462093-58-9

Upstream product

• 87666-40-8 ethyl (2E)-3-cyclohexyl-3-phenyl prop-2-enoate 
• 26482-44-0 3-cyclohexyl-3-phenyl-acrylic acid ethyl ester 
• 91140-23-7 ethyl 3,4,4-trimethylpent-2-enoate 
• 712-50-5 Cyclohexyl phenyl ketone 

Downstream Products

• 648425-31-4 (2E)-3-cyclohexyl-3-phenylprop-2-en-1-yl chloride 
• 462093-62-5 [(1E)-3-bromo-1-cyclohexylprop-1-enyl]benzene 
• 137542-86-0 (3R)-3-cyclohexyl-3-phenylpropanal 
• 149598-04-9 (+)-(2S,3S)-trans-3-cyclohexyl-3-phenyloxiranemethanol 
• 137542-88-2 (+)-(R)-3-cyclohexyl-3-phenylpropan-1-ol 
• 121314-51-0 (S)-3-cyclohexyl-3-phenylpropan-1-ol 
• 1613507-31-5 (S,E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene 
• 196302-63-3 (E)-(3-cyclohexylprop-1-ene-1,3-diyl)dibenzene 

Relevant academic research and scientific papers

Selective Synthesis of Z-Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light-Promoted Photocatalytic E to Z Isomerization

A photocatalytic E to Z isomerization of alkenes using an iridium photosensitizer under mild reaction conditions is disclosed. This method provides scalable and efficient access to Z-cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity. Importantly, this method also provides a powerful strategy for the selective synthesis of Z-magnolol and honokiol derivatives possessing potential biological activity.

Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols Using MaxPHOX Ligands: Experimental and Theoretical Study

The asymmetric isomerization of primary allylic alcohols to chiral aldehydes using iridium-catalysts bearing P,N-MaxPHOX ligands has been studied. These catalysts can be fine-tuned as they present three different stereogenic centers to modulate both the reactivity and enantioselectivity of a family of different substrates. The experimental part is supported by a DFT study of the reaction mechanism, which provides new insights into the key steps of this transformation.

Iridium-catalyzed asymmetric hydrogenation of 3,3-disubstituted allylic alcohols in ethereal solvents

Ir-phosphinomethyl-oxazoline complexes have been identified as efficient, highly enantioselective catalysts for the asymmetric hydrogenation of 3,3-disubstituted allylic alcohols and related homoallylic alcohols. In contrast to other N,P ligand complexes, which require weakly coordinating solvents, such as dichloromethane, these catalysts perform well in more ecofriendly THF or 2-MeTHF. Their synthetic potential was demonstrated with the formal total synthesis of four bisabolane sesquiterpenes. Particularly high enantioselectivity values in the asymmetric hydrogenation of 3,3-disubstituted allylic alcohols and related homoallylic alcohols have been achieved with Ir-phosphinomethyloxazoline catalysts. In contrast to other N,P-ligand complexes, which require weakly coordinating solvents, such as CH 2Cl2, these catalysts perform well in more ecofriendly THF or 2-MeTHF (see scheme; CODa =a 1,5-cyclooctadiene). Copyright

Highly enantioselective asymmetric isomerization of primary allylic alcohols with an iridium-N,P complex

Access to chiral aldehydes: The asymmetric isomerization of primary allylic alcohols was studied with a bicyclic phosphine-oxazoline iridium catalyst. This method displays a broad substrate scope and leads to the desired chiral aldehydes with excellent enantioselectivities (see scheme; R1, R 2=Ar or alkyl). Copyright

Improved catalysts for the iridium-catalyzed asymmetric isomerization of primary allylic alcohols based on charton analysis

An improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air-stable complexes relied on the preliminary mechanistic information available, and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation. Sterically unbiased chiral aldehydes that were not accessible previously have been obtained with high levels of enantioselectivity, thus validating the initial hypothesis regarding the selected ligand-design elements. A rationale for the high enantioselectivities achieved in most cases is also presented. Achieving enantioselectivity: An improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air-stable complexes relies on preliminary mechanistic information and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation (see figure).

Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception

Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.12,5]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.03,8]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains,

N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as μ-opioid receptor agonists. Effects on μ-affinity of arylalkenyl chain modifications

Two series of N-3-arylpropenyl-N-9-propionyl-3,9-diazabicyclo[3.3.1]nonanes (1b-j) and of the reverted N-3-propionyl-N-9-arylpropenyl isomers (2b-j) as analogues of the previously reported analgesic N-3(9)-cinnamyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes (DBN) (1a, 2a) were synthesised and their affinity and selectivity towards opioid μ-, δ- and κ-receptors were evaluated. Several compounds (1e,i,j-2d,e,f,g,j) exhibited a μ-affinity in the low nanomolar range with moderate or negligible affinity towards δ- and κ-receptors. The representative term N-9-(3,3-diphenylprop-2-enyl)-N-3-propionyl-DBN (2d) displayed in vivo (mouse) a potent analgesic effect (ED50 3.88 mg/kg ip) which favourably compared with that of morphine (ED50 5 mg/kg ip). In addition, 2d produced in mice tolerance after a period twice as long with morphine.