Month: December 2022

Walton, E. published the artcileNew analgesics. III. Homologs of amidone, isoamidone, and some related compounds, Product Details of C5H13Cl2N, the publication is Journal of the Chemical Society (1949), 648-55, database is CAplus.

cf. C.A. 42, 6814d. In view of the established value of amidone (Me₂NCHMeCH₂CPh₂COEt) as an analgesic, 4 series of related ketones have been prepared by condensing Ph₂CHCN with a Cl base and treating the resulting basic cyanides with Grignard reagents. In general, the analgesic and respiratory depression activities remain associated but not always in the same ratio, maximum activity being attained in the Et ketone in all 4 series. Data are given for the analgesic activity, respiratory depression activity, approx. LD₅₀ (i.v. injection into mice), and toxic concentration on isolated rabbit heart. MeCH(NMe₂)CH₂OH (32 g.) and 46 mL. SOCl₂ in 120 mL. CHCl₃, warmed 3 h., give 1-chloro-2-(dimethylamino)propane-HCl, deliquescent, m. 101-2°; heated 3 min. at 140-60°, it yields MeCHClCH₂NMe₂.HCl (not changed by heating at 190-200°), which results also from MeCH(OH)CH₂NMe₂ and SOCl₂. A mixture of 26 g. Me₂NCHMeCH₂CPh₂CN (I) and Me₂NCH₂CHMeCPh₂CN (II) (prepared by the German process, Rept. Number P.B. 981, Office of the Pub. Board, Wash., D. C., p. 84) crystallized from petr. ether (b. 60-80°), gives 13.5 g. I, m. 90-1° (HCl salt, m. 181-3°; HBr salt, m. 175°; HI salt, cream, m. 203-4°; nitrate, m. 168-70° (decomposition); methiodide, m. 238-46°); the oil from the mother liquor of I, treated with 40% HBr, gives 14 g. of the HBr salt, m. 223-4°, of II, m. 68-9°; HCl salt, m. 224-5°; HI salt, m. 212-13°; nitrate, m. 178° (decomposition); H D-tartrate, m. 88-98°; methiodide, m. 235-45°. I (5 g.) in 20 mL. xylene and MeMgI (7.7 g. MeI), heated 2 h. on the steam bath (ether allowed to evaporate) and 2 h. on a sand bath, give 5-dimethylamino-3,3-diphenyl-2-hexanone, m. 72-3° (HCl salt, m. 185-7°; HBr salt, m. 193-5°; HI salt, m. 180-2°). Amidone (III) (m. 80-2°) yields a HI salt, m. 198-9°, a nitrate m. 108-10° (decomposition), and a methiodide, m. 168-70°. I and PrMgI give 7-dimethylamino-5,5-diphenyl-4-octanone which yields a nitrate, m. 95-7°, a HI salt, m. 155-7°, and a HBr salt, m. 87-9°. I and iso-PrMgBr give 6-dimethylamino-4,4-diphenyl-2-methyl-3-heptanone, b₄ 176-86° (nitrate, m. 116-18°). I and BuMgI yield 2-dimethylamino-4,4-diphenyl-5-nonanone, characterized as the HCl salt, m. 83-6°; HBr salt, m. 103-5°; HI salt, m. 140-3°, and nitrate, m. 77-8°. I and PhMgBr give the intermediate ketimine (C₂₅H₂₈N₂.HCl), m. 136-8°; refluxed 2 h. with 20% HBr, this yields the HBr salt, m. 181-3°, of Ph 3-dimethylamino-1,1-diphenylbutyl ketone; HCl salt, m. 197-8°. I and PhCH₂MgBr give 5-dimethylamino-1,3,3-triphenyl-2-hexanone-HCl, m. 236-7°; HBr salt, m. 243-4°. I (40 g.) and 21.6 g. D-tartaric acid in 430 mL. Me₂CO and 10 mL. H₂O, kept 24 h. at 0°, give 28 g. of the H D-tartrate, m. 109-12°, [α]_D²⁰ 16° (H₂O), of (-)-I, m. 99-101°, [α]_D²¹ -51° (EtOH); the Me₂CO mother liquors plus a little ether, kept 4 days at 0°, give 14 g. of the H D-tartrate, m. 66-70°, [α]_D²⁰ 5° (H₂O), of (+)-I, m. 101°, [α]_D²² 49° (EtOH); HBr salt, m. 216-18°, [α]_D²² 5 (EtOH), -4° (H₂O); nitrate, m. 169-71° (decomposition), [α]_D²⁰ 5° (EtOH), -6° (H₂O). (-)-I and EtMgBr give (-)-III, m. 99-101°, [α]_D²² -32° (EtOH); HBr salt, m. 234-5°, [α]_D²² -134° (EtOH); HCl salt, m. 241-2° (decomposition), [α]_D²¹ -130° (H₂O). (+)-III, m. 98-100°, [α]_D²⁰ 28° (EtOH); HI salt, m. 175-7° (decomposition); nitrate, m. 148° (decomposition), [α]_D¹⁹ 137° (EtOH). I (2 g.), 4 mL. concentrated H₂SO₄, and 4 mL. H₂O, refluxed 20 min., give 2.3 g. of the acid sulfate, m. 222-3°, of γ-dimethylamino-α,α-diphenylvaleric acid (IV), m. 198-9° (decomposition); HCl salt, m. 213-16°; the mother liquor yields the amide, m. 175-6° (HCl salt, m. 190-1°); Me ester, m. 60-5° [HCl salt, m. 166-8° (decomposition); HBr salt, m. 182° (decomposition)]; Et ester, an oil (HBr salt, m. 167-8°). I (5 g.), 0.7 g. NaNH₂, and 10 mL. PhMe, refluxed 6-7 h., give 2.5 g. I and 3-dimethylamino-1,1-diphenylbutane, whose HBr salt m. 159-60°; it results also on heating IV 15 min. at 200°; methiodide, m. 195-6°. IV (0.8 g.) and 0.5 mL. SOCl₂ in CHCl₃, warmed 4 h. on the steam bath, give 3,3-diphenyl-1,5-dimethyl-2-pyrrolidone, m. 122-3°. II and MeMgI in xylene, heated 1 h. on the steam bath and refluxed 1 h., give the ketimine (methiodide, C₂₁H₂₉N₂I, decompose 176-230°), which yields 5-dimethylamino-3,3-diphenyl-4-methyl-2-pentanone, m. 61-5° (HBr salt, m. 194-6°). II (16.6 g.) and EtMgBr give the ketimine, b₁ 94° (methiodide, m. 240°); refluxed 2.5 h. with 20% HBr, it yields 10.3 g. 6-dimethylamino-4,4-diphenyl-5-methyl-3-hexanone-HBr, m. 139-44°; HI salt, m. 206-8°; nitrate, m. 182-3° (decomposition); H D-tartrate, m. 150-4°. II (16.6 g.) and PrMgBr give 3.75 g. of the HCl salt, m. 80-100°, of 1-dimethylamino-3,3-diphenyl-2-methyl-4-heptanone, m. 100-1°. II and 5 mols. iso-PrMgBr give 6-dimethylamino-4,4-diphenyl-2,5-dimethyl-3-hexanone, whose HBr salt m. 81-5°. II and excess 48% HBr, heated 3.5 h. at 180°, give 3,3-diphenyl-1,4-dimethyl-2-pyrrolidone, m. 121-3°. Ph₂CHCN (67.2 g.), 22 g. Me₂N(CH₂)₂CN, and 6.8 g. NaNH₂ in 200 mL. C₆H₆ give 39 g. crude 3-dimethylamino-1,1-diphenylpropyl cyanide (V); HCl salt, m. 196-7°; HI salt, m. 221-3°. V (14 g.) gives 9 g. 5-dimethylamino-3,3-diphenyl-2-pentanone (HCl salt, m. 152-3°); EtMgBr gives 6-dimethylamino-4,4-diphenyl-3-hexanone (HCl salt, m. 171-2°); PrMgI gives 1-dimethylamino-3,3-diphenyl-4-heptanone (HI salt, m. 156-7°); iso-PrMgBr yields 6-dimethylamino-4,4-diphenyl-2-methyl-3-hexanone (HBr salt, m. 104-6°). 3-(1-Piperidyl)-1,1-diphenylpropyl cyanide (VI), m. 73-4° [HCl salt, m. 196-7°; HBr salt, m. 185-6°; HI salt, m. 152-3°; nitrate, m. 155° (decomposition)]. VI and MeMgI give 5-(1-piperidyl)-3,3-diphenyl-2-pentanone (HBr salt, m. 162-3°; HI salt, m. 158-9°); EtMgI yields 6-(1-piperidyl)-4,4-diphenyl-3-hexanone (HBr salt, m. 192-3°); PrMgI gives 1-(1-piperidyl)-3,3-diphenyl-4-heptanone (HCl salt, m. 158-60°; HI salt, m. 217-20°). VI and PhMgBr give Ph 3-(1-piperidyl)-1,1-diphenylpropyl ketone-HBr, m. 191-3°. VI (1.9 g.) and 3.6 mL. H₂SO₄, refluxed 30 min., give 0.5 g. α,α-diphenyl-1-piperidinebutyric acid, m. 230-5° (decomposition) (HCl salt, m. 236° (decomposition); H sulfate, m. 105-14°), and 0.6 g. of the amide, m. 178-9°; Me ester-HBr, with 2 mols. H₂O, m. 78-82°; Et ester-HBr, m. 194-6°. VI (2.3 g.), 0.9 g. NaNH₂, and 25 mL. C₆H₆, refluxed 3 h., give 3-(1-piperidyl)-1,1-diphenylpropane-HCl, m. 208-10°.

Journal of the Chemical Society published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C4H6O3, Product Details of C5H13Cl2N.

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

Shaykhutdinova, Polina published the artcileFurther Structural Modification of Sulfur-Stabilized Silicon Cations with Binaphthyl Backbones, Related Products of chlorides-buliding-blocks, the publication is Synthesis (2019), 51(10), 2221-2229, database is CAplus.

The synthesis and spectroscopic characterization of two novel cationic Si-S Lewis pairs with a chiral 4,4′-disubstituted binaphthyl silepine backbone are described. Both Lewis acids induce significant enantioselectivity in the model Diels-Alder reaction of cyclohexa-1,3-diene and chalcone but addnl. substitution of the binaphthyl backbone exerts a minimal effect on enantioinduction compared to previously reported Lewis acids. Another Si cation with a chiral spirocyclic backbone induces enantioselectivity in the same range but its synthesis is laborious.

Synthesis 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 C40H35N7O8, Related Products of chlorides-buliding-blocks.

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

Florvall, Lennart published the artcilePotential neuroleptic agents. 2,6-Dialkoxybenzamide derivatives with potent dopamine receptor blocking activities, Category: chlorides-buliding-blocks, the publication is Journal of Medicinal Chemistry (1982), 25(11), 1280-6, database is CAplus and MEDLINE.

Nineteen novel N-(2-pyrrolidinylmethyl)benzamides I (R = OMe, OEt, OCHMe₂, or Cl; R¹ and R² = H, Br, or Cl; R³ and R⁴ = H or Et) were synthesized and tested for dopamine receptor blockade in vivo by their ability to block the apomorphine syndrome in the rat. Several compounds were more potent than sulpiride as dopamine receptor blockers and displayed low liability to induce extrapyramidal side effects (catalepsy) in the rat. The blockade of dopamine receptor activity in vivo was mainly confined to the levorotatory isomers having the S absolute configuration. Structure-activity relationships are discussed.

Journal of Medicinal Chemistry 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, Category: chlorides-buliding-blocks.

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

Coote, Susannah C. published the artcileStereoselective aziridination of cyclic allylic alcohols using chloramine-T, Application In Synthesis of 7080-50-4, the publication is Organic & Biomolecular Chemistry (2008), 6(23), 4299-4314, database is CAplus and MEDLINE.

The stereoselective aziridination of a range of cyclic allylic alcs. using two different chloramine salts (4-MeC₆H₄SO₂NClNa, TsNClNa and Me₃CSO₂NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alc. and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, while complete cis-diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcs. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopent-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

Organic & Biomolecular 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, Application In Synthesis of 7080-50-4.

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

Barnes, Natalie G. published the artcileRapid access to Asp/Glu side-chain hydrazides as thioester precursors for peptide cyclization and glycosylation, HPLC of Formula: 42074-68-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(8), 1006-1009, database is CAplus and MEDLINE.

Head-to-side-chain macrocyclic peptides, and neoglycopeptides, were readily prepared by site-specific amidation of aspartic and glutamic acid side-chain hydrazides. Hydrazides, serving as latent thioesters, were introduced through regioselective opening of the corresponding N_α-Fmoc (Fmoc = 9-fluprenylmethoxycarbonyl) protected anhydride precursors.

Chemical Communications (Cambridge, United Kingdom) 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, HPLC of Formula: 42074-68-0.

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

Mangion, Ian K. published the artcileIridium-Catalyzed X-H Insertions of Sulfoxonium Ylides, Computed Properties of 5034-06-0, the publication is Organic Letters (2009), 11(16), 3566-3569, database is CAplus and MEDLINE.

The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, com. available iridium catalyst. This method has applications in both intra- and intermol. reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

Organic Letters 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, Computed Properties of 5034-06-0.

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

Wang, Dengjin published the artcileSynthesis of an anti-α-amino epoxide by one-carbon homologation of an α-amino ester: (2S,3S)-1,2-epoxy-3-(Boc-amino)-4-phenylbutane, SDS of cas: 5034-06-0, the publication is Organic Syntheses (2007), 58-67, database is CAplus.

The title compound was prepared by homologation of (S)-PhCH₂CH(NHBoc)CO₂C₆H₄NO₂-4 with Me₂S(O):CH₂, conversion to (S)-PhCH₂CH(NHBoc)CO₂CH₂Cl with HCl, and cyclization with LiAlH(OCMe₃)₃. Several other chloro ketones were also prepared

Organic Syntheses 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 C25H47NO8, SDS of cas: 5034-06-0.

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

Sardo, Carla published the artcileWhen Functionalization of PLA Surfaces Meets Thiol-Yne Photochemistry: Case Study with Antibacterial Polyaspartamide Derivatives, Formula: C7H16ClNO2, the publication is Biomacromolecules (2014), 15(11), 4351-4362, database is CAplus and MEDLINE.

In this work we wish to report on the covalent functionalization of polylactide (PLA) surfaces by photoradical thiol-yne to yield antibacterial surfaces. At first, hydrophilic and hydrophobic thiol fluorescent probes are synthesized and used to study and optimize the conditions of ligation on alkyne-PLA surfaces. In a second part, a new antibacterial polyaspartamide copolymer is covalently grafted. The covalent surface modification and the d. of surface functionalization are evaluated by SEC and XPS analyses. No degradation of PLA chains is observed, whereas covalent grafting is confirmed by the presence of S2p and N1s signals. Antiadherence and antibiofilm activities are assessed against four bacterial strains, including Gram-neg. and Gram-pos. bacteria. A strong activity is observed with adherence reduction factors superior to 99.98% and biofilm formation decreased by 80%. Finally, in vitro cytocompatibility tests of the antibacterial surfaces are performed with L929 murine fibroblasts and show cell viability without promoting proliferation.

Biomacromolecules published new progress about 6249-56-5. 6249-56-5 belongs to chlorides-buliding-blocks, auxiliary class Phase Transfer Catalyst,Inhibitor,Natural product, name is 3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride, and the molecular formula is C7H16ClNO2, Formula: C7H16ClNO2.

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

Voronin, E. F. published the artcileGeometric and mechano-sorption modification of fumed nanosilica in the gaseous dispersion media, Formula: C38H74Cl2N2O4, the publication is Fizika i Khimiya Tverdogo Tila (2019), 20(1), 22-26, database is CAplus.

Methods of geometric and solvate-stimulated mechano-sorption-activated modification of fumed nanosilica in gaseous dispersion media, were developed and used to prepare functionalyzed nanofillers for polymeric systems. Non-volatile high- and low-mol. weight compounds (such as polymers, organic bioactive compounds, organic and inorganic salts) can be used as modifiers of nanofillers.

Fizika i Khimiya Tverdogo Tila published new progress about 38146-42-8. 38146-42-8 belongs to chlorides-buliding-blocks, auxiliary class Achiral Phase-Transfer Catalysts, name is N1,N10-Bis(2-((2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoethyl)-N1,N1,N10,N10-tetramethyldecane-1,10-diaminium chloride, and the molecular formula is C8H14O4, Formula: C38H74Cl2N2O4.

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

Song, Geyang published the artcileGeneral Method for the Amination of Aryl Halides with Primary and Secondary Alkyl Amines via Nickel Photocatalysis, Product Details of C12H15ClO3, the publication is Journal of Organic Chemistry (2022), 87(15), 10285-10297, database is CAplus and MEDLINE.

It was reported that Ni(II)-bipyridine complex catalyzed efficient C-N coupling of aryl chlorides and bromides with various primary and secondary alkyl amines under direct excitation with light. Intramol. C-N coupling was also demonstrated. The feasibility and applicability of the protocol in organic synthesis was attested by more than 200 examples.

Journal of Organic Chemistry 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 C8H7NaO4S, Product Details of C12H15ClO3.

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