. effective concentration values for boosting the ethionamide activity in Mycobacterium tuberculosis whole-cell assays.

ACS Chemical Biology published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C7H13Br, Name: (2-Bromoethyl)cyclopentane.

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

Thompson, Andrew M. published the artcileBiarylmethoxy 2-nitroimidazooxazine antituberculosis agents: Effects of proximal ring substitution and linker reversal on metabolism and efficacy, Product Details of C7H5Br2F, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(18), 3804-3809, database is CAplus and MEDLINE.

Certain biaryl analogs of antitubercular drug PA-824 displayed enhanced in vivo efficacies yet retained some susceptibility towards oxidative metabolism; therefore, two new strategies were explored to address this. Ortho-substitution of the proximal aryl ring with larger electron-withdrawing substituents maintained or improved compound stability but reduced aerobic potency; however, fluoro and cyano were well tolerated. In vivo, only 2′- or 3′-fluoro mono-substitution preserved high efficacy against acute infection, although one example was twofold more effective than delamanid against chronic infection. Reversal of the 6-oxymethylene linkage also permitted high potency and improved stability towards human liver microsomes, albeit, in vivo results were inferior. These novel findings provide further insight into the preferred structural features for lead candidates in this important drug class.

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 C2H4ClNO, Product Details of C7H5Br2F.

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

Apsel, Beth published the artcileTargeted polypharmacology: discovery of dual inhibitors of tyrosine and phosphoinositide kinases, SDS of cas: 849062-12-0, the publication is Nature Chemical Biology (2008), 4(11), 691-699, database is CAplus and MEDLINE.

The clin. success of multitargeted kinase inhibitors has stimulated efforts to identify promiscuous drugs with optimal selectivity profiles. It remains unclear to what extent such drugs can be rationally designed, particularly for combinations of targets that are structurally divergent. Here we report the systematic discovery of mols. that potently inhibit both tyrosine kinases and phosphatidylinositol-3-OH kinases, two protein families that are among the most intensely pursued cancer drug targets. Through iterative chem. synthesis, X-ray crystallog. and kinome-level biochem. profiling, we identified compounds that inhibit a spectrum of new target combinations in these two families. Crystal structures revealed that the dual selectivity of these mols. is controlled by a hydrophobic pocket conserved in both enzyme classes and accessible through a rotatable bond in the drug skeleton. We show that compound I blocks the proliferation of tumor cells by direct inhibition of oncogenic tyrosine kinases and phosphatidylinositol-3-OH kinases. These mols. demonstrate the feasibility of accessing a chem. space that intersects two families of oncogenes.

Nature Chemical Biology 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 C7H8BBrO3, SDS of cas: 849062-12-0.

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

Padwa, Albert published the artcileSynthetic approaches toward the bi(2H-azirine) system, Category: bromides-buliding-blocks, the publication is Journal of Organic Chemistry (1979), 44(19), 3281-7, database is CAplus.

Three different approaches toward the synthesis of the bis(2H-azirine) system (I) were investigated. The 1st route is based on a modified Neber reaction in which the bis(trimethylhydrazonium) salt of 2,3-dimethyl-1,4-diphenyl-1,4-butanedione was treated with base. No indication of any bis(2H-azirine) could be detected in this reaction. In a 2nd approach, the reaction of 2-styryl-3-phenyl-2H-azirine with iodine azide was investigated. The major product isolated from this reaction was 1-phenyl-5-(1-azidocinnamyl)tetrazole. Subsequent studies with model systems showed that the reaction of IN₃ with 3-phenyl-2-substituted 2H-azirine gives azidotetrazoles in moderate yield. The reaction involves the addition of IN₃ across the CN double bond followed by ring opening of a transient iodoaziridine. Attack of azide on the incipient carbonium ion followed by electrocyclization of the azidoimine formed readily accommodates the formation of the tetrazole ring. The 3rd approach used for the synthesis of the bis(2H-azirine) system involved an attempt to dimerize 2-chloro-2H-azirines with activated metals or by electrolysis. 2-Chloro-2-methyl-2-phenyl-2H-azirine rearranges to the isomeric 2-chloro-3-methyl-2-phenyl-2H-azirine in solution This rearrangement is consistent with the intermediacy of an azacyclopropenyl ion chloride pair. All attempts at dimerization proved unsuccessful.

Journal of Organic Chemistry published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Category: bromides-buliding-blocks.

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

Paliwal, Khushboo S. published the artcileIonic Liquid Functionalized Chitosan Catalyst with Optimized Hydrophilic/Hydrophobic Structural Balance for Efficient CO₂ Fixation, Quality Control of 111-83-1, the publication is Asian Journal of Organic Chemistry (2022), 11(6), e202200121, database is CAplus.

In this work a series of chitosan-based catalysts with ranging hydrophobic/hydrophilic balance are successfully prepared by varying the ionic liquid and hydrocarbon chain length attached to chitosan. The chitosan modified with eight carbon units displayed efficient catalytic activity for the conversion of a wide range of epoxides to their corresponding cyclic carbonates under 1 atm pressure of carbon dioxide without cocatalyst and solvent. The optimized catalyst was able to convert even diepoxides and sterically bulky epoxides like t-Bu glycidyl ether to their corresponding cyclic carbonates. This study provides an insight into catalyst designing based on possible mol. interaction between reactants and active sites of the catalyst.

Asian Journal of Organic Chemistry published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Quality Control of 111-83-1.

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

Scott, James S. published the artcileUse of Small-Molecule Crystal Structures To Address Solubility in a Novel Series of G Protein Coupled Receptor 119 Agonists: Optimization of a Lead and in Vivo Evaluation, HPLC of Formula: 76283-09-5, the publication is Journal of Medicinal Chemistry (2012), 55(11), 5361-5379, database is CAplus and MEDLINE.

G protein coupled receptor 119 (GPR119) is viewed as an attractive target for the treatment of type 2 diabetes and other elements of the metabolic syndrome. During a program toward discovering agonists of GPR119, we herein describe optimization of an initial lead compound, 2, into a development candidate, 42. A key challenge in this program of work was the insolubility of the lead compound Small-mol. crystallog. was utilized to understand the intermol. interactions in the solid state and resulted in a switch from an aryl sulfone to a 3-cyanopyridyl motif. The compound was shown to be effective in wild-type but not knockout animals, confirming that the biol. effects were due to GPR119 agonism.

Journal of Medicinal Chemistry 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 C14H18BClO4, HPLC of Formula: 76283-09-5.

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

Chatalova-Sazepin, Claire published the artcileXenon Difluoride Mediated Fluorodecarboxylations for the Syntheses of Di- and Trifluoromethoxyarenes, Safety of Ethylbromofluoroacetate, the publication is Organic Letters (2016), 18(18), 4570-4573, database is CAplus and MEDLINE.

XeF₂ is demonstrated to be a more proficient fluorine-transfer reagent than either NFSI or Selectfluor in fluorodecarboxylations of both mono- and difluoroaryloxy acetic acid derivatives This method efficiently converts a wide range of neutral and electron-poor substrates to afford the desired di- and trifluoromethyl aryl ethers in good to excellent yields. The purifications are facile, and the reaction times are less than 5 min, which makes these fluorodecarboxylations promising for future PET-imaging applications.

Organic Letters published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Safety of Ethylbromofluoroacetate.

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