5669-14-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2,2-DIMETHYL-3-PHENYLPROPANOIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals for its potential biological and pharmacological properties. It contributes to the development of medicines that address a range of health conditions.
Used in Organic Compounds Production:
In the chemical industry, 2,2-DIMETHYL-3-PHENYLPROPANOIC ACID serves as a building block for the production of other organic compounds. Its unique structure allows for the creation of new compounds that can be utilized in a variety of applications, further expanding its use in medicine and other industries.

InChI:InChI=1/C11H14O2/c1-11(2,10(12)13)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3,(H,12,13)

Upstream product

• 101518-61-0 2,2-dimethyl-3-phenylpropanamide 
• 94800-92-7 ethyl 2,2-dimethyl-3-phenylpropionate 
• 35863-45-7 2,2-dimethyl-3-phenylpropanenitrile 
• 100-44-7 benzyl chloride 
• 79-31-2 isobutyric Acid 
• 1955-45-9 pivalolactone 
• 14248-22-7 methyl 2,2-dimethyl-3-phenylpropionate 
• 100-39-0 benzyl bromide 
• 97-62-1 Ethyl isobutyrate 
• 480453-25-6 ((1-(benzyloxy)-2-methylprop-1-en-1-yl)oxy)trimethylsilane 
• 124-38-9 carbon dioxide 
• 1754-74-1 2-chloro-2-methyl-1-phenylpropane 
• 7647-01-0 hydrogenchloride 
• 1083-30-3 dihydrochalcone 

Downstream Products

• 857771-08-5 2,2-dimethyl-3-(4-nitrophenyl)propanoic acid 
• 62931-24-2 2,2-dimethyl-3-phenylpropanoyl chloride 
• 14248-22-7 methyl 2,2-dimethyl-3-phenylpropionate 
• 10489-28-8 2,2-dimethyl-indan-1-one 
• 72040-69-8 4-nitrophenyl α,α-dimethyl-β-phenylpropionate 
• 100-86-7 2-Methyl-1-phenyl-2-propanol 
• 1754-74-1 2-chloro-2-methyl-1-phenylpropane 
• 41417-90-7 3-cyclohexyl-2,2-dimethylpropanoic acid 
• 443682-78-8 2,2-dimethyl-3-phenylpropionohydroxamic acid 
• 50818-24-1 2,2-dimethyl-3-(4-nitro-phenyl)-propionyl chloride 
• 854210-73-4 2-methyl-1-(4-nitro-phenyl)-2-phenyl-propane 
• 27336-91-0 Diazo-1-dimethyl-3,3-phenyl-4-butanon-2 
• 1195178-08-5 2,2-dimethyl-3-phenylpropanoyl azide 
• 1197-21-3 phentermine hydrochloride 

Relevant academic research and scientific papers

Diradicals Photogeneration from Chloroaryl-Substituted Carboxylic Acids

With the aim of generating new, thermally inaccessible diradicals, potentially able to induce a double-strand DNA cleavage, the photochemistry of a set of chloroaryl-substituted carboxylic acids in polar media was investigated. The photoheterolytic cleavage of the Ar?Cl bond occurred in each case to form the corresponding triplet phenyl cations. Under basic conditions, the photorelease of the chloride anion was accompanied by an intramolecular electron-transfer from the carboxylate group to the aromatic radical cationic site to give a diradical species. This latter intermediate could then undergo CO2 loss in a structure-dependent fashion, according to the stability of the resulting diradical, or abstract a hydrogen atom from the medium. In aqueous environment at physiological pH (pH=7.3), both a phenyl cation and a diradical chemistry was observed. The mechanistic scenario and the role of the various intermediates (aryl cations and diradicals) involved in the process was supported by computational analysis.

Rational design of cannabinoid type-1 receptor allosteric modulators: Org27569 and PSNCBAM-1 hybrids

Allosteric modulation offers an alternate approach to target the cannabinoid type-1 receptor (CB1) for therapeutic benefits. Examination of the two widely studied prototypic CB1 negative allosteric modulators (NAMs) Org27569 and PSNCBAM-1 revealed structural resemblance and similar structure–activity relationships (SARs). In silico docking and dynamics simulation studies using the crystal structure of CB1 co-bound with CP55,940 and Org27569 suggested that Org27569 and PSNCBAM-1 occupied the same binding pocket and several common interactions were present in both series with the CB1 receptor. A new scaffold was therefore designed by merging the key structural features from the two series and the hybrids retained these binding features in the in silico docking studies. In addition, one such hybrid displayed similar functions to Org27569 in dynamic simulations by preserving a key R2143.50-D3386.30 salt bridge and maintaining an antagonist-like Helix3-Helix6 interhelical distance. Based on these results, a series of hybrids were synthesized and assessed in calcium mobilization, [35S]GTPγS binding and cAMP assays. Several compounds displayed comparable potencies to Org27569 and PSNCBAM-1 in these assays. This work offers new insight of the SAR requirement at the allosteric site of the CB1 receptor and provides a new scaffold that can be optimized for the development of future CB1 allosteric modulators.

SUBSTITUTED, SATURATED AND UNSATURATED N-HETEROCYCLIC CARBOXAMIDES AND RELATED COMPOUNDS FOR THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted, saturated and unsaturated N-heterocyclic carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

Mechanism of 8-Aminoquinoline-Directed Ni-Catalyzed C(sp3)-H Functionalization: Paramagnetic Ni(II) Species and the Deleterious Effect of Carbonate as a Base

Studies into the mechanism of 8-aminoquinoline-directed nickel-catalyzed C(sp3)-H arylation with iodoarenes were carried out, to determine the catalyst resting state and optimize catalytic performance. Paramagnetic complexes undergo the key C-H activation step. The ubiquitous base Na2CO3is found to hinder catalysis; replacement of Na2CO3with NaOtBu gave improved catalytic turnovers under milder conditions. Deprotonation of the 8-aminoquinoline derivativeN-(quinolin-8-yl)pivalamide (1a) at the amide nitrogen using NaH, followed by reaction with NiCl2(PPh3)2allowed for the isolation of complex Ni([AQpiv]-κN,N)2(3) with chelating N-donors (where [AQpiv] = C9NH6NCOtBu). Complex3is a four-coordinate disphenoidal high-spin Ni(II) complex, excluding short anagostic Ni-tBu hydrogen interactions. Complex3reacts with the paddle-wheel [Ph3PNi(μ-CO2tBu)2]2(6·PPh3) ortBuCO2H to give insoluble {[AQpiv]Ni(O2CtBu)}2(5). Dissolution of5in donor solvents L (L= DMSO and DMF) gave a paramagnetic intermediate assigned by NMR as [AQpiv]Ni(O2CtBu)L (5·L) and equilibrium reformation of3and6·L. DFT calculations support this equilibrium in solution. Both3and5undergo C-H activation at temperatures as low as 80 °C and in the presence of PR3(PR3= PPh3, PiBu3) to give Ni(C9NH6NCOCMe2CH2-κN,N,C)PR3(7·PR3). The C-H functionalization reaction orders with respect to7·PiBu3, iodoarenes, and phosphines were determined. Hammett analysis using electronically different aryl iodides suggests a concerted oxidative addition mechanism for the C-H functionalization step; DFT calculations were also carried out to support this finding. When Na2CO3is used as the base, the rate determination step for C-H functionalization appears to be 8-aminoquinoline deprotonation and binding to Ni. The carbonate anion was also observed to provide a deleterious NMR-inactive low-energy off-cycle resting state in catalysis. Replacement of Na2CO3with NaOtBu improved catalysis at milder conditions and made carboxylic acid and phosphine additives unnecessary. Complex3and its functionalized analogues were observed as the catalyst resting state under these conditions.

COMPOUNDS FOR SENSING REACTIVE OXYGEN SPECIES AND METHODS FOR USING THE SAME

Provided herein according to some embodiments of the invention are aryl boronate and/or aryl diaminoboryl compounds. Also provided are methods of detecting the presence of hydrogen peroxide (H2O2) and/or other reactive oxygen species (ROS) in a cell and/or tissue by contacting the cell and/or tissue with aryl boronate and/or aryl diaminoboryl compounds. Also provided according to embodiments of the invention are methods of producing persulfides in the presence of hydrogen peroxide (H2O2) and/or other reactive oxygen species (ROS) in a cell and/or tissue by contacting the cell and/or tissue with aryl boronate and/or aryl diaminoboryl compounds.

An Innovative Hydrogen Peroxide-Sensing Scaffold and Insight Towards its Potential as an ROS-Activated Persulfide Donor

Reactive sulfur species, such as hydrogen sulfide, persulfides, and polysulfides, have recently emerged as key signaling molecules and important physiological mediators within mammalian systems. To better assess the therapeutic potential of their exogenou

UREA DERIVATIVES AS CB1 ALLOSTERIC MODULATORS

Heteroaryl and aliphatic analogs of diarylurea-based cannabinoid 1 receptor (CB1 R) allosteric modulators of formula (I) are described. Exemplary analogs can provide improved potencies and pharmacokinetic properties. Methods of using the analogs to treat

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp3)–H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams

The direct Pd-catalyzed β-C(sp3)–H activation and cyclization of aliphatic amides bearing a removable 2-pyridylmethyl directing group with gem-dibromoolefins is described for the first time to construct a variety of γ-lactams. The resulting products with Z- and E-configurations can be easily separated and purified after the reaction, demonstrating the effectiveness and applicability of the method herein developed.

Decarboxylative Giese-Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox-Neutral Protocol

We describe herein a transition-metal-free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4-addition to Michael acceptors. The Fukuzumi catalyst (9-mesitylene-10-methylacridinium perchlorate, [Acr-Mes]ClO4) enabled this transformation under visible-light irradiation at room temperature with CO2 as the only byproduct. The scope and limitations of this protocol were examined by using a range of Michael acceptors (15 examples) and carboxylic acids (18 examples). The use of 3-hydroxypivalic acid in this protocol allowed the straightforward formation of a diastereomerically pure δ-lactone. Moreover, when a homoallylic acid was used, a radical cascade reaction took place with the formation of three C–C bonds.