40997-78-2

Upstream product

• 5558-66-7 2,2-diphenylpropanoic acid 
• 50354-48-8 methyl 2,2-diphenylpropionate 
• 3469-00-9 methyl 2,2-diphenylacetate 
• 5558-67-8 2,2-diphenylpropionitrile 
• 22875-82-7 2,2-diphenylpropanal 
• 86-29-3 Diphenylacetonitrile 
• 117-34-0 2,2-diphenylacetic acid 

Downstream Products

• 94679-28-4 1-(2,2-diphenyl-propionyl)-4-methyl-piperazine 
• 14295-95-5 2,2-diphenyl-peroxypropionic acid tert-butyl ester 
• 54561-74-9 diphenyl-propionamide 
• 6337-61-7 2,2-diphenyl-propionic acid ethyl ester 
• 19303-32-3 1-methyl-1,3,3-triphenylindane 
• 122020-52-4 N-Butyl-2,2-diphenyl-propionamide 
• 120220-09-9 2,2-Diphenyl-propionic acid 1-methyl-piperidin-4-yl ester 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 403729-94-2 2,2-diphenyl-propionic acid 3-hydroxy-pyridin-2-ylmethyl ester 
• 204850-72-6 3-[[(dimethylamino)carbonyl]oxy]2-(2',2'-diphenylpropionoxymethyl)pyridine 

Relevant academic research and scientific papers

NURR1 RECEPTOR MODULATORS

Described herein, inter alia, are Nurr1 receptor modulators and uses thereof. In an aspect is provided a method for treating a disease associated with dysregulation and/or degeneration of dopaminergic neurons in the central nervous system of a subject in need thereof, the method including administering to the subject in need thereof a therapeutically effective amount of a compound described herein.

Straightforward formation of carbocations from tertiary carboxylic acids: Via CO release at room temperature

We report an unprecedented mode of reactivity of carboxylic acids. A series of tertiary carboxylic acids, containing at least one phenyl α-substituent, undergo loss of carbon monoxide at room temperature (295 K), by a one pot reaction with 0.5-1 molar equivalents of WCl6 in dichloromethane. A plausible mechanism for the Ph3CCO2H/WCl6 reaction, leading to [CPh3][WOCl5] and Ph3CCl, is proposed on the basis of DFT calculations. The analogous reactions involving CEt(Ph)2CO2H, CMe(Ph)2CO2H and CMe2(Ph)CO2H selectively afforded stable hydrocarbons (alkene or indene, depending on the case), apparently resulting from the rearrangement of elusive tertiary carbocations.

Decarbonylation of phenylacetic acids by high valent transition metal halides

Triphenylacetic acid underwent unusual decarbonylation when allowed to react with a series of halides of group 4-6 metals in their highest oxidation state, in dichloromethane at ambient temperature. Thus, the reaction of CPh3COOH with MoCl5, in 1:1 molar ratio, afforded the trityl salt [CPh3][MoOCl4], 1, in 79% yield, while the 1:2 reaction of CPh3COOH with NbF5 afforded [CPh3][NbF6], 2, in 70% yield, NbOF3 being the metal co-product. CPh3COOH reacted with NbCl5, TiF4 and WOCl4 to give mixtures of compounds, however the cation [CPh3]+ was NMR identified in each case. [CPh3][NbCl6], 3, was isolated from NbCl5 and CPh3COCl, prior to being generated from CPh3COOH and PCl5. The reaction of CPh3COOH with TiCl4 was non-selective, and the salt [CPh3][Ti2Cl8(μ-κ2-O2CCPh3)], 4, was obtained in 18% yield. The decarbonylation reactions of CMePh2COCl and CMe2PhCOCl by means of NbCl5 led to the indanes 5a-b, which were isolated in 79-97% yields after hydrolysis of the mixtures and subsequent alumina filtration of the organic phases. The reactions of CH(Ph)2COOH with NbCl5 and WCl6 afforded NbCl4(OOCCHPh2), 6, and CHPh2COCl, respectively, as the prevalent species. CPh2(CH2CH2Br)COOH did not undergo CO release when allowed to interact with WCl6, instead selective intramolecular condensation to C(Ph)2C(O)OCH2CH2, 7, occurred. MeCCCOOH underwent hydrochlorination by WCl6 to give MeC(Cl)CHCOOH, 8, in 72% yield. All the products were fully characterized by elemental analysis, IR and multinuclear NMR spectroscopy. In addition, the solid state structures of 1, 2, 4, 7, and 8 were elucidated by X-ray diffraction.

Transient Kinetics and Quantum Yield Studies of Nanocrystalline α-Phenyl-Substituted Ketones: Sorting Out Reactions from Singlet and Triplet Excited States

Recent work has shown that diarylmethyl radicals generated by pulsed laser excitation in nanocrystalline (NC) suspensions of tetraarylacetones constitute a valuable probe for the detailed mechanistic analysis of the solid-state photodecarbonylation reaction. Using a combination of reaction quantum yields and laser flash photolysis in nanocrystalline suspensions of ketones with different substituents on one of the α-carbons, we are able to suggest with confidence that a significant fraction of the initial α-cleavage reaction takes place from the ketone singlet excited state, that the originally formed diarylmethyl-acyl radical pair loses CO in the crystal with time constants in the sub-nanosecond regime, and that the secondary bis(diarylmethyl) triplet radical pair has a lifetime limited by the rate of intersystem crossing of ca. 70 ns.

Palladium-catalyzed C(carbonyl)-C bond cleavage of amides: a facile access to phenylcarbamate derivatives with alcohols

A sulfur-containing auxiliary enabled palladium-catalyzed C(carbonyl)-C bond activation of amides was reported to form phenylcarbamate derivatives with alcohols. Both alkyl and benzyl alcohols could be employed well with yields up to 85%. Derivations from phenylcarbamates to ureas and thiocarbamates illustrated the potential applications of this sequential C-C cleavage/C-O coupling reaction.

Axially Chiral Dibenzazepinones by a Palladium(0)-Catalyzed Atropo-enantioselective C?H Arylation

Atropo-enantioselective C?H functionalization reactions are largely limited to the dynamic kinetic resolution of biaryl substrates through the introduction of steric bulk proximal to the axis of chirality. Reported herein is a highly atropo-enantioselective palladium(0)-catalyzed methodology that forges the axis of chirality during the C?H functionalization process, enabling the synthesis of axially chiral dibenzazepinones. Computational investigations support experimentally determined racemization barriers, while also indicating C?H functionalization proceeds by an enantio-determining CMD to yield configurationally stable eight-membered palladacycles.

Nickel-Catalyzed oxidative coupling of unactivated C(sp3)-H bonds in aliphatic amides with terminal alkynes

In this work, we demonstrated Ni-catalyzed oxidative coupling of unactivated C(sp3)-H bonds with terminal alkynes for construction of C(sp3)-C(sp) bonds to synthesize alkyl-substituted internal alkynes. Different amides exhibited good compatibility. Preliminary mechanistic studies were conducted to account for this alkynylation.

Nickel-catalysed direct alkylation of thiophenes via double C(sp3)-H/C(sp2)-H bond cleavage: The importance of KH2PO4

A Ni-catalyzed oxidative C-H/C-H cross-dehydrogenative coupling (CDC) reaction was developed for constructing various highly functionalized alkyl (aryl)-substituted thiophenes. This method employs thiophenes and aliphatic (aromatic) amides that contain an 8-aminoquinoline as a removable directing group in the presence of a silver oxidant. The approach enables the facile one-step synthesis of substituted thiophenes with high functional group compatibility via double C-H bond cleavage without affecting C-Br and C-I bonds. DFT calculations verify the importance of KH2PO4 as an additive for promoting C-H bond cleavage and support the involvement of a Ni(iii) species in the reaction.

Copper(II)/Silver(I)-Catalyzed Sequential Alkynylation and Annulation of Aliphatic Amides with Alkynyl Carboxylic Acids: Efficient Synthesis of Pyrrolidones

A highly efficient protocol for the synthesis of pyrrolidones by the copper-catalyzed alkynylation/annulation of aliphatic amides with alkynyl carboxylic acids is discussed in this paper. A broad range of easily accessible alkynyl carboxylic acids were introduced at the β-methyl group of aliphatic amides with the assistance of an 8-aminoquinolyl auxiliary group via decarboxylation to achieve the subsequent cyclic C-N bond formation within one hour. High selectivity of β-methyl groups over methylene groups was observed, and the extension of this catalytic system to the activation of methylene C-H bonds failed. The substrates with two different groups at the α-position of the aliphatic amides lead to the formation of diastereoisomers which is determined by 1H NMR spectroscopy. The initially produced products with Z-configurations can be easily transformed to the corresponding products with E-configurations by the treatment with dilute p-toluenesulfonic acid after the reaction. This catalytic tandem decarboxylative cyclization provides a new opportunity for the direct functionalization of sp3 C-H bonds.

Nickel-catalyzed direct thiolation of C(sp3)-H bonds in aliphatic amides

Nickel-catalyzed thiolation of the inactivated methyl C(sp3)-H bonds of aliphatic amides with disulfide is described. It is a novel strategy for the synthesis of thioethers with the ultimate goal of generating thioether carboxylic acids with various functional groups.