13305-13-0

Upstream product

• 67-56-1 methanol 
• 18584-20-8 4-methylmandelic acid 
• 622-47-9 4-tolylacetic acid 
• 34966-53-5 methyl 4-methylphenylglyoxylate 
• 104-87-0 4-methyl-benzaldehyde 
• 1353044-15-1 [dimethyl(phenyl)silyl](4-methylphenyl)methanol 
• 1504663-23-3 [dimethylphenylsilyl(p-tolyl)methoxy]trimethylsilane 
• 4815-10-5 2-hydroxy-2-(4-methylphenyl)acetonitrile 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 66985-49-7 2-(4-methylphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 73764-13-3 methyl (4-methylphenyl)diazoacetate 

Downstream Products

• 330551-26-3 2-methyl-1-p-tolyl-propane-1,2-diol 
• 34966-53-5 methyl 4-methylphenylglyoxylate 
• 156276-24-3 methyl 2-[4-(bromomethyl)phenyl]-2-oxoacetate 
• 1584127-63-8 (S)-(+)-methyl 2-acetoxy-2-(4-methylphenyl)acetate 
• 18591-08-7 4-methyl-α-hydroxyphenylacetyl hydrazine 
• 1260146-95-9 C₁₁H₁₅NO₃ 
• 136617-17-9 1-hydroxy-1-(4-methylphenyl)-3-phenylpropan-2-one 
• 32047-03-3 1-(4-methylphenyl)-3-phenylpropan-1,2-dione 
• 1260146-57-3 1-hydroxy-3-phenyl-1-p-tolylpropan-2-one 

Relevant academic research and scientific papers

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

Cobalt-Catalyzed Transfer Hydrogenation of α-Ketoesters and N-Cyclicsulfonylimides Using H2O as Hydrogen Source

A Co-catalyzed effective transfer hydrogenation of various α-ketoesters and N-cyclicsulfonylimides by safe and environmentally benign H2O as hydrogen source is described. The reaction used easily available and easy to handle zinc metal as a reductant. Interestingly, the catalytic system does not require ligand for reduction of N-cyclicsulfonylimides. (Figure presented.).

A containing "1, 3, 4 - oxadiazole thioether" mandelic acid derivatives and use thereof

The invention discloses a containing "1, 3, 4 - oxadiazole thioether" mandelic acid derivatives and their use in the application of the fungi anti-plants sickness, the compound has the general formula (B) structure shown: In the formula, R1 Is H, methyl, fluorine or chlorine, R2 C for containing1 - 3 Straight-chain alkyl, containing C1 - 4 Branched alkyl, propenyl, propynyl or mono-substituted benzyl, wherein the single substituted benzyl substituent is "nitro, methyl, trifluoromethyl, methoxy, three methoxy, fluorine, and bromine". The invention to replace the mandelic acid as the skeleton, mandelic acid introduced in the structure of the "oxadiazole thioether" structure, design synthesizing a containing "1, 3, 4 - oxadiazole thioether" structure of the mandelic acid derivatives, anti-plant disease fungal activity tests show that the class of compounds of plant diseases caused by fungi has good inhibition activity, for the new pesticide research and development and create provide important scientific basis.

Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline

The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.

Ru-MACHO-Catalyzed Highly Chemoselective Hydrogenation of α-Keto Esters to 1,2-Diols or α-Hydroxy Esters

A ruthenium pincer catalyst has been shown to be highly effective for the hydrogenation of a wide range of α-keto esters, affording either diols or hydroxy esters depending on the choice of reaction conditions. Strong base, high temperature, and pressure favor the formation of diols whilst the opposite is true for the hydroxy esters.

P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity

A new, direct and chemoselective esterification of α-hydroxyacids was developed using a reversible covalent-binding strategy. By taking advantage of acetal chemistry, simple aldehydes can be used to efficiently catalyze the esterification of α-hydroxy carboxylic acids in the presence of β-hydroxyacid moieties or other carboxylic acids in amounts equal to or in excess of the alcohols. A diverse array of α-aryl, α-alkyl, α-heteroaryl, and functionalized α-hydroxyacids were smoothly esterified with 1° and 2° alcohols catalyzed by 10 mol% inexpensive and commercially available salicylaldehyde, furnishing the resultant esterification products in 83-95% yields after a simple basic aqueous workup to remove the unreacted hydroxyacids. In addition, the salicylaldehyde can be recovered through vacuum distillation or silica gel purification, thereby meeting the standards of green chemistry. A mechanistic study proved that the formation of covalent adduct III during our proposed catalytic cycle (Scheme 1A) is responsible for the real catalysis.

Enantioselective aerobic oxidation of α-hydroxy-ketones catalyzed by oxidovanadium(V) methoxides bearing chiral, N-salicylidene- tert -butylglycinates

Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N- salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (krel).