Month: December 2022

Zhang, He published the artcileA new protocol for synthesizing diarylmethanes using a benzyltitanium reagent as a nucleophile, Synthetic Route of 1160556-64-8, the publication is Journal of Chemical Research (2022), 46(2), 17475198221091941, database is CAplus.

The first palladium-catalyzed cross-coupling of various substituted benzyltitaniums with aryl triflates is presented for the synthesis of diarylmethanes in yields of up to 94% through highly selective C-O bond functionalization. The benzyltitaniums act as nucleophiles to realize the C(sp²)-C(sp³) cross-coupling with high efficiency within short reaction times. The reactions proceed at 60°C and show excellent functional group tolerance.

Journal of Chemical Research published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C19H22BNO5, Synthetic Route of 1160556-64-8.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Truffault, Robert published the artcileCondensation of halogenated derivatives of benzene with unsaturated hydrocarbons and with halogenated derivatives of the latter under the influence of concentrated sulfuric acid as catalyst, Quality Control of 20029-52-1, the publication is Compt. rend. (1938), 676-8, database is CAplus.

Halogenated benzenes condense with olefins, in the presence of concentrated H₂SO₄, in the same way that benzene does (cf. C. A. 30, 4154.8), yielding p-substituted halogenated benzenes. Cyclohexene and PhCl react to form p-chlorocyclohexylbenzene (I), b₁₆ 134°, d₂₀ 1.070, n_D²⁰ 1.5400; M. R. calculated 56.7, found 57.03. With PhBr the product is p-bromocyclohexylbenzene (II), b₁₆ 146°, d₁₉ 1.289, n_D²⁰ 1.5605; M. R., calculated 59.58, found 60.0. Oxidation of I with CrO₃ gave p-ClC₆H₄CO₂H, m. 236°. The Mg derivative of II reacts with CO₂ to form p-cyclohexylbenzoic acid, m. 200°. Allyl chloride (III) and PhCl react to form p-ClC₆H₄CHMeCHCl (IV), b₁₆ 117°, d₂₁ 1.185, n_D²⁰ 1.538; M. R., calculated 49.9, found 49.9. With PhBr the product is p-BrC₆H₄CHMeCH₂Cl (V), b₁₅ 134-5°, d₂₁ 1.416, n_D²¹ 1.558; M. R., calculated 52.8, found 53.2. The structures of IV and V were assigned on the basis of the structures established for the compounds prepared from C₆H₆ and III, loc. cit. Thus, H₂SO₄ may be used to prepare alkylbenzenes having halogenated side chains, which cannot be obtained in the Friedel-Crafts reaction.

Compt. rend. published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C16H18Br2ClN3O3, Quality Control of 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Sridhar, Arun Srikanth published the artcileEffect of stoichiometry on crosslinked epoxy resin characteristics: structural heterogeneities, topological defects, properties, free volume and segmental mobility, Category: quinuclidine, the publication is Soft Matter (2022), 18(12), 2354-2372, database is CAplus and MEDLINE.

Exptl. studies have shown that changes in stoichiometry (R, ratio of amine groups to epoxy groups) cause considerable variations in the properties of epoxy-amine systems. Rationales based on free volume concepts have been routinely used to address these variations in properties but have hardly been satisfactorily substantiated. Many of these rationales remain as unverified conjectures to date. Substantiating these rationales will certainly bolster our understanding of the structure-stoichiometry-property relationship, but is difficult, due to inherent challenges involved in unambiguously characterizing the structural heterogeneities induced by changes in stoichiometry (structural heterogeneities include compositional distribution in the functionality of monomers, non-uniform dispersion of elastic chains and topol. defects). The aim of the present work is to gain mol.-level insights into this relationship and to verify the rationales that rely on free volume concepts used for addressing the variations in properties with stoichiometry, with the help of all-atom mol. dynamics (MD) simulations. Five epoxy-amine systems with varying R ranging from 0.4 to 3, including the stoichiometric system (R = 1), were considered for these purposes. The properties of interest namely d., glass transition temperature (T_g) and thermal expansion coefficient in the rubbery state (α_rl) of these systems were predicted. The local structure, fractional free volume and segmental mobility of these systems were then subsequently characterized as a function of stoichiometry and the results were analyzed in detail. The role played by defects in properties and fractional free volume was then investigated. The results revealed significant insights into the compositional distribution of monomers with different functionalities as well as offered insights into the dispersion state and mobility of dangling chains, sols and elastic chains in the systems. Further, strong correlations were found between defect composition, fractional free volume at an elevated temperature (600 K) and thermomech. properties (T_g and α_rl) and it was established that the key mechanism underlying these correlations was the plasticization caused by defects. Anal. based on the rule of mixture models showed that these correlations were found to be in good agreement with the interpretations based on free volume concepts. The results also revealed a strong neg. correlation between fractional free volume at room temperature and defect composition, a phenomenon typically associated with the antiplasticization effect.

Soft Matter published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C2H2N4O2, Category: quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Neunhoeffer, Otto published the artcileTricyclohexylmethane series. III, SDS of cas: 20029-52-1, the publication is Justus Liebigs Annalen der Chemie (1936), 58-65, database is CAplus.

p-Cyclohexylphenylmagnesium iodide and 13 g. Me p-cyclohexylbenzoate give 3 g. p,p’-dicyclohexylbiphenyl (I), m. 205°; some p,p’-dicyclohexylbenzophenone, m. 135°; and as the principal fraction, tri-(p-cyclohexylphenyl)carbinol (II), m. 168°. The action of CO₂ upon the Grignard reagent gives p-cyclohexylbenzoic acid, I and II. II in concentrated H₂SO₄ gives an intensive red-yellow color; II does not react with the usual reagents to form a halogen derivative or a Me ether. The action of Ag upon tricyclohexylmethyl bromide is complete in about 3 months; the action of K-Na gives dicyclohexylcyclohexylidenemethane, m. 52°. The cyclohexyl residue does not favor the formation of free radicals.

Justus Liebigs Annalen der Chemie published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, SDS of cas: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Neunhoeffer, Otto published the artcileSynthesis and nitration of phenylcyclohexane, Safety of 4-Cyclohexylbenzoic acid, the publication is Journal fuer Praktische Chemie (Leipzig) (1932), 95-109, database is CAplus.

In the preparation of phenyleyelohexane (I) the yield is increased with an excess of C₆H₆; thus, 1 mol. cyclohexyl chloride and 3 mols. C₆H₆ give 0.55 mol. I and 0.18 mol. dicyclohexylbenzene (II), while 12 mols. C₆H₆ gives 0.8 mol. I and 0.08 mol. II. Degradation of I with O₃ gives cyclopentylacetic acid, characterized as the amide, m. 149°. Oxidation of II gives terephthalic acid. Nitration of I in Ac₂O with fuming HNO₃ gives a mixture of p- (III) and o-nitrocyclohexylbenzenes (IV), in the ratio 78: 22; III b_0.6 142°, m. 57°; IV b_0.5 113°, m. 45°. Electrolytic reduction of III gives quantitatively p-cyelohexylaniline; through the diazo reaction this gives 90% of pcyclohexyliodobenzene, b_0.5 117°, m. 4°, and 42% of nitrile, b_0.5 123°, m. 41°; hydrolysis gives p-cyclohexylbenzoic acid, m. 196°. Electrolytic reduction of IV gives o-cyclohexylaniline,b_0.6 106°.m.13°; Acderiv.,m.101°; Bzderiv.,m.154°. III is trimorphic, m. 54°, 56° and 57°.

Journal fuer Praktische Chemie (Leipzig) published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Safety of 4-Cyclohexylbenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Burgess, Laurence E. published the artcileThe preparation of immunosuppressant SR-31747, Product Details of C13H16O2, the publication is Synthetic Communications (1997), 27(12), 2181-2191, database is CAplus.

The preparation of immunosuppressant SR-31747 was described. Attempts to install a (Z)-allyl amine included Lindlar partial hydrogenation and vinyl stannane methodologies. Ultimately, the Wittig olefination of 3-chloro-4-cyclohexylbenzaldehyde with the ylide derived from β-aminoethyl phosphonium salt [i.e., [2-(cyclohexylethylamino)ethyl]triphenylphosphonium bromide] proved successful.

Synthetic Communications published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Product Details of C13H16O2.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Liu, Xin published the artcileHydrogenative depolymerization of silicon-modified polyureas, Recommanded Product: 4,4-Diaminodicyclohexyl methane, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(35), 5415-5418, database is CAplus and MEDLINE.

Silicon-modified polyureas were depolymerized by hydrogenation in the presence of Ru and Mn catalysts. Yields of up to 84% of the aliphatic diamine and 81% of silicon-containing diamine were achieved with a com. available PNP-Ru catalyst.

Chemical Communications (Cambridge, United Kingdom) published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Recommanded Product: 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Huang, Yao published the artcileHighly regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols enabled by a hydrogen-bonding assisting effect, Category: quinuclidine, the publication is Chemical Science (2022), 13(8), 2317-2323, database is CAplus and MEDLINE.

A ligand-controlled palladium-catalyzed highly regioselective and diastereodivergent aminomethylative annulation of dienyl alcs. with aminals were established, which allowed for producing either cis- or trans-disubstituted isochromans in good yields with complete regioselectivity and good to excellent diastereoselectivity. Moreover, the chiral cis-products were also obtained in good yields with up to 94% ee by using a chiral phosphinamide as the ligand. Mechanistic studies revealed that the hydroxyl group played a key role in facilitating the Pd-catalyzed Heck insertion regioselectively taking place across the internal C=C bond of conjugated dienes.

Chemical Science published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Category: quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Pei, Chunzhe published the artcileNi-Catalyzed Direct Carboxylation of Aryl C-H Bonds in Benzamides with CO₂, SDS of cas: 20029-52-1, the publication is Advanced Synthesis & Catalysis (2022), 364(3), 493-499, database is CAplus.

The direct carboxylation of inert aryl C-H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, authors report the Ni-catalyzed direct carboxylation of aryl C-H bonds in benzamides under 1 atm of CO₂ to afford various Me carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)-Ni(II)-Ni(I) catalytic cycle may be involved in this reaction.

Advanced Synthesis & Catalysis published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, SDS of cas: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Han, Jie published the artcileDesign and Synthesis of WJ-Phos, and Application in Cu-Catalyzed Enantioselective Boroacylation of 1,1-Disubstituted Allenes, Computed Properties of 20029-52-1, the publication is ACS Catalysis (2019), 9(8), 6890-6895, database is CAplus.

The highly enantioselective copper-catalyzed three-component boroacylation of 1,1-disubstituted allenes is reported by using a class of chiral ligands (WJ-Phos), delivering various functionalized organoboron compounds bearing an all-carbon stereocenter in moderate to good yields with high enantioselectivities. WJ-Phos is a ferrocene-derived chiral sulfinamide phosphine ligand and can be easily synthesized in gram-scale from readily available starting materials in short steps. The salient features of this reaction include moderate to good yields, high enantioselectivities, gram-scale synthesis, diverse synthetic transformations, and the development of a new chiral ligand.

ACS Catalysis published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Computed Properties of 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider