3290-53-7

Usage

Uses

It is used as an active pharmaceutical intermediate.

InChI:InChI=1/C10H12/c1-9(2)8-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3

Upstream product

• 515-40-2 neophyl chloride 
• 60-35-5 acetamide 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 62726-47-0 β-phenylisovaleryl peroxide 
• 21816-03-5 2-phenyl-2-methylpropyl tosylate 
• 18292-38-1 2-methallyltrimethylsilane 
• 71-43-2 benzene 
• 917-64-6 methyl magnesium iodide 
• 58547-43-6 2-benzyl-2-methylsulfanyl-[1,3]dithiane 
• 187737-37-7 propene 
• 591-51-5 phenyllithium 
• 563-47-3 3-Chloro-2-methylpropene 

Downstream Products

• 69278-45-1 2-Methoxy-2-methyl-1-phenyl-propane 
• 117506-41-9 1-phenyl-2-methyl-2-methoxy-3-bromopropane 
• 42759-98-8 2-methyl-3-phenyl-2-propenyl thiocyanate 
• 106119-20-4 2-benzyl-2-propenyl thiocyanate 
• 106119-29-3 2-benzyl-2-propenyl isothiocyanate 
• 106119-19-1 2-acetoxy-2-methyl-3-phenylpropyl thiocyanate 
• 36099-42-0 (+/-)-2-methyl-3-phenyl-1,2-epoxypropane 
• 90926-14-0 rac-2-methyl-3-phenyl-1,2-propanediol 
• 1235453-99-2 1-phenyl-3-methyl-3-phenylmethylcyclobut-1-ene 
• 1253695-46-3 4-[5-benzyl-5-methyl-2-phenyl-4,5-dihydrofuran-3-ylsulfonyl]benzonitrile 
• 1253695-47-4 4-[5-benzyl-2-(4-cyanophenyl)-5-methyl-4,5-dihydrofuran-3-ylsulfonyl]benzonitrile 
• 1253695-48-5 4-[5-benzyl-3-(4-bromophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl]benzonitrile 
• 1253695-50-9 4-[5-benzyl-2-(4-bromophenyl)-5-methyl-4,5-dihydrofuran-3-ylsulfonyl]benzonitrile 
• 1253695-45-2 4-[5-benzyl-5-methyl-3-(phenylsulfonyl)-4,5-dihydrofuran-2-yl]benzonitrile 

Relevant academic research and scientific papers

Catalytic, contra-Thermodynamic Positional Alkene Isomerization

The positional isomerization of C═C double bonds is a powerful strategy for the interconversion of alkene regioisomers. However, existing methods provide access to thermodynamically more stable isomers from less stable starting materials. Here, we report

Contra-Thermodynamic Positional Isomerization of Olefins

A light-driven method for the contra-thermodynamic positional isomerization of olefins is described. In this work, stepwise PCET activation of a more substituted and more thermodynamically stable olefin substrate is mediated by an excited-state oxidant an

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

Construction of C-C Bond via C-N and C-O Cleavage

The construction of a C-C bond is a center subject in synthetic organic chemistry. The cross-electrophile coupling has provided a powerful tool to forge the C-C bond. However, this process generally requires organic halides, which has severely restricted

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes

A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C?Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes.

Action of Organoaluminum Reagents on Esters: Alkene Production and the Degradation of Synthetic Lubricants

Reactions of methylaluminum reagents with ester-based lubricating oils are mimicked through the reaction of trimethylaluminum (TMA) with tetraesters C(CH2OC(O)R)4 (R = C5H11 4Pent, Bn 4Bn). Using a 2:1 stoichiometry gave adduct 4Pent(TMA)4. NMR spectroscopy on 1:1-12:1 TMA/4Pent systems suggested 4Pent gave dimethylated adduct C5H11CMe2OAlMe2(TMA), 2Pent(TMA). Similar combination of TMA with 4Bn at raised temperatures transformed 4Bn into C(CH2OAlMe2)4(2Bn)4 5(2Bn)4 by sequential reaction of each ester group. Doubly reacted {BnC(O)OCH2}2C(CH2OAlMe2)2(2Bn)2 7Bn(2Bn)2 was isolated and characterized. A Mitsubishi molecule could also be isolated, its formation rationalized by the elimination of 2Bn and TMA from 5(2Bn)4. The action of MenAlCl3-n (n = 1, 1.5, 2) was studied initially on monoester BnC(O)OMe 1Bn. Combining excess Me2AlCl with 1Bn gave adduct 1Bn(Me2AlCl) and small amounts of dimethylated BnCMe2OAlMe2(Me2AlCl), 2Bn(Me2AlCl), and MeOAlCl2 10. 2Bn(Me2AlCl) was fully characterized and, in the presence of 10, acted as a source of 2Bn(MeAlCl2). From this species, a mixture of alkenes could be generated by formal elimination of Me3Al2(OH)Cl2 13, the decomposition of which was presumed to also explain MeH observation. Replacing Me2AlCl with aluminum sesquichloride or MeAlCl2 led to progressively more sluggish but similar reactions. Using MenAlCl3-n (n = 1, 1.5, 2) with tetraesters suggested similar reactivity to monoesters.

Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.

CATALYSTS AND METHODS FOR FORMING ALKENYL AND ALKYL SUBSTITUTED ARENES

Embodiments of the present disclosure provide for Rh(I) catalysts, methods of making alkenyl substituted arenes (e.g., allyl arene, vinyl arene, and the like), methods of making alkyl substituted arenes, and the like.

Reactivity of a Palladacyclic Complex: A Monodentate Carbonate Complex and the Remarkable Selectivity and Mechanism of a Neophyl Rearrangement

The ligand N(CH2-2-C5H4N)2(CH2CH2CH2OH), L1, reacted with [Pd(CH2CMe2C6H4)(COD)] to give a new fluxional cycloneophyl organopalladium complex [Pd(CH2CMe2C6H4)(κ2-L1)], 1, which on attempted recrystallization from THF gave the monodentate carbonate complex [Pd(CO3)(κ3-L1)], 2. Complex 2 was prepared in designed syntheses by reaction of [PdCl(κ3-L1)]+ with silver carbonate or by reaction of [Pd(OH)(κ3-L1)]+ with CO2. Complex 1 reacted with aqueous CO2 to give the cationic neophylpalladium complex [Pd(CH2CMe2C6H5)(κ3-L1)]+(HCO3)-, 6. Complex 6 reacts with hydrogen peroxide to give complex 2 with release of a mixture of organic products, the major one being 2-phenyl-2-butanol, PB. The formation of PB involves a neophyl rearrangement with the unprecedented preference for methyl over phenyl migration. A mechanistic basis for this unexpected reaction is proposed, involving β-carbon elimination at a palladium(IV) center.