Chlorides-buliding-blocks

Schrittwieser, Joerg H. published the artcileBiocatalytic Cascade for the Synthesis of Enantiopure β-Azidoalcohols and β-Hydroxynitriles, HPLC of Formula: 5034-06-0, the publication is European Journal of Organic Chemistry (2009), 2293-2298, database is CAplus.

A three-step, two-enzyme, one-pot reaction sequence starting from prochiral α-chloroketones leading to enantiopure β-azidoalcs. and β-hydroxynitriles was described. Asym. bioreduction of α-chloroketones by hydrogen transfer catalyzed by an alc. dehydrogenase (ADH) established the stereogenic center in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalyzed ring closure to the epoxide and nucleophilic ring opening with azide, N₃^–, or cyanide, CN^–, both catalyzed by a nonselective halohydrin dehalogenase (Hhe), proceeded with full retention of configuration to give enantiopure β-azidoalcs. and β-hydroxynitriles, resp. Both enantiomers of various optically pure β-azidoalcs. and β-hydroxynitriles were synthesized. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009).

European Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, HPLC of Formula: 5034-06-0.

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

Coutrot, Philippe published the artcileSynthesis of diethyl 1,1-dichloroalkane- and 1-chloroalkanephosphonates, Computed Properties of 866-23-9, the publication is Synthesis (1977), 615-17, database is CAplus.

RCCl2P(O)(OEt)2 (I, R = Me, Et, Pr, Bu, CH2:CHCH2, MeCH:CHCH2, MeOCH2) and RR1CClP(O)(OEt)2 (II, R = Me, Et, Pr, Bu; R1 = H, Me, Et, Bu, CH2:CHCH2, Cl(CH2)3) (11 compounds) were prepared in 42-81 and 66-89% yields resp. Thus, alkylation of (EtO)2P(O)CCl2Li with RBr in presence of PO(NMe2)3 at -80° gave I. Lithiation of I followed by alkylation with R1X (X = Br, iodo) gave II.

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, Computed Properties of 866-23-9.

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

Hunziker, F. published the artcileChemistry and pharmacology of dibenzo[b,e][1,4]diazepine derivatives with basic substituents in position 10, Quality Control of 60091-87-4, the publication is Arzneimittel-Forschung (1963), 324-8, database is CAplus and MEDLINE.

A series of I derivatives was prepared according to Clemo, et al. (CA 19, 293) and Burton and Gibson (CA 19, 987) by an Ullmann-synthesis from o-bromonitrobenzenes and free anthranilic acid derivatives in presence of K₂CO₃ and catalytic amounts of Cu in a higher alcohol as solvent. The N-methylated anthranilic acids gave lower yields (50-60%) than the corresponding primary amines. The esters of I were best obtained via the acid chlorides. Thus, the following I derivatives were prepared (R¹, R², R³, and m.p. given): H, 4-Me, H, 213-15°; H, 4-Me, Et, 99-100°; Me, 4-Me, H, 140-1°; H, 4-Cl, H, 245-8°; H, 4-Cl, Et, 134-6°; Me, 4-Cl, H, 139-42°; H, 4-CF₃, H, 225-6°; H, 4-CF₃, Me, 147-8°; Me, 4-CF₃, H, 154-6°; H, 4-OMe, H, 228-30°; H, OMe, Et, 104°; Me, 4-OMe, H, 164-6°; H, 5-Cl, Me, 157-8°; H, 5-Cl, Et, 127-8°; Me, 5-Cl, H, 160°; Me, 5-Cl, Me, 92-3°; H, 5-OMe, Me, 149°; H, 5-SMe, Et, 187-8°; Me, 5-SMe, Me, 102-3°; H, 6-Cl, Me, 119-20°; H, 5′-Cl, Et, 106-7°; H, 5′-OMe, H, 235-7°; H, 4′-Cl, H, 232-5°; H, 4′-Cl, Me, 138°; H, 4′-OMe, H, 240°; Me, 4′-OMe, H, 168-72°. To a cooled solution of 5.9 g. K in 110 ml. tert-BuOH was added under stirring 12 g. MeSH. At 20°, a solution of 40.3 g. I (R¹ = R³ = Me, R² = 5-Cl) in 300 ml. HCONMe₂ was added. After 2 hrs. stirring at 80°, evaporation to dryness in vacuo, distribution between benzene and NaHCO₃ solution, evaporation of the benzene, and crystallization from Et₂O/petr. ether gave 40 g. I (R¹ = R³ = Me, R² = 5-SMe), m. 102-3°. To 135.6 g. I (R¹ = R³ = H, R² = 5-Cl) 10.3, suspended in 1.8 l. 2N aqueous NH₃ was added within 3 hrs. 266 g. Na₂S₂O₄. The mixture was heated to 80° till solution was complete. Charcoal treatment, acidification to pH 4.5 with AcOH, addition of NaCl, and work-up gave 121.3 g. II (R¹ = R³ = H, R² = 5-Cl), m. 208-5° (decomposition) (MeOH-H₂O). Similarly prepared were the II derivatives (R¹, R², R³, m.p. given): H, 4-Me, H, 213-15°; Me, 4-Me, H, 144-6°; H, 4-Cl, H, 200-5°; Me, 4-Cl, H, 155°; H, 4-CF₃, H, 214-15°; Me, 4-CF₃, H, 160°; H, 4-OMe, H, 200°; Me, 4-OMe, H, 132-4°; H, 5-Cl, Me, 117-18°; Me, 5-Cl, H, 155°; H, 5-OMe, H, 178-9°; H, 5-SMe, H, 170-2°; H, 6-Cl, Me, 135-9°; H, 5′-Cl, H, 175-7°; H, 5′-OMe, H, 182-4°; H, 4′-Cl, H, 197-8°. II (R¹ = R³ = H, R² = 5-Cl) (121.3 g.) was refluxed in 3 l. xylene 40 hrs. under continuous removal of H₂O. After distillation of the solvent and vapor distillation for removal of impurities, the residue was made alkaline with dilute NH₃, filtered, treated with charcoal, and crystallized from Me₂CO-H₂O to give 71.3 g. III (R¹ = H, R² = 7-Cl), m. 253-4°. The same compound was also obtained by refluxing of 2.5 g. II (R¹ = H, R² = 5-Cl, R³ = Me) with 0.39 g. NaNH₂ in 20 ml. dioxane, dilution with H₂O, and filtration in 83% yield. Similarly prepared were the following III derivatives (R¹, R², m.p. given): H, 2-Cl, 259-60°; H, 2-OMe, 220-1°; Me, 2-OMe, 200-12°; H, 3-Cl, 271°; H, 3-OMe, 232-3°; H, 3-Me, 267-9°; H, 6-Cl, 244-6°; Me, 7-Cl, 226-7°; H, 7-OMe, 239-40°; H, 7-SMe, 211-12°; Me, 7-SMe, 225-6°; H, 8-Cl, 231-2°; Me, 8-Cl, 214-15°; H, 8-Me, 194-5°; Me, 8-Me, 228-9°; H, 8-CF₃, 176-7°; Me, 8-CF₃, 239-40°; H, 8-OMe, 174-6°; Me, 8-OMe, 221-3°. III (R¹ = H, R² = 7-Cl) (52.5 g.) was refluxed 1 hr. with 9.2 g. NaNH₂ in 350 ml. dioxane, then 29 g. ClCH₂CH₂NMe₂ in 50 ml. benzene was added and the mixture refluxed 16 hrs. Concentration in vacuo, distribution between benzene/H₂O, extraction of the benzene with diluted HCl, alkalinization of the extract with NH₃, extraction with CHCl₃, evaporation of the solvent, and crystallization from Me₂CO/Et₂O gave 50.8 g. IV (R¹ = H, R² = 7-Cl), m. 165-6°, _ε230 32,740 (EtOH); hydrochloride m. 225-33° (EtOH-Et₂O). The same compound was obtained by refluxing 11.4 g. II (R¹ = H, R² = 5-Cl, R³ = Me) 90 min. with 1.8 g. NaNH₂ in 90 ml. dioxane, then adding 6 g. ClCH₂CH₂NMe₂ in 20 ml. benzene, and refluxing 15 hrs. (and usual work-up) in 56% yield. Similarly prepared were the following IV derivatives (R¹ R², m.p. free base, m.p. hydrochloride, L.D.₅₉ mg./kg. mouse per os given): H, H, 112-14°, -, 705; Me, H, 116-17°, 234-40°, 215; H, 2-Cl, 172-3°, -, 175; Me, 2-OMe, -, 205-10°, 900; H, 3-Cl, 159-60°, -, 305; H, 3-OMe, 141-3°, -, 150; H, 6-Cl, 122-3°, -, 260; H, 7-Cl, 165-6°, 225-33°, 330; Me, 7-Cl, -, 247-53°, 500; H, 7-OMe, 152-3°, -, 220; H, 7-SMe, 126-9°, -, 345; Me, 7-SMe, -, 205-7°, 520; H, 8-Cl, 140-5°, -, -; Me, 8-Cl, -, 240-5°, 500; H, 8-OMe, 126-7°, -, 220; H, 8-CF₃, 115-18°, -, 150; Me, 8-CF₈, -, 222-6°, 240; H, 8-Me, 137-8°, -, 127; Me, 8-Me, -, 214-17°, 100. Also prepared were the V derivatives (X, m.p., D.L.₅₀ mg./kg. mouse per os given): 2-pyrrolidinoethyl, 159-60°, 700; 2-piperidinoethyl, 187-9°, 700; 2-morpholinoethyl, 220-2°, >2500; CH₂CHMeNMe₂, 197-9°, 320; (CH₂)₃NMe₂, 137-9°, 1000. Reduction of the corresponding oxo derivatives with LiAlH₄ in tetrahydrofuran gave the VI derivatives (R¹, R², m.p., L.D.₅₀ mg./kg. mouse per os given): H, H, (maleate m. 100°), 600; Me, H, – (maleate m. 149-51°), 760; H, Cl, 87-9°, 275. IV (R¹ = H, R² = 2-Cl) (20 g.) was refluxed 24 hrs. in 200 ml. 5N HCl. Concentration in vacuo, addition of NaOH, and isolation of the resulting base gave 14.8 g. VII, b_8.97 130-8°. Acetylation with Ac₂O in pyridine gave VIII, m. 109-11°. To prove the structure, VIII was also synthesized independently. Thus, IX was acetylated to give X, m. 89-90° (Et₂O-petr. ether). X (31 g.) was alkylated with 4 g. NaNH₂ and 9.5 g. ClCH₂CH₂NMe₂ in 150 ml. dioxane to give after usual work-up 31.5 g. VIII. To test the influence of the N bridge on the pharmacol. properties, XI was prepared by refluxing 11.7 g. phenanthridone with 2.95 g. NaNH₂ in 120 ml. dioxane for 2 hrs. Addition of 7 g. ClCH₂CH₂NMe₂ in 50 ml. dioxane during 4 hrs., refluxing for 10 hrs, and normal work-up gave XI; hydrochloride m. 268-70° (MeOH-Et₂O). The XII derivatives were also prepared (X, m.p., L.D.₅₀ mg./kg. mouse per os given): S, 268-71° (hydrochloride) 870; SO₂, 113-23°, 620; O, 230-3° (hydrochloride), 500. The influence of the chem. constitution on the pharmacological activity was studied. A heterocyclic bridge in position 5 is indispensable for activity; derivatives of benzanilide and phenanthridone having basic substituents are inactive. An unsubstituted NH-group in position 5 has a more favorable effect than the Me-substituted N and is superior in activity to other hetero-bridges such as SO₂, S, and O. Compounds with substituents in position 7 show greater activity than the unsubstituted compound A carbonyl group in position 11 is essential for activity, the corresponding VI derivatives, although closely related to known antihistamines of the benzylaniline group are practically inactive in vivo. In agreement with other classes of antihistamines, the (CH₂)₂NMe₂ and (CH₂)₃NMe₂ groups are the most effective basic substituents. IV (R¹ = H, R² = 7-Cl) and the corresponding 7-SMe derivative belong to the most potent antihistaminics of today.

Arzneimittel-Forschung 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, Quality Control of 60091-87-4.

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

Hovlid, Marisa L. published the artcileEncapsidated Atom-Transfer Radical Polymerization in Qβ Virus-like Nanoparticles, Safety of 2-Chlorotrityl chloride, the publication is ACS Nano (2014), 8(8), 8003-8014, database is CAplus and MEDLINE.

Virus-like particles (VLPs) are unique macromol. structures that hold great promise in biomedical and biomaterial applications. The interior of the 30 nm-diameter Qβ VLP was functionalized by a three-step process: (1) hydrolytic removal of endogenously packaged RNA, (2) covalent attachment of initiator mols. to unnatural amino acid residues located on the interior capsid surface, and (3) atom-transfer radical polymerization of tertiary amine-bearing methacrylate monomers. The resulting polymer-containing particles were moderately expanded in size; however, biotin-derivatized polymer strands were only very weakly accessible to avidin, suggesting that most of the polymer was confined within the protein shell. The polymer-containing particles were also found to exhibit phys. and chem. properties characteristic of pos. charged nanostructures, including the ability to easily enter mammalian cells and deliver functional small interfering RNA.

ACS Nano published new progress about 42074-68-0. 42074-68-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 2-Chlorotrityl chloride, and the molecular formula is C19H14Cl2, Safety of 2-Chlorotrityl chloride.

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

Mantell, Mark A. published the artcileS_NAr and C-H Amination of Electron Rich Arenes with Pyridine as a Nucleophile Using Photoredox Catalysis, Synthetic Route of 637-07-0, the publication is Organic Letters (2021), 23(13), 5213-5217, database is CAplus and MEDLINE.

The development of two photocatalytic methods for the pyridination of electron rich arenes was described. First, an SNAr-type reaction between aryl halides and pyridine was developed and optimized. This transformation affords selective substitution of C(sp²)-halogen over C(sp²)-OR bonds to afford arylpyridinium products under anaerobic conditions. Under complementary aerobic conditions, analogous substrates were shown to undergo oxidative C(sp²)-H pyridination.

Organic Letters published new progress about 637-07-0. 637-07-0 belongs to chlorides-buliding-blocks, auxiliary class Inhibitor,Cell Cycle,PPAR, name is Ethyl 2-(4-chlorophenoxy)-2-methylpropanoate, and the molecular formula is C12H15ClO3, Synthetic Route of 637-07-0.

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

Delzenne, Gerard A. published the artcilePhotosensitive polymers. I. Synthesis and properties of coumarin-modified polymers, Recommanded Product: Coumarin-6-sulfonyl chloride, the publication is Industrie Chimique Belge (1967), 32(Spec. No.), 373-8, database is CAplus.

Polymers containing intramol. cinnamic esters of the coumarin type were synthesized by treating a poly(hydroxy ether) or partially hydrolyzed poly(vinyl butyral) with 6-coumarincarbonyl chloride, 6-coumarinsulfonyl chloride, or 7-coumarinyl 3-(chlorocarbonyl)-benzenesulfonate. A coumarin-containing copolymer was obtained by copolymerization of Et acrylate and 7-(acryloyloxy)coumarin. The photodimerization of coumarin functions by formation of a cyclobutane structure was useful for imagewise insolubilization of polymers. The photosensitivity of these polymers was compared with the sensitivity of poly(vinyl cinnamate). There was a linear relationship between the light sensitivity of the polymers and the degree of coumarin substitution. The photosensitivity can be enhanced by the addition of sensitizers of the carbonyl type. The more powerful sensitizer seems to be p,p’-bis(dimethylamino)-benzophenone. The sensitization was attributed to a triplet-triplet energy transfer between the light-excited sensitizers and the coumarin units.

Industrie Chimique Belge published new progress about 10543-42-7. 10543-42-7 belongs to chlorides-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Chloride,Sulfonyl chlorides,Ester, name is Coumarin-6-sulfonyl chloride, and the molecular formula is C9H5ClO4S, Recommanded Product: Coumarin-6-sulfonyl chloride.

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

Karimi, Farhad published the artcilePalladium-mediated carboxylation of aryl halides (triflates) or benzyl halides using [¹³C]/[¹¹C]carbon monoxide with tetramethylammonium hydroxide or trimethylphenylammonium hydroxide, Safety of 3-Chloro-2,6-dimethoxybenzoic acid, the publication is Journal of the Chemical Society, Perkin Transactions 1 (2002), 2256-2259, database is CAplus.

[Carbonyl-¹¹C]carboxylic acids were synthesized using palladium-mediated reaction of [¹¹C]carbon monoxide with aryl halides/triflates and benzyl halides in combination with either tetramethylammonium hydroxide or trimethylphenylammonium hydroxide. The radiochem. yields were in the range 20-85%. In a typical experiment starting with 2.1 GBq[¹¹C]carbon monoxide, 0.6 GBq of HPLC-purified 1-[carbonyl-¹¹C]naphthoic acid was obtained within 25 min of the start of the carbonylation reaction (67% decay-corrected radiochem. yield). The specific radioactivity of [carbonyl-¹¹C]nicotinic acid was in the order of 750 GBq μmol^-1 using 10.0 μAh bombardment. [Carbonyl-¹³C]nicotinic acid was synthesized to verify the position of the labeling (δ 166.1) determined by ¹³C NMR.

Journal of the Chemical Society, Perkin Transactions 1 published new progress about 36335-47-4. 36335-47-4 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Ether, name is 3-Chloro-2,6-dimethoxybenzoic acid, and the molecular formula is C9H9ClO4, Safety of 3-Chloro-2,6-dimethoxybenzoic acid.

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

Braendstroem, Arne published the artcileTrimethyloxosulfonium chloride from the iodide through ion pair extraction, Recommanded Product: trimethyloxosulphonium chloride, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1974), 28(5), 590, database is CAplus.

Trimethyloxosulfonium chloride (I) was prepared from the iodide (II) by extraction with Ph-CH2N+Bu3Cl- (III) between CH2Cl2 and H2O. Thus, III in H2O was shaken with II in CH2Cl2 and the aqueous phase washed with CH2Cl2 and then evaporated to give I.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Recommanded Product: trimethyloxosulphonium chloride.

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

Liu, Kevin G. published the artcileIdentification of a series of PPARγ/δ dual agonists via solid-Phase parallel synthesis, Quality Control of 33697-81-3, the publication is Bioorganic & Medicinal Chemistry Letters (2001), 11(22), 2959-2962, database is CAplus and MEDLINE.

The authors have developed a general solid-phase synthesis for identification of PPAR (peroxisome proliferator-activated receptors) ligands. Synthesis of a 480-member library led to the identification of a potent PPARγ/δ dual agonist 23. Compound I showed good plasma exposure in rats and demonstrated antihyperglycemic and antihyperlipidemic efficacy in diabetic fatty Zucker rats. Compounds with PPARγ/δ dual activity may be useful in the treatment of metabolic syndrome X.

Bioorganic & Medicinal Chemistry Letters published new progress about 33697-81-3. 33697-81-3 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Phenol, name is 3-Chloro-4-hydroxyphenylacetic acid, and the molecular formula is C8H7ClO3, Quality Control of 33697-81-3.

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

Herbort, James H. published the artcileCationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-α-C-H Activation Leads to Z-Selective Coupling of Acrylates, Safety of Sodium chloro(tosyl)amide trihydrate, the publication is ACS Catalysis (2021), 11(15), 9605-9617, database is CAplus and MEDLINE.

Two intermol. hydroalkenylation reactions of 1,6-enynes N(R)(CH²CH=CH²)CH²CCR¹ (R = -N(Ts)-, -C(COOEt)₂-, -O-, -N(Boc)-; R¹ = 4-fluorophenyl, thiophen-3-yl, prop-1-en-2-yl, etc.) are presented which yield substituted 5-membered carbo- and -heterocycles I (R = -N(Ts)-, -C(COOEt)²-; R² = H, Me; R³ = H, Me, n-Bu). This reactivity is enabled by a cationic bis-diphenylphosphinopropane (DPPP)CoI species which forms a cobaltacyclopentene intermediate by oxidative cyclization of the enyne. This key species interacts with alkenes in distinct fashion, depending on the identity of the coupling partner to give regiodivergent products I. Simple alkenes undergo insertion reactions to furnish 1,3-dienes whereby one of the alkenes is tetrasubstituted. The acerylates R⁴CH=C(R⁵)C(O)OR⁶ (R⁴ = H, Me, OMe; R⁵ = H, Me; R⁶ = Me, Bn, Cy, t-Bu) were employed as coupling partners, and the site of intermol. C-C formation shifts from the alkyne to the alkene motif of the enyne, yielding Z-substituted-acrylate derivatives II. Computational studies provide support for the exptl. observations and show that the turnover-limiting steps in both reactions are the interactions of the alkenes with the cobaltacyclopentene intermediate via either a 1,2-insertion in the case of ethylene, or an unexpected α-C-H activation in the case of most acrylates. Thus, the H syn to the ester is activated through the coordination of the acrylate carbonyl to the cobaltacycle intermediate, which explains the uncommon Z-selectivity and regiodivergence. Variable time normalization anal. (VTNA) of the kinetic data reveals a dependence upon the concentration of cobalt, acrylate, and activator. A KIE of 2.1 was observed with Me methacrylate in sep. flask experiments, indicating that C-H cleavage is the turnover-limiting step in the catalytic cycle. Lastly, a Hammett study of aryl-substituted enynes yields a ρ value of -0.4, indicating that more electron-rich substituents accelerate the rate of the reaction.

ACS Catalysis 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, Safety of Sodium chloro(tosyl)amide trihydrate.

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