Tag: M.W=250-300

Uvarov, Vladimir M. published the artcileFirst study of rhodium(I) complexes with chiral sulfur-containing terpenoids as catalytic systems for ketone hydrosilylation, Application of ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2020), 195(5), 376-387, database is CAplus.

Using a “chiral pool” approach, a number of chiral thiolate and sulfide ligands based on natural terpenes and terpenoids have been synthesized in a few simple steps. Two new Rh-thiolate complexes with the formula [Rh(CO)₂(μ-SR)]₂ were obtained. The influence of these complexes and catalytic systems formed by combining the synthesized ligands with [Rh(CO)₂(μ-Cl)]₂ and [Rh(cod)(μ-Cl)]₂, on the reaction rate, chemoselectivity, stereoselectivity and formation of tetraphenyldisiloxane in Rh-catalyzed asym. hydrosilylation of acetophenone as a model reaction have been studied. Mechanistic aspects of formation of silyl enol ether as a side product in the presence of S-containing ligands are presented.

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C9H6N2O2, Application of ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Marvel, C. S. published the artcileVinyl polymers. X. Polymers of the α-haloacrylic acids and their derivatives, Safety of 2,3-Dibromopropionylchloride, the publication is Journal of the American Chemical Society (1940), 3495-8, database is CAplus.

cf. C. A. 34, 7863.8. Passing Cl into a mixture of 2265 g. tech. Me acrylate and 1 l. MeOH at a temperature below 40° for 5-6 h. gives 85% of the Me ester (I) of III, b₂₁ 72-5°; Br gives 85-8% of the Me ester (II) of IV, b₂₂ 96-8°. Refluxing 175 g. of I and 500 cc. 20% HCl for 5 h. and extracting with 3 100-cc. portions of CHCl₃ give a 65% yield of crude ClCH₂CHClCO₂H (III); II gives 72% of BrCH₂CHBrCO₂H (IV) on hydrolysis with 48% HBr. With SOCl₂ III gives 53% of the acid chloride (V), b₁₆ 52-4°, and IV gives 77% of the acid chloride (VI), b₁₈ 81-4°. With excess of the proper alc. (heating at 100° for 10 min.) V gives the following esters of III: sec-Bu, b₂₅ 65-6°, n_D²⁰ 1.4423, d₂₀²⁰ 1.150, 88%; cyclohexyl, b₂ 95-7°, n_D²⁰ 1.4752, 91%; β-chloroethyl, b₂₂ 123-6°, n_D²⁰ 1.4739. VI gives the esters of IV: sec-Bu, b₂₆ 130-5°, n_D²⁰ 1.4855, d₂₀²⁰ 130-2°, 89%; cyclohexyl, b₂ 130-2°, n_D²⁰ 1.5139, 93%. PhOH and C₅H₅N with V yield 41% of the Ph ester of III, b₁₈ 130-5°, n_D²⁰ 1.5262; VI gives 45.5% of the Ph ester of IV, b₂ 132-5°, n_D²⁰ 1.5598. The α-haloacrylates were prepared by heating about 0.07 mol of the above esters and 0.10 mol of quinoline, quinaldine or PhNEt₂ at 100° for 10 min. in a N atm. α-Chloroacrylic esters: Et, b₁₈ 51-3°, n_D²⁰ 1.4384, 81%; sec-Bu, b₂₃ 73-3.5°, n_D²⁰ 1.4360, 58%; cyclohexyl, b₂ 51-2°, n_D²⁰ 1.4735, 69%; Ph, b₈ 91-3°, n_D²⁰ 1.5808, 25%; β-chloroethyl, b₂₀ 94-6°, n_D²⁰ 1.4729, 45%. α-Bromoacrylic esters: sec-Bu, b₂₃ 80-2°, n_D²⁰ 1.4660, d₂₀²⁰ 1.303, 72%; cyclohexyl, b₄ 100-6°, n_D²⁰ 1.4954, 54%; Ph, b₂ 95-6°, n_D²⁰ 1.5480, 46%. These esters polymerize on standing at room temperature for 2-3 wk, on heating at 100° for 20-30 min., by the action of UV light for 6-8 h., in the presence of Bz₂O₂, etc. In bulk polymerization experiments clear, hard glassy products were obtained; the polymers precipitated from dioxane by ether or alc. are white powders. Poly-α-chloroacrylic esters: Et, decomposes 160-70°, n²⁵ 1.502; sec-Bu, decomposes 160-5°, n²⁵ 1.500; cyclohexyl, decomposes 210-35°, n²⁵ 1.532; Ph, decomposes 160-8°; β-chloroethyl, decomposes 230-40°, n²⁵ 1.533. α-Br derivatives: Et, decomposes 125-30°; sec-Bu, decomposes 150-60°, n²⁵ 1.542; cyclohexyl, decomposes 140-50°, n²⁵ 1.547; Ph, decomposes 175-85°, n²⁵ 1.612. CH₂:CClCO₂H (VII) results in 62% yield by adding dropwise 110 g. of I to 275 g. Ba(OH)₂.8H₂O and 500 cc. H₂O, stirring 2 h. and adding 62.5 g. concentrated H₂SO₄ in 125 cc. H₂O, extracting with 5 200-cc. portions of ether containing hydroquinone and crystallizing from petr. ether. CH₂:CBrCO₂H (VIII) similarly results in 70% yield from II. Illumination of 75 g. VII in 500 cc. anhydrous ether for 3 days gives 55 g. of the polymer (IX), m. about 300°; it is soluble in cold H₂O and forms clear, tough films. Addition of 0.1 g. Bz₂O₂ to 10 g. VII at 70° causes polymerization in 15 min. (5.5 g. of IX); boiling 10 g. IX with 50 cc. H₂O gives a gel, hardening to an easily pulverizable mass, which analyzes for C₃H₂O₂; it is apparently a cross-linked lactone with some HO groups. Dropwise addition of 25 g. of ClCH₂CHClCOCl to 25 g. of PhNEt₂ at 85° and 70-80 mm. gives 37% of the chloride, of VII, b₇₈ 45-8°, n_D²⁰ 1.4689; illumination in CCl₄ for 3 days gives 67% of the polymer, m. 210-25°; the film from 1 g. in 10 cc. H₂O resembles that of IX. The polymer of VIII is relatively unstable and loses HBr rapidly at room temperature ClCH₂CH₂COCl (50 g.) and 35 g. HOC₂H₄Cl give 62 g. (92%) of β-chloroethyl β-chloropropionate, b₂₀ 109-11°, n_D²⁰ 1.4600; treatment with quinoline at 150-60° for 20 min. gives 53% of β-chloroethyl acrylate, b₂₀ 64-6°, n_D²⁰ 1.4490; the polymer is a soft rubbery material which did not harden on longer illumination.

Journal of the American Chemical Society published new progress about 18791-02-1. 18791-02-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 2,3-Dibromopropionylchloride, and the molecular formula is C3H3Br2ClO, Safety of 2,3-Dibromopropionylchloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Capuano, Ben published the artcileSynthesis and preliminary pharmacological evaluation of 4′-arylmethyl analogues of clozapine. I. The effect of aromatic substituents, Formula: C13H9ClN2O4, the publication is Australian Journal of Chemistry (2002), 55(9), 565-576, database is CAplus.

As part of a research program to develop compounds with mixed dopamine D₄ and serotonin 5-HT_2A antagonist activity with potential for the treatment of schizophrenia, the preparation of 8-chloro-11-[4-(phenylmethyl)-1-piperazinyl]-5H-dibenzo[b,e][1,4]diazepine derivatives I (R = H, Br, Cl, F, Me, OMe, CF₃, OCF₃, etc.) based on a structural modification of the atypical antipsychotic clozapine was reported. Corresponding 8-chloro-11-[4-[(1H-indol-3-yl)methyl]-1-piperazinyl]-5H-dibenzo[b,e][1,4]diazepine derivatives, bioisosteric 8-chloro-11-[4-[(pyridinyl)methyl]-1-piperazinyl]-5H-dibenzo[b,e][1,4]diazepine derivatives, 4-[[4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)-1-piperazinyl]methyl]-1,2-benzenediol and 3-[[4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)-1-piperazinyl]methyl]-1H-indol-5-ol were also prepared The chem. synthesis, structural characterization and pharmacol. evaluation of a series 4′-arylmethyl analogs of clozapine are described. Preliminary receptor binding data are presented, examining primarily the electronic and positional effects of substituents on the introduced arylmethyl group, and secondarily the nature of the aryl ring.

Australian Journal of Chemistry published new progress about 60091-87-4. 60091-87-4 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Nitro Compound,Carboxylic acid,Amine,Benzene, name is 2-((4-Chloro-2-nitrophenyl)amino)benzoic acid, and the molecular formula is C13H9ClN2O4, Formula: C13H9ClN2O4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Nuti, Elisa published the artcileSugar-Based Arylsulfonamide Carboxylates as Selective and Water-Soluble Matrix Metalloproteinase-12 Inhibitors, Application of (4-((4-Chlorobenzyl)oxy)phenyl)boronic acid, the publication is ChemMedChem (2016), 11(15), 1626-1637, database is CAplus and MEDLINE.

Matrix metalloproteinase-12 (MMP-12) can be considered an attractive target to study selective inhibitors useful in the development of new therapies for lung and cardiovascular diseases. .In this study, a new series of arylsulfonamide carboxylates, with increased hydrophilicity resulting from conjugation with a β-N-acetyl-D-glucosamine moiety, were designed and synthesized as MMP-12 selective inhibitors. Their inhibitory activity was evaluated on human MMPs by using the fluorimetric assay, and a crystallog. anal. was performed to characterize their binding mode. Among these glycoconjugates, a nanomolar MMP-12 inhibitor with improved water solubility, compound I was identified.

ChemMedChem published new progress about 870778-91-9. 870778-91-9 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (4-((4-Chlorobenzyl)oxy)phenyl)boronic acid, and the molecular formula is C13H12BClO3, Application of (4-((4-Chlorobenzyl)oxy)phenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Xing, Siyang published the artcileDiastereoselective synthesis of cis-1,3-disubstituted isoindolines via a highly site-selective tandem cyclization reaction, Safety of Sodium chloro(tosyl)amide trihydrate, the publication is Organic Chemistry Frontiers (2018), 5(12), 1950-1956, database is CAplus.

A highly site-selective tandem reaction involving regioselective ring opening of aziridines and Michael addition of electron-deficient alkenes was described. O-atom nucleophiles, produced by the reaction of aldehydes and NHCs in open air, preferred to attack the less hindered aziridine carbons, followed by further intramol. aza-Michael addition to afford a series of cis-1,3-disubstituted isoindolines in good yields with good diastereoselectivities. High selectivities, high efficiency and mild conditions made this tandem reaction very suitable for the rapid construction of libraries of isoindoline compounds

Organic Chemistry Frontiers published new progress about 7080-50-4. 7080-50-4 belongs to chlorides-buliding-blocks, auxiliary class Halogenation Reagent,Inhibitor, name is Sodium chloro(tosyl)amide trihydrate, and the molecular formula is C10H17N3O2, Safety of Sodium chloro(tosyl)amide trihydrate.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

He, Xiaohui published the artcileIdentification of Potent and Selective RIPK2 Inhibitors for the Treatment of Inflammatory Diseases, Recommanded Product: 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, the publication is ACS Medicinal Chemistry Letters (2017), 8(10), 1048-1053, database is CAplus and MEDLINE.

NOD2 (nucleotide-binding oligomerization domain-containing protein 2) is an internal pattern recognition receptor that recognizes bacterial peptidoglycan and stimulates host immune responses. Dysfunction of NOD2 pathway has been associated with a number of autoinflammatory disorders. To date, direct inhibitors of NOD2 have not been described due to tech. challenges of targeting the oligomeric protein complex. Receptor interacting protein kinase 2 (RIPK2) is an intracellular serine/threonine/tyrosine kinase, a key signaling partner, and an obligate kinase for NOD2. As such, RIPK2 represents an attractive target to probe the pathol. roles of NOD2 pathway. To search for selective RIPK2 inhibitors, the authors employed virtual library screening (VLS) and structure based design that eventually led to a potent and selective RIPK2 inhibitor 8 (4-(7-ethoxy-6-(isopropylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-6-fluoropyridin-2-amine) with excellent oral bioavailability, which was used to evaluate the effects of inhibition of RIPK2 in various in vitro assays and ex vivo and in vivo pharmacodynamic models.

ACS Medicinal Chemistry Letters published new progress about 960388-56-1. 960388-56-1 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Phenol,Boronate Esters,Boronic Acids,Boronic acid and ester,Boronate Esters, name is 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, and the molecular formula is C12H16BClO3, Recommanded Product: 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Rubin, Heather published the artcileScalable Synthesis of N-Acylaziridines from N-Tosylaziridines, Name: Sodium chloro(tosyl)amide trihydrate, the publication is Journal of Organic Chemistry (2013), 78(17), 8865-8871, database is CAplus and MEDLINE.

N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaziridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochem. purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.

Journal of Organic Chemistry published new progress about 7080-50-4. 7080-50-4 belongs to chlorides-buliding-blocks, auxiliary class Halogenation Reagent,Inhibitor, name is Sodium chloro(tosyl)amide trihydrate, and the molecular formula is C7H13ClNNaO5S, Name: Sodium chloro(tosyl)amide trihydrate.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Harmse, Rozanne published the artcileActivities of 11-Azaartemisinin and N-Sulfonyl Derivatives against Asexual and Transmissible Malaria Parasites, Related Products of chlorides-buliding-blocks, the publication is ChemMedChem (2017), 12(24), 2086-2093, database is CAplus and MEDLINE.

Dihydroartemisinin (DHA), either used in its own right or as the active drug generated in vivo from the other artemisinins in current clin. use-artemether and artesunate-induces quiescence in ring-stage parasites of Plasmodium falciparum (Pf). This induction of quiescence is linked to artemisinin resistance. Thus, we have turned to structurally disparate artemisinins that are incapable of providing DHA on metabolism Accordingly, 11-azaartemisinin 5 and selected N-sulfonyl derivatives were screened against intraerythrocytic asexual stages of drug-sensitive Pf NF54 and drug-resistant K1 and W2 parasites. Most displayed appreciable activities against all three strains, with IC₅₀ values <10.5 nM. The p-trifluoromethylbenzenesulfonyl-11-azaartemisinin derivative 11 [(4′-trifluoromethyl)benzenesulfonylazaartemisinin] was the most active, with IC₅₀ values between 2 and 3 nM. The compounds were screened against Pf NF54 early and transmissible late intraerythrocytic-stage gametocytes using luciferase and parasite lactate dehydrogenase (pLDH) assays. The 2′-thienylsulfonyl derivative 16 (2′-thiophenesulfonylazaartemisinin) was notably active against late-stage (IV-V) gametocytes with an IC₅₀ value of 8.7 nm. All compounds were relatively nontoxic to human fetal lung WI-38 fibroblasts, showing selectivity indexes of >2000 toward asexual parasites. Overall, the readily accessible 11-azaartemisinin 5 and the sulfonyl derivatives 11 and 16 represent potential candidates for further development, in particular for transmission blocking of artemisinin-resistant parasites.

ChemMedChem published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Related Products of chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Slack, Eric D. published the artcileUnderstanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics, Synthetic Route of 929626-16-4, the publication is Organic Letters (2021), 23(5), 1561-1565, database is CAplus and MEDLINE.

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified using catalytic amounts of H₂O, alcs., etc., when B₂pin₂ was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]₂/dtbbpy or Me₄Phen.

Organic Letters published new progress about 929626-16-4. 929626-16-4 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronate Esters, name is 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C10H18O, Synthetic Route of 929626-16-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Grandin, Catherine published the artcileA practical synthesis of cycloalkylphosphonates from trichloromethylphosphonates, Application In Synthesis of 866-23-9, the publication is Synthesis (1995), 239-41, database is CAplus.

Cycloalkylophosphonates I (R = Et, CHMe₂, n = 1,2,3,4, X = H) with ring size varying from 4 to 6 were synthesized in good overall yields, in two steps from trichloromethylphosphonates and ω-dibromalkanes, via the corresponding α-trimethylsilyl cycloalkylphosphonates I (X = SiMe₃, R and n = same).

Synthesis published new progress about 866-23-9. 866-23-9 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyltrichloromethylphosphonate, and the molecular formula is C5H10Cl3O3P, Application In Synthesis of 866-23-9.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics