1081-75-0

Usage

Uses

It is employed as a intermediate for pharmaceutical.

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 3115, 1986 DOI: 10.1021/ja00271a057

InChI:InChI=1/C15H16/c1-3-8-14(9-4-1)12-7-13-15-10-5-2-6-11-15/h1-6,8-11H,7,12-13H2

Upstream product

• 75-09-2 dichloromethane 
• 1121-53-5 benzyl sodium 
• 1083-30-3 dihydrochalcone 
• 3412-44-0 1,3-diphenylpropene 
• 5209-18-7 cis-1,3-diphenylpropene 
• 3412-44-0 (1E)-1,3-diphenylpropene 
• 94-41-7 benzalacetophenone 
• 120-46-7 1,3-diphenylpropanedione 
• 109-70-6 1.3-chlorobromopropane 
• 71-43-2 benzene 
• 100-42-5 styrene 
• 108-88-3 toluene 
• 96-18-4 1,2,3-trichloropropane 
• 96-11-7 1,2,3-tribromopropane 

Downstream Products

• 70336-38-8 1,3-bis(4-chloromethylphenyl)propane 
• 1083-30-3 dihydrochalcone 
• 3178-24-3 1,1'-(1,3-propanediyl)biscyclohexane 
• 10368-11-3 1,3-bis-(4-nitro-phenyl)-propane 
• 335-19-3 hexafluoro-1,3-bis-undecafluorocyclohexyl-propane 
• 20176-53-8 1,3-bis(4-propionylphenyl)propane 
• 6337-58-2 4,4'-Trimethylenbisacetophenone 
• 67442-67-5 1,1'-(1,3-propanediyl)bis<(4-chloroacetyl)benzene> 
• 147862-38-2 6-Oxo-6-[4-(3-phenyl-propyl)-phenyl]-hexanoic acid ethyl ester 
• 147862-37-1 7-Oxo-7-[4-(3-phenyl-propyl)-phenyl]-heptanoic acid ethyl ester 
• 132101-09-8 1,3-bis<4-(2-carboxybenzoyl)phenyl>propane 
• 123716-21-2 1,3-bis(phenylsulfonylimino)-1,3-diphenylpropane 
• 123716-20-1 1,3-bis(phenylsulfonylamino)-1,3-diphenylpropane 
• 101443-92-9 1,3-bis(4-chloroformylphenyl)propane 

Relevant academic research and scientific papers

3-Acetoxyquinuclidine as Catalyst in Electron Donor-Acceptor Complex-Mediated Reactions Triggered by Visible Light

3-Acetoxyquinuclidine was found to act as a catalytic electron donor species in a variety of electron donor-acceptor complex-mediated reactions. Only substoichiometric amounts (10-25 mol %) were needed to trigger the desired reaction. The outcome could be tuned by selecting the nature of the formed radical to perform amino- and hydro-decarboxylation, dimerization, and cyclization reactions. Importantly, no external additives were needed in this reaction.

Indium(III)-catalyzed reductive monoalkylation of electron-rich benzenes with aliphatic carboxylic acids leading to arylalkane derivatives

Described herein is the reaction of electron-rich aromatic compounds with aliphatic carboxylic acids treated with a catalytic amount (5 mol-%) of InI3, 1,1,3,3-tetramethyldisiloxane (TMDS), and molecular iodine. The reductive monoalkylation occurs smoothly to produce the corresponding arylalkane derivatives.

ELECTRON TRANSFER ON CIS- AND TRANS-1,2-DIPHENYLCYCLOPROPANE: STEREOISOMERIZATION AND FORMATION OF 1,3-DIPHENYLPROPENE AND 1,3-DIPHENYLPROPANE

Reaction of cis- or trans-1,2-diphenylcyclopropane with Na/K leads to stereoisomerization and (after protonation) to 1,3-diphenylpropane and 1,3-diphenylpropene, the latter not being formed by H-migration.

Acceleration of CuI-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents using lithium chloride

In the presence of LiCl, CuI-catalyzed coupling reaction of R(alkyl)-X with Ar(aryl)MgBr at rt was completed within 2 h. Effective leaving groups X in R-X were Br, I, OTs, but not Cl. Grignard reagents ArMgBr with both standard and bulky Ar such as 2-MeC

Hydrodefluorination and other hydrodehalogenation of aliphatic carbon-halogen bonds using silylium catalysis

Trialkylsilylium cation equivalents partnered with halogenated carborane anions (such as Et3Si[HCB11H5Cl6]) function as efficient and long-lived catalysts for hydrodehalogenation of C-F, C-Cl, and C-Br bonds with trialkylsilanes as stoichiometric reagents. Only C(sp3)-halogen bonds undergo this reaction. The range of C-F bond-containing substrates that participate in this reaction is quite broad and includes simple alkyl fluorides, benzotrifluorides, and compounds with perfluoroalkyl groups attached to an aliphatic chain. However, CF4 has proven immune to this reaction. Hydrodechlorination was carried out with a series of alkyl chlorides and benzotrichlorides, and hydrodebromination was studied only with primary alkyl bromide substrates. Competitive experiments established a pronounced kinetic preference of the catalytic system for activation of a carbon-halogen bond of a lighter halide in primary alkyl halides. On the contrary, hydrodechlorination of C6F 5CCl3 proceeded much faster than hydrodefluorination of C6F5CF3 in one-pot experiments. A solid-state structure of Et3Si[HCB11H5Cl6] was determined by X-ray diffraction methods.

Copper-catalyzed cross-coupling reactions of non-activated primary, secondary or tertiary alkyl chlorides with phenylmagnesium bromide

Efficient copper-catalyzed cross-coupling reactions of non-activated alkyl chlorides, including primary, secondary, and tertiary alkyl chlorides, with phenyl Grignard reagents were achieved. Preparation of phenylmagnesium bromide in 2-methyltetrahydrofuran is critical for the success of the reaction. This protocol expands the synthetic toolbox for the construction of C[sbnd]C bonds of non-activated primary, secondary, and tertiary alkyl chlorides via copper-catalyzed cross-coupling.

A four-member ring hypervalent iodine radical

A four-member ring hypervalent iodine radical has been detected in the laser flash photolysis of 1,3-diiodo-1,3-diphenylpropane. This species absorbs at 320 nm, has a lifetime of ～9.5 μs in cyclohexane, and is not quenchable by oxygen. Excitation of this radical by means of laser-drop photolysis results the formation of trans-1,2-diphenylcyclopropane through concerted iodine extrusion.

Reductive decarboxylation of N-(acyloxy)phthalimides via redox-initiated radical chain mechanism

Highly efficient reductive decarboxylation of N-(acyloxy)phthalimides which are readily prepared from carboxylic acids was achieved by visible light irradiation using Ru(bpy)3Cl2 as a sensitizer in the presence of BNAH and t-BuSH via radical chain mechanism.

Lamp versus laser photolysis of 1,3-dichloro-1,3-diphenylpropane in cyclohexane. Direct observation of 1,3-diphenylpropenyl radical

Laser photolysis of the title compound leads to two-photon processes indicating the involvement of the 1,3-diphenylpropanediyl biradical (12) and the 1,3-diphenylallyl radical (10).

Iron pincer complexes as catalysts and intermediates in alkyl-aryl kumada coupling reactions

Iron-catalyzed alkyl-aryl Kumada coupling has developed into an efficient synthetic method, yet its mechanism remains vague. Here, we apply a bis(oxazolinylphenyl)amido pincer ligand (Bopa) to stabilize the catalytically active Fe center, resulting in isolation and characterization of well-defined iron complexes whose catalytic roles have been probed and confirmed. Reactivity studies of the iron complexes identify an Fe(II) "ate" complex, [Fe(Bopa-Ph)(Ph)2]-, as the active species for the oxidative addition of alkyl halide. Experiments using radical-probe substrates and DFT computations reveal a bimetallic and radical mechanism for the oxidative addition. The kinetics of the coupling of an alkyl iodide with PhMgCl suggests that formation of the "ate" complex, rather than oxidative addition, is the turnover-determining step. This work provides insights into iron-catalyzed cross-coupling reactions of alkyl halides.