100649-48-7

Upstream product

• 611-70-1 phenyl isopropyl ketone 
• 39158-85-5 2-methyl-1-phenyl-1-trimethylsiloxy-1-propene 
• 20637-27-8 2-deuteriobenzothiazole 
• 59919-11-8 2-methyl-1-phenyl-2-(phenylthio)propan-1-one 
• 100-52-7 benzaldehyde 
• 5170-76-3 2-methyl-1-phenyl-1-acetoxy-1-propene 

Downstream Products

• 100649-50-1 α-(<2-(2)H>isopropyl)-ββ-di-isopropylstyrene 

Relevant academic research and scientific papers

Infrared C-D Stretching and 2H NMR Spectra of Isopropyl-2-d 1-(p-Substituted Phenyl)ethyl Ketons. Evidence for the Hydrogen Bond-Like Interaction between C-D Group and Aromatic ?-Electrons

Isopropyl-2-d 1-(p-X-phenyl)ethyl ketones (where, X=H, NO2, Br, Cl, C2H5, CH3, and NH2) were shown to have two absorption bands in the C-D sterching region.The absorption band at the higher frequency (ca. 2177 cm-1) is assigned to the C-D...? approached conformer, and the high frequency shift is ascribed to the effect of steric compression.Weak C-D...? hydrogen bond was shown to occur by the measurement of the substituent effect on the formation constant and the relative enthalpy of the C-D...? approached conformer

The Effect of Alkyl Groups on Carbanion Stability Part II. Analysis of α- β-Alkyl Substitution on Experimental and Theoretical Acidities

Multivariational analyses were performed to separate the contribution of electronic and steric effects of alkyi groups on the experimental hydrocarbon acidities of four different sets of compounds, consisting of hydrocarbons (SET-I), aeetophenone derivati

A simple method for α-position deuterated carbonyl compounds with pyrrolidine as catalyst

A simple, cost-effective method for deuteration of carbonyl compounds employing pyrrolidine as catalyst and D2O as deuterium source was described. High degree of deuterium incorporation (up to 99%) and extensive functional group tolerance were achieved. It is the first time that secondary amines are used as catalysts for H/D exchange of carbonyl compounds, which also allow the deuteration of complex pharmaceutically interesting substrates. A possible catalytic mechanism, based on the hydrolysis of 1-pyrrolidino-1- cyclohexene, for this pyrrolidine-catalyzed H/D exchange reaction has been proposed. Pyrrolidine has been shown to be an efficient catalyst for deuteration of carbonyl compounds. The method also allowed the deuteration of complex pharmaceutically interesting substrates. Preliminary experiment showed that the enamine and/or iminium activation modes may be involved. Copyright

Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio)isobutyrophenone

In the presence of catalytic amounts of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with α-(phenylthio) isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds.

Triazabicyclodecene: An effective isotope exchange catalyst in CDCl 3

(Chemical Equation Presented) We describe the first effective H/D exchange reaction with acidic substrates in CDCl3 at room temperature. The particularly mild reaction conditions involved (solvent, base, and temperature) allow the chemoselective deuteration of ketones over esters. An NMR study was conducted with the aim of rationalizing the results obtained in the presence of TBD as catalyst.

Investigations into the C-deuteriation of aryl alkyl ketones using urea as a pro-base in the presence of a deuterium donor

Results are reported on the regioselective C-deuteriation of a series of enolates derived from the deprotonation of aryl alkyl ketones using dilithiated urea as the pro-base in the presence of a suitable deuterium donor. Copyright

Catalytic asymmetric synthesis of (S)-oxybutynin and a versatile intermediate for antimuscarinic agents

A practical synthesis of (S)-oxybutynin, a muscarinic receptor antagonist, using catalytic enantioselective cyanosilylation of cyclohexyl phenyl ketone (9a) as a key step is described. The key reaction proceeded with 94% ee using 1 mol% of Gd-1 catalyst,

Investigations into the regioselective C-deuteration of acyclic and exocyclic enolates

Results are reported on the regioselective C-deuteration of a series of related acyclic and exocyclic enolates derived from substituted aryl ketones. We comment on factors, such as the presence of additives and the structural nature of the enolate, that influence the observed C-deuteration and discuss the role of the deuterium donor. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Conformational Analysis of α-Alkyl-ββ-di-isopropylstyrenes. A Dynamic 1H Nuclear Magnetic Resonance Spectroscopic and Molecular Mechanics Investigation

The conformational equilibria and barriers to rotation in α-R-ββ-di-isopropylstyrenes with R=H, Me, Et, Pri, CH2But, and But, and in tri-isopropylethylene and 1,1,2-tri-isopropylpropene investigated by dynamic 1H n.m.r. spectroscopy and molecular mechanics (MM2, MMP2 force fields) are reported.The following conclusions are drawn: (i) the phenyl group is twisted ca. 70-90 degree out of the ethylene plane, (ii) the conformational populations of the geminal isopropyl groups indicate that the effective steric size of the phenyl group is larger than that of methyl, ethyl, isopropyl, and neopentyl groups, but smaller than that of the t-butyl group, (iii) barriers (ΔG(excit.)) to interchange of the isopropyl groups fall in the range 10.5-12.2 kcal mol-1, (iv) molecular mechanics calculations fail to reproduce the experimentally determined conformational populations but satisfactorily reproduce the barriers to rotation of the isopropyl and phenyl groups.According to these calculations the isopropyl group rotations are not correlated.