Tag: M.W=200-250

Bestman, HansJuergen published the artcileReactions with phosphinealkylenes. VII. Olefins and ketones by autoxidation of phosphinealkylenes, Quality Control of 594-81-0, the publication is Chemische Berichte (1963), 96(7), 1899-908, database is CAplus.

cf. CA 58, 13788g. Phosphinealkylenes of the type RCH:PPH₃ (R = alkyl) are oxidized by O to olefins and Ph₃PO. Phosphinealkylenes of the type RR’C:PPh₃ (I) yield with O the corresponding ketones. If the autoxidation of the I is interrupted after consumption of 1 O, olefins can also be formed by the Wittig reaction of the resulting ketone with unoxidized I. Ph₃P (26 g.) and 20 g. EtMeCHBr heated 18 hrs. at 100-20° in a sealed tube, and the powd. product boiled 2-3 times with C₆H₆ yielded 38 g. [iso-BuPPh₃]Br (II), m. 235-8° Ph₂P (13 g.) and 9.0 g. hexahydrobenzyl bromide heated 24 hrs. at 140-50° in a sealed tube, and the powd. product washed with pert. ether yielded 21 g. triphenylhexahydrobenzylphosphonium bromide (III), m. 225-8° (with softening from 200°). Ph₃P (26 g.) and 16 g. p-MeOC₆H₄CH₂Cl heated 1 hr. at 80-100°, and the powd. product boiled 2-3 times with C₆H₆ yielded 41 g. [p-MeOC₆H₄CH₂PPh₃]Cl (IV), m. 214-18° (CHCl₃-EtOAc). Ph₃P (26 g.) and 27 g. cyclohexyl bromide heated 60 hrs. at 140° in a sealed tube gave similarly 40 g. triphenylcyclohexylphosphonium bromide (V), m. 255-9° (CHCl₃-EtOAc). NaNH₂ (up to 25% excess) in dry NH₃ treated with the dry, powd. phosphonium salt, the NH₃ evaporated, the residue boiled about 10 min. with C_H6, MePh, Et₂O, tetrahydrofuran, etc., and the solution oxidized with O gave the corresponding oxidation products; method A. Na, K, or Li in 100 cc. absolute MeOH, EtOH, or tert-BuOH treated with an equivalent amount dry, powd. phosphonium salt gave a solution of phosphinealkylene which can be oxidized with O; method B. All operations up to the oxidation have to be performed under N or Ar. The oxidations with O were carried out in a special apparatus (described in detail) in which a measured amount O can be recirculated. [PhCH₂PPh₃]Br (18.0 g.) and 0.92 g. Na in 100 cc. absolute EtOH processed by method B, and the refluxing ylide solution treated 24 hrs. with 0 and poured into 100 cc. 10% HBr precipitated 1.46 g. trans-stilbene (VI), m. 121°; the filtrate evaporated, the residue extracted with Et₂O, the extract diluted with petr. ether, the precipitated Ph₃PO (10.3 g.) filtered off, and the filtrate distilled gave 0.84 g. cis-stilbene (VII), b₁₂ 140-2°, n²⁰_D 1.6189. Tricyclohexylbenzylphosphonium chloride (8.1 g.) treated with 0.46 g. Na in 50 cc. absolute EtOH by method B and oxidized 12 hrs. at reflux, and the mixture poured into 50 cc. 10% HBr gave 1.2 g. VI; the acidic mother liquor concentrated gave 1.2 g. unchanged phosphonium salt and 74% tricyclohexylphosphine oxide. [¹PhCH₂PPh₃]Cl treated with 0.6 g. Na and 70 cc. C₆H₆ by method A, the solution oxidized 5 hrs. at 80° (96% O consumption) and evaporated, and the residue dissolved in 30 cc. MeOH and poured into 20 cc. 10% HBr yielded 1.7 g. VI and only a small amount of VII; the mother liquor diluted with H_O precipitated 5.8 g. Ph₃PO. IV (12.5 g.), 1.2 g. Na, and 150 cc. dry C₆H₆ processed by method A, and the solution oxidized 1 hr. at room temperature (84% O consumption) yielded 1.4 g. trans-(MeOC_H4CH:)₂, m. 210-11° (MeOH-H₂O); the mother liquor evaporated and the residue triturated with petr. ether left 6.9 g. Ph₃PO; the petr. ether extract distilled yielded 0.70 g. cis-p-(MeOC₆H₄CH:)₂, b_0.1 140°, m. 35°. [EtPPh₃]Br (11.1 g.) treated by method A with 0.9 g. Na in 150 cc. dry Et₂O and oxidized 15 min. at 0% and the effluent gas (swept with N) passed into BrCHCl₃ yielded 2.7 g. (MeCHBr)₂, b₁₂ 58-62°; the Et₂O solution yielded 6.2 g. Ph₃PO₂. [PrPPh₃]Br (11.7 g.) treated by method A with 0.9 g. Na and 100 cc. MePh and oxidized 15 min. at 0° (100% O consumption) yielded 0.90 g. 3-hexene, b. 63-5°. [BuPPh₃]Br (24 g.) treated with 1.8 g. Na and 150 cc. dry tetrahydrofuran by method A and oxidized 0.5 hr. at room temperature (92% O consumption) gave 14.8 g. Ph₃PO and 2.6 g. cis- and trans-4-octene, b₇₁₀ 117-18°; dibromide b₁₀ 103°. III (22.0 g.), 1.8 g. Na, and 150 cc. C₆H₆ processed by method A and oxidized 25 min. at room temperature (100.% O consumption) yielded 11.0 g. Ph₃PO, 0.80 g. hexahydrobehzaldehyde, b₁₅ 50-3° (2,4-dinitrophenylhydrazone m. 111-13°), and 2.9 g. cis- and trans-1,2-dicyclohexylethylene. [iso-PrPPh₃]Br (VIII) (15.8 g.) treated with 0.7 g. Na and 100 cc. MePh by method A and oxidized 5 min. at room temperature (80% O consumption) and the mixture distilled into aqueous 2,4-(O₂N)₂C₆H₃NHNH₂ gave 2.2 g. 2,4-(O₂N)₂C₆H₃NHN:CMe₂, m. 126°; the distillation residue evaporated and the residue triturated with 50 cc. petr. ether yielded 2.6 g. Ph₃PO. VIII (15.2 g.) treated by method A with 1.3 g. Na in 200 cc. dry C₆H₆, 1/2 of the resulting solution oxidized with O, the O.removed with N, the remaining unoxidized reaction solution added, the mixture distilled, and the distillate treated with Br yielded 2.8 g. (Me₂CBr)₂, m. 168-71° (EtOH); the distillation residue gave 6.7 g. Ph₃PO. The same result was obtained when the oxidation was interrupted after the consumption of 1 equivalent O and the mixture was kept several hrs.; 53% yield. VIII (6.0 g.) processed with 0.5 g. Na and 100 cc. MePh by method A and oxidized 10 min. at room temperature (75% O consumption), and distilled into aqueous 2,4-(O₂N)₂C₆H₃NHNH₂.HCl yielded 2.1 g. 2,4-(O₂N)₂C₆H₃NHN:CEtMe, m. 116-17°; the residue gave 3.5 g. Ph₃PO. VIII (16.0 g.) treated by method A with 1.4 g. Na and 200 cc. dry C₆H₆, 1/2 of the resulting solution oxidized, purged with N, treated with the remaining unoxidized solution, refluxed under N until pale yellow, and evaporated, and the residue treated with 100 cc. Et₂O and cooled gave 9.6 g. Ph₃PO; the filtrate distilled yielded 1.3 g. (EtMeC:)₂, b. 95-8° [dibromide b₇₆₀ 147-50° (slight decomposition)]; the same results were obtained when the oxidation was interrupted after the consumption of 1 equivalent O; 50% yield. [MePhC:PPh₃]Br (8.9 g.) treated with 0.7 g. Na and 100 cc. dry C₆H₆ by method A and oxidized 15 min. at room temperature (98% O consumption) yielded 4.2 g. Ph₃PO; the filtrate evaporated, and the residue treated with EtOH and 2,4-(O₂N)₂C₆H₃NHNH₂ solution gave 4.1 g. 2,4-(O₂N)₂C₆H₃NHN:-CMePh, m. 248°. [Ph₂CHPPh₃]Br (7.6 g.) treated with 0.6 g. Na and 200 cc. dry C₆H₆ by method A and oxidized 8 hrs. at room temperature (95% O consumption), the C₆H₆ distilled, and the residue treated with 60 cc. petr. ether yielded 3.1 g. Ph₃PO; the filtrate evaporated and the residue treated with 2,4-(O₂N)2C₆H₃NH-NH₂.H₃PO₄ solution yielded 3.8 g. 2,4-(O₂N)2C₆H₃NHN:CPh₂, m. 238°. V (8.5 g.) treated with 0.7 g. Na and 100 cc. C₆H₆ by method A and oxidized 15 min. at room temperature (77% O consumption), and the mixture worked up in the same manner gave 3.6 g. cyclohexanone 2,4-dinitrophenylhydrazone, m. 158°.

Chemische Berichte 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, Quality Control of 594-81-0.

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

Wojcieszak, Marta published the artcileSurface activity and phytotoxicity of morpholinium herbicidal ionic liquids, Safety of 1-Bromododecane, the publication is Journal of Molecular Liquids (2022), 119750, database is CAplus.

The use of efficient synthesis methods to obtain novel herbicidal ionic liquids (HILs) with biol. activity is extremely important because it can eliminate certain neg. environmental impacts. The authors of this work succeeded in the experiment, which resulted in the synthesis of 18 novel ionic liquids with high yields. Furthermore, a number of physicochem. and biol. properties have been investigated, including surface activity, thermal anal., and phytotoxicity. In addition, it was proven that morpholinium ionic liquids with phenoxyacid anions were more effective against cress than HILs previously studied in the literature. To the best of our knowledge, this is the first report of surface-active ionic liquids with herbicidal anions where leaf surfaces were used for anal. An important aspect of this work was to compare the wettability of the surfaces of wheat leaves and weeds. Moreover, it was shown that using paraffin as a reference surface was not sufficient to describe the wetting properties of HILs. The research reported here proved that morpholinium ionic liquids were effective in wetting weed surfaces while they do not adversely affect wheat leaf surfaces. Our results could be significant for meeting the environmental challenges and agricultural demands of the future.

Journal of Molecular Liquids published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C11H14O4, Safety of 1-Bromododecane.

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

Sommer, Stefan published the artcileSolid-phase synthesis of [5.5]-spiroketals, Synthetic Route of 69361-41-7, the publication is Advanced Synthesis & Catalysis (2008), 350(11+12), 1736-1750, database is CAplus.

An efficient and reliable multi-step synthesis of 251 natural product-like [5.5]-spiroketals on solid supports has been developed. As central key step, a double intramol. hetero-Michael (DIHMA) reaction to alkynones was applied. The sequence allows for introduction of numerous substituents on the scaffold and for variation of stereochem. [5.5]-Spiroketals bearing an addnl. ketone were obtained in high overall yields. Further diversification was achieved by reduction of the ketone and reductive amination using polymer-supported borohydride, Grignard reaction and conversion to oxime derivatives in the solution phase.

Advanced Synthesis & Catalysis 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 C15H12O6, Synthetic Route of 69361-41-7.

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

Malysheva, S. F. published the artcileChemoselective Synthesis of Alkylphosphinic Acids from Red Phosphorus and Alkyl Bromides in the System KOH/H₂O/Toluene/Micellar Catalyst, COA of Formula: C12H25Br, the publication is Russian Journal of Organic Chemistry (2022), 58(2), 192-199, database is CAplus.

Alkylphosphinic acids, including long-chain ones, were synthesized in up to 76% yields from red P and n-AlkBr (Alk = C₄-C₁₄) under micellar catalysis conditions. The reaction proceeds efficiently and chemoselectively upon heating (85-90°, 6 h) in a KOH/H₂O/toluene/cetyltrimethylammonium bromide system.

Russian Journal of Organic Chemistry published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C12H25Br, COA of Formula: C12H25Br.

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

Kaur, Ramanjeet published the artcileA thermodynamic investigation of the effect of cationic structure on the self-aggregation behavior of Surface-Active ionic liquids in the presence of an amino acid, Application of 1-Bromododecane, the publication is Journal of Molecular Liquids (2022), 118904, database is CAplus.

A series of imidazolium-based ionic liquids (ILs) with varying side alkyl chain length at N3 position which includes [C12mim][Br], [C12eim][Br], and [C12bim][Br] have been synthesized and characterized by ¹H NMR. Then, their aggregation behavior in the presence of different concentrations of the amino acid L-Tryptophan (L-Trp) at different temperatures has been examined using conductometric, tensiometric, and UV-vis (absorption spectra) techniques. The critical micelle concentration (CMC) of ILs has been investigated in the absence and presence of amino acid to acquire a better understanding of the colloidal behavior of ILs in presence of amino acid as an external additive. The addition of amino acid is observed to reduce the CMC values of the ILs examined in an aqueous media. Likewise, applying a charged pseudo-phase model of micellization, the thermodn. parameters of micellization, such as a change in standard free energy (ΔGom), change in standard enthalpy (ΔHom), and change in standard entropy (ΔSom), have been scrutinized from the dependence of CMC on temperature The surface tension approach was also used to evaluate interfacial characteristics. It was discovered that increasing the length of the side chain increases surface activity. All of the estimated parameters were utilized to determine the electrostatic and hydrophobic contributions of IL to the formation of micellar aggregates.

Journal of Molecular Liquids published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C12H25Br, Application of 1-Bromododecane.

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

Sharma, Ravinder published the artcileVolumetric and acoustic properties of L-phenyl glycine and L-phenylalanine in aqueous solution of 1-dodecyl-3-methylimidazolium bromide [C₁₂mim] [Br], Recommanded Product: 1-Bromododecane, the publication is Journal of Molecular Liquids (2022), 119014, database is CAplus.

To study the mol. interactions between the ternary mixtures containing long chain imidazolium based ionic liquid as a common solvent with substituted amino acids L-Ph glycine and L-phenylalanine resp., densities and speed of sound have been measured at three different temperatures viz. T = 288.15 K, 298.15 K, 318.15 and 318.15 K under 0.1 MPa pressure. The d. and speed of sound data have been further utilized to calculate the apparent molar volume and apparent molar isentropic compression. From the data obtained, apparent molar volume (V_ϕ), partial molar volume (V⁰_ϕ), and standard partial molar volumes of transfer (ΔV⁰_ϕ). Pos. values of apparent molar volume indicate strong interactions. Also, partial molar isentropic compression of transfer (ΔK⁰_ϕ,S) and partial molar isentropic compression (K_ϕ,S) have been calculated from the sound of speed. Furthermore, structure making and structure breaking ability of solute have been discussed by evaluation of apparent molar expansivity, (ϕ⁰_E), Hepler′s constant values (∂/∂T)p. The obtained results have been discussed in terms of solvation behavior, structural changes and various interactions present in different ternary mixtures (1-dodecyl-3-methylimidazolium bromide + amino acids + water).

Journal of Molecular Liquids published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C18H34N4O5S, Recommanded Product: 1-Bromododecane.

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

Rastyanite, L. published the artcileSulfoalkylation of 1,2-dihydro-3,6-pyridazine- and 2,3-dihydro-1,4-phthalazinediones and their N-phenyl derivatives by 1,3-propanesultone and bromoalkanesulfonates, Related Products of bromides-buliding-blocks, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) (2002), 38(11), 1363-1367, database is CAplus.

When 1,2-dihydropyridazine-3,6-dione, 2,3-dihydrophthalazine-1,4-dione, 1-phenyl-1,2-dihydropyridazine-3,6-dione, and 2-phenyl-2,3-dihydrophthalazine-1,4-dione react with 1,3-propanesultone and bromoalkanesulfonates, depending on the nature of the sulfoalkylating agent in the case of 1,2-dihydropyridazine-3,6-dione and 2,3-dihydrophthalazine-1,4-dione, either N,O- or O,O’-disulfoalkylated compounds may be formed, while O-monosulfoalkylated reaction products may be formed in the case of the N-phenyl-substituted derivatives of the above-indicated azinediones.

Chemistry of Heterocyclic Compounds (New York, NY, United States)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, Related Products of bromides-buliding-blocks.

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

Laufer, Stefan published the artcileTowards the improvement of the synthesis of novel 4(5)-aryl-5(4)-heteroaryl-2-thio-substituted imidazoles and their p38 MAP kinase inhibitory activity, Computed Properties of 66197-72-6, the publication is Organic & Biomolecular Chemistry (2008), 6(3), 437-439, database is CAplus and MEDLINE.

A series of 2-alkylsulfanyl-4-(4-fluorophenyl)-5-(2-aminopyridin-4-yl)-substituted imidazoles was prepared and interaction possibilities of the 2-thioether moiety with phosphate/ribose-binding pockets of p38 MAP kinase were investigated. Introduction of the alkyl/benzyl amino function at the pyridine moiety was carried out via nucleophilic substitution or via palladium-catalyzed aryl-C-N bond formation.

Organic & Biomolecular Chemistry published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Computed Properties of 66197-72-6.

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

Yasu, Yusuke published the artcileSunlight-driven synthesis of γ-diketones via oxidative coupling of enamines with silyl enol ethers catalyzed by [Ru(bpy)₃]²⁺, Synthetic Route of 594-81-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2012), 48(43), 5355-5357, database is CAplus and MEDLINE.

A photosensitizer [Ru(bpy)₃]²⁺ catalyzes oxidative coupling reaction of enamines with silyl enol ethers under visible light irradiation by a Xe lamp or sunlight to produce γ-diketones. A 2e-oxidation process involved in this reaction is achieved by a combination of the photoexcited [Ru(bpy)₃]²⁺ species and duroquinone, a 2e-acceptor.

Chemical Communications (Cambridge, United Kingdom) 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 C65H82N2O18S2, Synthetic Route of 594-81-0.

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

Zhang, Liming published the artcileStereocontrolled Synthesis of Kelsoene by the Homo-Favorskii Rearrangement, Computed Properties of 69361-41-7, the publication is Organic Letters (2002), 4(21), 3755-3758, database is CAplus and MEDLINE.

(±)-Kelsoene (I) has been synthesized from 2,5-dihydroanisole in 16 steps in 12.5% overall yield. The key step involves a base-catalyzed reaction of γ-keto tosylate II, which effects a homo-Favorskii rearrangement to III (X¹ = H,H; X² = O) as well as the corresponding intramol. S_N2 product IV from the enolate of II. Ketone IV can efficiently be isomerized to cyclobutanone III (X¹ = O; X² = H,H) having the kelsoene carbon skeleton upon acid treatment.

Organic Letters 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 C3H5BN2O2, Computed Properties of 69361-41-7.

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