Category: 1949-41-3

Fujita, T. published the artcileThe reaction of carboxylic acids with conjugated olefins using sodium naphthalenide in the presence of N,N,N’,N’-tetramethylethylenediamine, Application In Synthesis of 1949-41-3, the publication is Synthesis (1979), 310-11, database is CAplus.

4-Phenylbutanoic acids Ph(CH₂)₂CRR¹CO₂H (R = H, Me; R¹ = H, C₁-C₄ alkyl) were prepared in 5-46% yields by treating PhCH:CH₂ with RR¹CHCO₂H in THF in the presence Na or Li naphthalenide and (Me₂NCH₂)₂. Similar reaction of Me₂CHCO₂H with isoprene or myrcene gave R²CH₂CMe:CHCH₂CMe₂CO₂H (R² = H, Me₂C:CHCH₂) in 66 and 33% yields, resp.

Synthesis 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, Application In Synthesis of 1949-41-3.

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

Liu, Xuesong published the artcileSilver-Catalyzed Decarboxylative Alkynylation of Aliphatic Carboxylic Acids in Aqueous Solution, Name: 2-Methyl-4-phenylbutanoic acid, the publication is Journal of the American Chemical Society (2012), 134(35), 14330-14333, database is CAplus and MEDLINE.

C(sp³)-C(sp) bond formations are of immense interest in chem. and material sciences. We report herein a convenient, radical-mediated and catalytic method for C(sp³)-C(sp) cross-coupling. Thus, with AgNO₃ as the catalyst and K₂S₂O₈ as the oxidant, various aliphatic carboxylic acids underwent decarboxylative alkynylation with com. available ethynylbenziodoxolones in aqueous solution under mild conditions. This site-specific alkynylation is not only general and efficient but also functional group compatible. In addition, it exhibits remarkable chemo- and stereoselectivity.

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, Name: 2-Methyl-4-phenylbutanoic acid.

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

Liu, Chao published the artcileSilver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution, Computed Properties of 1949-41-3, the publication is Journal of the American Chemical Society (2015), 137(31), 9820-9823, database is CAplus and MEDLINE.

We report herein an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids. Thus, with AgNO₃ as the catalyst and K₂S₂O₈ as the oxidant, the reactions of various aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous CH₃CN solution afforded the corresponding alkyl azides under mild conditions. A broad substrate scope and wide functional group compatibility were observed A radical mechanism is proposed for this site-specific azidation.

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, Computed Properties of 1949-41-3.

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

Li, Bo published the artcileSynthesis of Oxazolines from Amides via Palladium-Catalyzed Functionalization of Unactivated C(sp³)-H Bond, Formula: C11H14O2, the publication is Organic Letters (2015), 17(5), 1200-1203, database is CAplus and MEDLINE.

A complementary method that enables the expeditious synthesis of oxazolines from amides via Pd-catalyzed C(sp³)-H functionalization has been described. Preliminary studies indicate that the reaction might go through a chlorination/nucleophilic cyclization sequence, and the high efficiency of this sequence is enhanced by the in situ cyclative capture of the chlorinated intermediate. The resulting oxazolines can be further converted into the corresponding ¦Â-amino alcs. without chromatog.

Organic Letters 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, Formula: C11H14O2.

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

Ren, Wenlong published the artcilePd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid, Application In Synthesis of 1949-41-3, the publication is Organic Letters (2022), 24(3), 886-891, database is CAplus and MEDLINE.

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH was described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Organic Letters 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, Application In Synthesis of 1949-41-3.

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

Fieser, Louis F. published the artcileVitamin K activity and structure, SDS of cas: 1949-41-3, the publication is Journal of Biological Chemistry (1941), 659-92, database is CAplus.

The vitamin K activity of various quinones (uniform testing technique was used) was re?xamd., these results superseding all previous data (C. A. 34, 1649.8, 3724.3, 7895.4-5, 6336.7). 2-Methyl-1,4-naphthoquinone (I) was 3.3 times as effective as synthetic K₁. The following group of 2,3-disubstituted 1,4-naphthoquinones had the min. EDs indicated: 2-methyl-3-phytyl, 2-methyl-3-farnesyl, 2-methyl-3-(¦Â,¦Ã-dihydrophytyl), 2-methyl-3-geranyl, 2-methyl-3-cinnamyl, 2-methyl-3-(¦Â,¦Ã,¦Ã,-trimethylallyl), 2,3-di-Me, 2-methyl-3-benzyl, 2-methyl-3-hydrocinnamyl: 1, 5, 8, 25, 25, 50, 50, 200 and 300 ¦Ã, resp. The dihydro K₁ with an activity of 8 was much more active than previous reports indicated (C. A. 34, 5437.7, 5493.4). Comparison of ¦Â-alkenyl derivatives shows that activity increases with length of chain to 20 C atoms, after which it is little affected by further increase in length. Of the monosubstituted 1,4-naphthoquinones, I, phytyl, farnesyl, ¦Â,¦Ã-dihydrophytyl, allyl, geranyl, Et and Pr were effective in doses of 0.3, 50, 500, 600, 800 and 1000 ¦Ã, resp., the last two being inactive. EDs for other 1,4-naphthoquinones were as follows: 2-ethyl-3-phytyl, 2,3-diallyl, and 2,7-di-Me, 1000 ¦Ã; 2,5-di-Me and 2,8-di-Me, 500 ¦Ã (slight); 2,6-dimethyl-3-phytyl, 2,6-di-Me, 6,7-di-Me, inactive at 1000. 1,1-Dimethyl-3-tert-butyl- and 2-(¦Ä-methyl-¦Ã-pentenyl)-1,4-dihydroanthraquinones were inactive at 1000 ¦Ã. Of the naphthoquinones containing O substituents, plumbagin and phthiocol had EDs at 400 and 500 ¦Ã, resp., while juglone, lawsone, lapachol, 2-¦Â-heptenyl-3-hydroxy-, 2-farnesyl-3-hydroxy-, and 2-methyl-3-(¦Ã-hydroxydihydrophytyl)-1,4-naphthoquinone, were inactive at 1000 ¦Ã, as was also hydroquinone diacetate; 2-methyl-3-carbethoxy-1,4-naphthohydroquinone, however, showed an ED of 25 ¦Ã, presumably because of conversion into 2-methylnaphthoquinone. Many of the oxides prepared from the quinones are active: vitamin K₁, I, 2,3-dimethyl-, 2-methyl-3-cinnamyl-, 2-phytyl-, 2-farnesyl- and 2,7-dimethyl-1,4-naphthoquinone oxides had EDs of 1.2, 5, 25, 150, 200, 1000 ¦Ã and inactive, resp. Vitamin K oxide is much less affected by light than the quinone form. Exposure to sunlight for 2 h. decreased the activity of the latter 90%, and of the former 30%. The vitamin may exist as the oxide in green plants. 2-Methyl-2-phytyl-2,3-dihydro-1,4-naphthoquinone and naphthotocopherol required 50 and 500 ¦Ã, resp., for an ED. The latter is of particular interest because it shows both vitamin E and vitamin K activity. Of the ethers and esters of 1,4-naphthohydroquinones (II), the Na salts of the 2-methyl-II diphosphoric acid ester, 2-methyl-II disulfuric acid ester, and 2,3-dimethyl-II disulfuric acid ester required for ED 0.5, 2 and 500 ¦Ã given orally (0.5 and 1-2 i.v.); vitamin K hydroquinone diphosphoric acid, 50 ¦Ã given orally, 10 i.v.; disulfuric acid ester, K salt, inactive at 500 ¦Ã. The following organic esters and ethers of 2-methyl-1,4-naphthohydroquinone had the ED indicated: di-Ac, di-Bz, dimesitoate, mono-Et ether, di-Me ether, dibenzyl ether, 1, 1, 300, 1, 5 and 7 ¦Ã, resp. 5,8-Dihydro- and ¦Â,¦Ã,5,6,7,8-hexahydrovitamin K₁, 5,8-dihydro-I, 5,8,9,10-tetrahydro-I and 5,6,7,8-tetrahydro-I had EDs of 4, 1000, 6, 8 and 500 ¦Ã, resp. The following naphthols and tetralones likewise showed high activity where biol. conversion to I could occur: I, 2-methyl-, 3-methyl-, and 4-methyl-1-naphthol, 1-methyl-, 3-methyl-2-naphthol, 1-naphthol, 2-methyl-, and 3-methyl-1-tetralone, 2-methyl-1-naphthylamine, 2-methylnaphthalene (II) and ¦Á-methyl-¦Ã-phenylbutyric acid (III) had the following EDs: 0.5, 1, 0.6, next 3 inactive at 1000, 1000, 0.6, 1, 5, 1000 and inactive at 1000 ¦Ã, resp. The organism does not appear able to oxidize II effectively or to cyclize III. The 2- and 3-methyltetralones are the stages furthest removed from the vitamin which are effectively converted to it by the organism.

Journal of Biological 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, SDS of cas: 1949-41-3.

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

Horii, Zenichi published the artcileItaconic acid in organic chemistry. I. Synthesis of 2-methyl-1,4-naphthoquinone (menadione), Category: catalysis-chemistry, the publication is Pharmaceutical Bulletin (1957), 82-4, database is CAplus and MEDLINE.

The easy availability of itaconic acid (I) led to its use in the synthesis of the title compound (II). The anhydride of I was converted by the Friedel-Crafts reaction with C₆H₆ and AlCl₃ to BzCH:CMeCO₂H (Dixon, et al., C.A. 44, 1516a), which (4 g.) refluxed 24 hrs. with amalgamated Zn (from 16 g. mossy Zn and 1.6 g. HgCl₂) in 14 cc. concentrated HCl, 6 cc. H₂O, 8 cc. PhMe, and 0.4 cc. AcOH, plus 4 cc. addnl. concentrated HCl each 6 hrs., cooled, the aqueous layer extracted with ether, and the extract distilled underwent the Clemmensen reduction to 1.7 g. Ph(CH₂)₂CHMeCO₂H (III), b₃ 138-40¡ã. III was also prepared by the catalytic hydrogenation of I to methylsuccinic acid according to D., et al. (loc. cit.), whose anhydride was converted to BzCH₂CHMeCO₂H, thence to III, and finally to 3,4-dihydro-2-methyl-1(2H)-naphthalenone (IV), all according to Alexander and Mudrak (C.A. 44, 10693i). IV (6 g.) in 60 cc. AcOH oxidized by 12 g. CrO₃ in 60 cc. 80% AcOH at such a rate as to keep the temperature below 20¡ã, the mixture kept 36 hrs. at room temperature, and poured into ice H₂O yielded 1.8 g. II, m. 104¡ã. Or, IV (14.7 g.) in 200 cc. ether treated gradually below 5¡ã with 16 g. Br, stirred 1.5 hrs., and worked up as usual yielded 17.5 g. 2-Br derivative of IV, m. 66¡ã, and this (1 g.) refluxed 30 min. with 2.5 g. 2,4,6-collidine yielded 0.5 g. 2-methyl-1-naphthol (V), m. 61¡ã. V (1 g.) in 10 cc. AcOH oxidized below 20¡ã by the gradual addition of 1.2 g. CrO₃ in 80% AcOH, kept 48 hrs., and poured into ice H₂O yielded 0.4 g. II. The structure of II was confirmed by reductive acetylation (Fieser, et al., C.A. 34, 413²) with AcONa, Zn dust, AcOH, and Ac₂O to 1,4,2-(AcO)₂C₁₀H₅Me, m. 112¡ã.

Pharmaceutical Bulletin 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, Category: catalysis-chemistry.

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

Besancon, Jack published the artcileMetallocenes. XVII. Attempts to classify the diastereogenic reactions of benchrotrenes. Study of their stereoselectivity, Recommanded Product: 2-Methyl-4-phenylbutanoic acid, the publication is Bulletin de la Societe Chimique de France (1971), 1804-14, database is CAplus.

The reduction of benchrotrenes (I) to the corresponding asym. alc. is stereoselective, and the reactions of II with Cr(CO)6 is not stereoselective. Thus, (-)-(1S)-2-hydroxy-1-propionylbenchrotrene [(-)-III] is treated with KBH4 to give (+)-(1S)-2-hydroxy-1-[(1S)-hydroxypropyl]benchrotrene (IV) (major product) and (+)-(1S)-2-hydroxy-1-[(1R)-hydroxypropyl]benchrotrene (V). A mixture of (-)-(1S)-2-methoxy-1-[(1R)-hydroxypropyl]benchrotrene (VI) (major product) and (-)-(1S)-2-methoxy-1-[(1S)-hydroxypropyl]benchrotrene (VII) is obtained from (+)-(1S)-2-methoxy-1-propionylbenchrotrene [(+)-VII]. II (R = Me, R1 = H) is treated with Cr(CO)6 to give an equimolar mixture of IX and X.

Bulletin de la Societe Chimique de France 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

Yang, Xinglin published the artcileAuxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp³)-H bonds at room temperature, Application In Synthesis of 1949-41-3, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(38), 6423-6426, database is CAplus and MEDLINE.

The direct transformation of unactivated C(sp³)-H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance. Some drugs and natural products were readily modified by this method. Merged with substitution reaction, newly formed C-X bonds can be transformed into diverse C-O, C-S, C-C and C-N bonds. A preliminary mechanism study demonstrates that solvent is crucial for C-H activation and the C-H activation step is involved in the rate-limiting step. An isolated Pd(II) intermediate can be transformed into a halogenated product with the retention of conformation which suggests that concerted reductive elimination from Pd(II) to form a C-X bond was favored.

Chemical Communications (Cambridge, United Kingdom) 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 C23H20BN, Application In Synthesis of 1949-41-3.

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

Candish, Lisa published the artcileCatalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation, Formula: C11H14O2, the publication is Chemistry – A European Journal (2016), 22(29), 9971-9974, database is CAplus and MEDLINE.

The catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids such as 4-(4-bromophenoxy)butanoic acid, 1-tosylpiperidine-4-carboxylic acid, adamantan-1-carboxylic acid are reported. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.

Chemistry – A European 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, Formula: C11H14O2.

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