Category: 1949-41-3

Krollpfelffer, F. published the artcileRing closures in ¦Ã-arylbutyric acids to derivatives of l-ketotetrahydronaphthalene, Related Products of catalysis-chemistry, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 620-32, database is CAplus.

The ¦Ã-arylbutyric acids were prepared by letting the corresponding ¦Ã-keto acids and 10 parts amalgamated Zn stand at least 2-3 hrs., with frequent shaking, under just enough 30% HCl to cover the Zn and then boiling vigorously 6-10 hrs. Although attempts to convert these acids into 1-keto-1,2,3,4-tetrahydronaphthalene (I) derivatives by direct elimination of H₂O between the side chain and the nucleus by means of concd, H₂SO₄ were not successful in all cases, it may be said in general that their tendency to undergo such a condensation is quite pronounced. PhCH₂CH₂CH₂C0₂H (obtained in 80% yield), heated 3 hrs. on the H₂O bath with 5 parts concentrated H₂SO₄ gives 50% I, b₁₃ 127¡ã. From 15 g. p-MeC₆H₄(CH₂)₃CO₂H (obtained in 80% yield) is obtained 9 g. of the 7-Me derivative of I, m. 32.5-3.5¡ã; semicarbazone, m. 224-5¡ã. The ketone (5 g.), reduced by Clemmensen’s method, gives 2 g. 2-methyl-5,6,7,8-tetrahydronaphthalene, b. 224-6¡ã, and with Br in CS₂ yields the 7-methyl-2-bromo derivative of I, m. 80.5¡ã, which produces severe burns on the skin and 9 g. of which, boiled 1 hr. with 50 g. PhNEt₂, regenerates about 1 g. of the Br-free ketone and yields 2 g. 7-methyl-I-naphthol, b₁₂. 158-9¡ã, m. 109¡ã, couples with diazotized P-O₂NC₆H₄NH₂ in alk. solution to a blue dye changing to red with acids. p- EtC₆H₄COCH₂CH₂CO₂H, obtained in 70 g. yield from 60 g. succinic anhydride and 100 g. PhEt with AlCl₃ in C₆H₆, m. 98-9¡ã. ¦Ã-p-Ethylphenylbutyric acid, m. 69-70¡ã, gives 50-5% of the 7-Et derivative of I, b₁₂ 152-3¡ã, slowly becomes brown-red in the air; semicarbazone, m. 223-5¡ã. Reduction of the ketone gives 2-ethyl-5,6,7,8-tetrahydronaph- thalene, b. 245-6¡ã. 2,4-Me₂C₆H₃COCH₂CH₂CO₂H, m. 111-2¡ã; the Me₂C₆H₃(CH₂)₃– CO₂H, m. 71¡ã, gives 10-5 % of the 5,7-Me₂ derivative of I, m. 49-50¡ã, the small yield being due to sulfonation of the xylylbutyric acid. The ketone, which b₁₄ 180-2¡ã, is obtained in 40% yield from Me₂C₆H₃COCl heated in vacuo at 150¡ã until the evolution of HCl ceases; semicarbazone, m. 234-5¡ã. ar-I,3-Dimethyltetralin (2.5 g. from 5 g. of the ketone with amalgamated Zn and HCl), b. 250-2¡ã. ¦Â-2-Tetroylpropionic acid (60 g. from 50 g. succinic anhydride and 100 g. tetralin with AlCl₃ in C₆H₆), m. 121-2¡ã. ¦Â-2-Tetralyl- butyric acid, m. 49-50¡ã, gives 75% 1-ketooctahydroanthracene (“octhracenone,” Schroeter, C. A. 15, 525), b₁₃ 202¡ã, m. 46-7¡ã; semicarbazone, m. 252-3¡ã; 2-Br derivative, m. 110¡ã, produces severe burns on the skin and with PhNEt₂ in part regenerates the Br-free ketone and in part forms 5,6,7,8-tetrahydro-I-anthrol, m. 124¡ã, becomes brown in the air, couples with diazotized P-O₂NC₆H₄NH₂ to a violet dye which is not fast to acids. ¦Â-¦Á’- Naphthoylisosuccinic acid, from CH₂(CO₂Et)₂ refluxed in C₆H₆ with Na and then with ¦Á-C₁₀H₇COCH₂Br, decomposes 158¡ã, with loss of CO₂, 10 g. giving 5 g. of ¦Â-¦Á’-naphthoylpropionic acid, m. 131-2¡ã. ¦Ã-p-Methoxyphenylbutyric acid, m. 59-60¡ã, gives with H₂SO₄ only an easily soluble SO₃H acid, but vacuum distillation of its chloride gives the 7-MeO derivative of I, m. 60-1¡ã; semicarbazone, m. 222-4¡ã. ¦Â-Benzoyl-¦Á-methylpropionic acid (50 g. from 60 g. pyrotartaric anhydride and AlCl₃ in C₆H₆, m. 139-40¡ã. PhCH₂– CH₂CHMeCO₂H, b₁₅ 174¡ã; anilide, m. 140¡ã. 2-Me derivative of I (2 g. from 5 g. of the above acid), b₁₅ 132¡ã, slowly turns brown in the air; semicarbazone, formed exceedingly slowly (3 days), m. 199-201¡ã. Below are given, resp., t¡ã, d₄^t and n for ¦Á, D, ¦Â and ¦Ã at t¡ã for the derivatives of I: ac-2-Me, 20.9¡ã, 1.0600, 1.54669, 1.55154, 1.56542, 1.57764; 7-Me, 35.0¡ã, 1.0569, 1.55168, 1.55674, 1.57160, 1.58479; 7-Et, 17.2¡ã, 1.0556, 1.55478, 1.55988, 1.57454, 1.58752; 5,7-Me₂, 15.5¡ã, 1.0654, 1.55986, 1.56496, 1.57971, 1.59284. Derivatives of tetrahydronaphthalene: ar-2-Me, 15.1¡ã, 0.9541, 1.53316, 1.53719, 1.54907, 1.55897; ar-2-Et, 17.6¡ã, 0.9499, 1.53072, 1.53474, 1.54627, 1,55594; ar-1,3-Me₂, 21.0¡ã, 0.9589, 1.53683, 1.54094, 1.55287.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Canonica, L. published the artcileThe hypocholesterolemic action of some synthetic compounds, SDS of cas: 1949-41-3, the publication is Drugs Affecting Lipid Metab., Proc. Symp., Milan (1961), 328-35, database is CAplus.

The anti-cholesterolemic effect of some phenylsubstituted aliphatic carboxylic acids was examined by their effect on the hyper-cholesterolemia induced in rats by intraperitoneal injection of 500 mg./kg. of Triton WR 1339, blood cholesterol being determined 22 hrs. after injection by Bloor’s method and the effect evaluated statistically. Toxicity of the compounds in mice and the min. dose giving a significant reduction in blood cholesterol were determined Thirty-four compounds were synthesized and tested; these were in 6 groups in which a phenyl group was introduced in various positions along an aliphatic C chain. The groups were: butyric acids; valeric and isovaleric acids; methylbutyric acids; unsaturated acids with isoprenoid structures; diand tetrahydrogeranic acids; and mevalonic acids. Among ¦Á-phenylbutyric acids, para substitution of OH and NH₂ resulted in inactive compounds whereas the p-Cl, -Me, and -OMe compounds were active. Phenyltetrahydrogeranic acid and phenylmevalonic acid derivatives were inactive. Phenyl derivatives of C₅ acids with a branched chain were active, particularly ¦Â-benzylidenebutyric (I), ¦Á-methyl-¦Ã-phenylbutyric (II), ¦Á-benzylbutyric (III), ¦Á-phenyldimethylacrylic (IV), and ¦Â-phenylisovaleric (V) acids. The L.D.₅₀ (mice mg./kg.), min. effective dose (mg./kg.), and therapeutic index of these were: I, 520, 130, 4; II, 712, 71, 10; III, 1068, 215, 4; IV, 1700, 340, 5; V, 1550, 387, 4. The only active straight-chain compound was ¦Â-phenylvaleric acid (748, 249, 3).. Biosynthesis of fatty acids from acetate-1-C¹⁴ was inhibited by I, IV, and V to varying degrees; cholesterol synthesis was similarly inhibited by I and cholesterol synthesis from mevalonate-2-C¹⁴ was inhibited by all except II. The anticholestcrolemic effect of I was confirmed clin. with doses of 200 mg./day.

Drugs Affecting Lipid Metab., Proc. Symp., Milan published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, SDS of cas: 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zhu, Ru-Yi published the artcileLigand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp³)-H Bonds, Quality Control of 1949-41-3, the publication is Journal of the American Chemical Society (2017), 139(16), 5724-5727, database is CAplus and MEDLINE.

We herein report the palladium(II)-catalyzed bromination and iodination of a variety of ¦Á-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp³)-H bromination, enabled by quinoline ligands.

Journal of the American Chemical Society published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C15H21BO2, Quality Control of 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kay, H. D. published the artcileMode of oxidation of fatty acids with branched chains. III. The fats in the body of ¦Á-methylcinnamic acid, ¦Â-phenylisobutyric acid and ¦Ã-phenylisovaleric acid, SDS of cas: 1949-41-3, the publication is Biochemical Journal (1924), 153-60, database is CAplus and MEDLINE.

The end product of C₆H₅CH:C(CH₃)COOH and of C₆H₅CH₂CH(CH₃)COOH is benzoic acid, that of C₆H₅CH₂CH₂CH(CH₃)COOH is phenylacetic acid. Acids with branched chains-as above-are oxidized as the parent acids with normal chains.

Biochemical Journal published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, SDS of cas: 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Hong, Seung Youn published the artcileSelective formation of ¦Ã-lactams via C-H amidation enabled by tailored iridium catalysts, Name: 2-Methyl-4-phenylbutanoic acid, the publication is Science (Washington, DC, United States) (2018), 359(6379), 1016-1021, database is CAplus and MEDLINE.

Intramol. insertion of metal nitrenes into C-H bonds to form ¦Ã-lactam rings has traditionally been hindered by competing isocyanate formation. The application of theory and mechanism studies to optimize a class of Ir(III) pentamethylcyclopentadienyl catalysts for suppression of this competing pathway is reported. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by d. functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding ¦Ã-lactams via sp³ and sp² C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the late-stage functionalization of amino acid derivatives and other bioactive mols.

Science (Washington, DC, United States) published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Name: 2-Methyl-4-phenylbutanoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Premasagar, Vuppalapaty published the artcileMethanesulfonic acid catalyzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones, Computed Properties of 1949-41-3, the publication is Journal of Organic Chemistry (1981), 46(14), 2974-6, database is CAplus.

The title cyclizations were carried out by heating anhydrous MeSO₃H with the 3-arylpropanoic or 4-arylbutanoic acid at 110-15 and 90-5¡ã, resp. Using MeSO₃H as a Friedel-Crafts catalyst is not promising (2,4-Me₂C₆H₃COMe yield from m-xylene was ?30%).

Journal of Organic Chemistry published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Computed Properties of 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Yabuuchi, Tetsuya published the artcileApplication of phenylglycine methyl ester (PGME) to determination of the absolute configuration of carboxylic acids having phenylalkyl group, COA of Formula: C11H14O2, the publication is Chirality (1997), 9(5/6), 550-555, database is CAplus.

(S)-phenylglycine Me ester [(S)-PGME] was applied to elucidate the absolute configuration of a series of aliphatic carboxylic acids Ph(CH₂)_nCHRCO₂H (I; n = 1-6; R = Me, Et) which possess a Ph group on the chain, by the process similar to the modified Mosher’s method. (S)-PGME was condensed with rac-I, and the resulting diastereomeric pair was separated ¦¤¦Ä Values were calculated from the ¹H-NMR chem. shifts of the diastereomeric PGME amides. By analyzing the pos. and neg. distribution patterns for each compound, it was concluded that this new method was successful to predict the absolute configuration of such type of acids, and that no significant interaction between the two Ph groups, one in the chain and the other in the PGME, was present.

Chirality published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C15H10O2, COA of Formula: C11H14O2.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Huang, Liangbin published the artcileReductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes, HPLC of Formula: 1949-41-3, the publication is Angewandte Chemie, International Edition (2017), 56(39), 11901-11905, database is CAplus and MEDLINE.

A new method for the synthesis of terminal and internal alkynes from the Ni-catalyzed decarboxylative coupling of N-hydroxyphthalimide esters and bromoalkynes is presented. This reductive cross-electrophile coupling is the 1st to use a C(sp)-X electrophile, and appears to proceed via an alkynylnickel intermediate. The internal alkyne products were obtained in yields of 41-95% without the need for a photocatalyst, light, or a strong oxidant. The reaction displays a broad scope of carboxylic acid and alkyne coupling partners, and can tolerate an array of functional groups, including carbamate NH, halogen, nitrile, olefin, ketone, and ester moieties. Mechanistic studies suggest that this process does not involve an alkynylmanganese reagent and instead proceeds through Ni-mediated bond formation.

Angewandte Chemie, International Edition published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, HPLC of Formula: 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Fischer, Ernst Otto published the artcileAromatic complexes of metals. XXII. Thiophenechromiumtricarbonyl, Recommanded Product: 2-Methyl-4-phenylbutanoic acid, the publication is Chemische Berichte (1958), 2395-9, database is CAplus.

Cr-(CO)₆ (I) and thiophene (II) heated in a sealed tube gave II. Cr(CO)₃ (III) and 3 equivalents CO. The diamagnetic III, which is in the crystalline state fairly stable in air, demonstrates for the 1st time also that aromatic heterocycles are capable of binding transition metals centrally through their ¦Ð-electron sextet. I (2.2 g.) and 40 cc. pure II heated 5-7 hrs. in a sealed tube under N at 205-10¡ã, cooled, filtered under N, and evaporated in vacuo, the deep orange-red, crystalline residue dissolved in a few cc. 1:1 C₆H₆-petr. ether, and chromatographed on Al₂O₃, a yellow zone washed out, the orange-red zone eluted with C₆H₆, the deep orange-red eluate evaporated, and the residue sublimed in vacuo at 85-95¡ã yielded 60-75 mg. III, red crystals. The molar magnetic susceptibilities of III at 293 and 90¡ãK. were -168 and -163 ¡Á 10^-6 cu. cm./mole, resp.

Chemische Berichte published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Recommanded Product: 2-Methyl-4-phenylbutanoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Le, Ky Khac Anh published the artcile1-Aminopyridinium Ylides as Monodentate Directing Groups for sp³ C-H Bond Functionalization, Recommanded Product: 2-Methyl-4-phenylbutanoic acid, the publication is Journal of the American Chemical Society (2019), 141(37), 14728-14735, database is CAplus and MEDLINE.

1-Aminopyridinium ylides are efficient directing groups for palladium-catalyzed ¦Â-arylation and alkylation of sp³ C-H bonds in carboxylic acid derivatives The efficiency of these directing groups depends on the substitution at the pyridine moiety. The unsubstituted pyridine-derived ylides allow functionalization of primary C-H bonds, while methylene groups are unreactive in the absence of external ligands. 4-Pyrrolidinopyridine-containing ylides are capable of C-H functionalization in acyclic methylene groups in the absence of external ligands, thus rivaling the efficiency of the aminoquinoline directing group. Preliminary mechanistic studies have been performed. A cyclopalladated intermediate has been isolated and characterized by X-ray crystallog., and its reactivity was studied.

Journal of the American Chemical Society published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Recommanded Product: 2-Methyl-4-phenylbutanoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia