4374-44-1

Usage

InChI:InChI=1/C12H16O2/c1-12(2,11(13)14)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3,(H,13,14)

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 79-31-2 isobutyric Acid 
• 621-82-9 Cinnamic acid 
• 538-42-1 sodium cinnamate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 15732-89-5 (E)-2,2-dimethyl-4-phenylbut-3-enoic acid 
• 140-10-3 cis-cinnamic acid 
• 94041-88-0 methyl (E)-2,2-dimethyl-4-phenyl-3-buten-1-oate 
• 38795-58-3 2-methyl-4-phenylbutyric acid methyl ester 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 14308-33-9 2,2-dimethoxy-3,3-dimethyl-5-phenyl-2,3-dihydro-furan 
• 71-43-2 benzene 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 

Downstream Products

• 15732-85-1 2,2-dimethyl-4-phenyl-butan-1-ol 
• 1361152-14-8 tert-butyl 2,2-dimethyl-4-phenylbutaneperoxoate 
• 103-07-1 1,1-dimethyl-3-phenylpropyl acetate 
• 79399-13-6 N-[1,1-dimethyl-3-phenylpropyl]acetamide 
• 20215-55-8 dihydro-3,3-dimethyl-5-phenylfuran-2(3H)-one 
• 1439367-46-0 (2,2-dimethyl-4-phenyl-butyl) 2-oxopyridine-1-carboxylate 
• 1439367-45-9 (2,2-dimethyl-4-phenyl-butyl) 2-pyridyl carbonate 
• 40654-84-0 2,2-dimethyl-4-phenylbutanal 

Relevant academic research and scientific papers

Intramolecular Oxidative Coupling between Unactivated Aliphatic C-H and Aryl C-H Bonds

Direct oxidative coupling of different inert C-H bonds is the most straightforward and environmentally benign method to construct C-C bonds. In this paper, we developed a Pd-catalyzed intramolecular oxidative coupling between unactivated aliphatic and aryl C-H bonds. This chemistry showed great potential to build up fused cyclic scaffolds from linear substrates through oxidative couplings. Privileged chromane and tetralin scaffolds were constructed from readily available linear starting materials in the absence of any organohalides and organometallic partners.

Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

The development of practical C-H/C-H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C-C bonds. Herein we report a cyclative C(sp3)-H/C(sp2)-H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant and generates water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, can be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through sequential functionalizations of four C-H bonds.

Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents

This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.

Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling

A facile and general method for copper-catalyzed decarboxylative alkylcarboxylation of cinnamic acids with dimethyl 2,2′-azobis(2-methylpropionate) has been developed. The scope and versatility of the reaction was demonstrated, and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to provide desired β,γ-unsaturated esters in moderate to good yields. Moreover, α,β-unsaturated acids with a carbonyl group on the γ-position of acrylic acids also smoothly proceeded to furnish the desired products in good yields.

Synthesis, biological evaluation, and 3D QSAR study of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters as N -acylethanolamine acid amidase (NAAA) inhibitors

N-(2-Oxo-3-oxetanyl)carbamic acid esters have recently been reported to be noncompetitive inhibitors of the N-acylethanolamine acid amidase (NAAA) potentially useful for the treatment of pain and inflammation. In the present study, we further explored the

DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Fluorine transfer to alkyl radicals

The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F - or F+). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F?). A new approach to alkyl fluorination has been developed that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alkyl radicals. This approach is successful for a broad range of alkyl radicals, including primary, secondary, tertiary, benzylic, and heteroatom-stabilized radicals. Furthermore, calculations reveal that fluorine-containing ionic reagents are likely candidates for further expansion of this approach to polar reaction media. The use of these reagents in alkyl radical fluorination has the potential to enable powerful new transformations that otherwise would take multiple synthetic steps.

Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)4 and NaHMDS. Mechanistic investigations support the catalytic nature of Ni0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.

Structure-based optimization of phenylbutyrate-derived histone deacetylase inhibitors

Previously, we developed a strategy to develop a novel class of histone deacetylase (HDAC) inhibitors by tethering short-chain fatty acids with Zn 2+-chelating motifs, which led to N-hydroxy-4-(4-phenylbutyryl-amino) benzamide (HTPB), a hydroxa