37904-38-4

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 107-02-8 acrolein 
• 1075-74-7 5-phenylpent-1-ene 
• 104-53-0 3-phenyl-propionaldehyde 
• 1826-67-1 vinyl magnesium bromide 
• 63922-69-0 (2-trimethylsilylethylidene)triphenylphosphorane 
• 103-63-9 1-phenyl-2-bromoethane 
• 166672-25-9 Allyl-dimethyl-(1-phenylsulfanyl-cyclopropyl)-silane 
• 3536-96-7 vinylmagnesium chloride 
• 1206535-31-0 1-phenethylallyl 2-bromo-2-methyl-propanoic acid ester 
• 125541-71-1 Methanesulfonic acid (S)-1-(R)-oxiranyl-3-phenyl-propyl ester 
• 2181-42-2 trimethylsulphonium iodide 
• 141036-66-0 (R)-(2-phenylethyl)oxirane 
• 1000376-25-9 (S)-4,4,5,5-tetramethyl-2-[5-phenyl-1-penten-3-yl]-1,3,2-dioxaborolane 

Downstream Products

• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 122016-56-2 1-Methyl-4-(1-phenethyl-allyloxymethanesulfonyl)-benzene 
• 20795-51-1 1-phenylpentan-3-one 
• 138662-34-7 (S)-1-(R)-Oxiranyl-3-phenyl-propan-1-ol 
• 169298-79-7 3-Azidocarbonyloxy-5-phenyl-1-pentene 
• 181180-61-0 (R)-(-)-3-acetoxy-5-phenylpent-1-ene 
• 1745-16-0 (E)-3-pentenylbenzene 
• 16487-65-3 (Z)-1-phenyl-3-pentene 
• 37904-38-4 (3S)-5-phenyl-1-penten-3-ol 
• 139951-60-3 C₁₉H₂₁NO₄S 
• 220432-14-4 5-phenyl-1-penten-3-yl chlorodifluoroacetate 
• 165074-30-6 5-phenyl-1-penten-3-yl bromodifluoroacetate 
• 145451-76-9 4-(Phenylmethyl)hept-6-en-3-one 
• 145451-75-8 4-Methyl-1-phenylhept-6-en-3-one 

Relevant academic research and scientific papers

An efficient chemoenzymatic approach towards the synthesis of rugulactone

Rugulactone is a natural product isolated from the plant Cryptocarya rugulosa. It has shown very important biological activity as an inhibitor of the nuclear factor κB (NF-κB) activation pathway. A new chemoenzymatic approach towards the synthesis of rugu

Regio- And Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines

Robust air-stable cyclometalated π-allyliridium C,O-benzoates modified by (S)-tol-BINAP catalyze the reaction of secondary aliphatic amines with racemic alkyl-substituted allylic acetates to furnish products of allylic amination with high levels of enantioselectivity. Complete branched regioselectivities were observed despite the formation of more highly substituted C-N bonds.

Synthesis of Bioactive Diarylheptanoids from Alpinia officinarum and Their Mechanism of Action for Anticancer Properties in Breast Cancer Cells

An efficient synthesis of the Alpinia officinarum-derived diarylheptanoids, viz., enantiomers of a β-hydroxyketone (1) and an α,β-unsaturated ketone (2) was developed starting from commercially available eugenol. Among these, compound 2 showed a superior

Selective hydroboration of equilibrating allylic azides

The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.

GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington's Disease-Related Phenotypes

GPR52 is an orphan G protein-coupled receptor (GPCR) that has been recently implicated as a potential drug target of Huntington's disease (HD), an incurable monogenic neurodegenerative disorder. In this research, we found that striatal knockdown of GPR52 reduces mHTT levels in adult HdhQ140 mice, validating GPR52 as an HD target. In addition, we discovered a highly potent and specific GPR52 antagonist Comp-43 with an IC50 value of 0.63 μM by a structure-activity relationship (SAR) study. Further studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead compound for further investigation.

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

Synthesis of β-hydroxyenones and its application toward development of tetrahydro-4H-pyran-4-one in an atom-economic fashion is limited. This manuscript describes a ruthenium-catalyzed atom-economic coupling of pent-2-yne-1,5-diols and Michael acceptors as an efficient route for the synthesis of β-hydroxyenones with excellent yields and high regioselectivity. The β-hydroxyenones further undergo a 6-endo trig cyclization under acid-catalyzed conditions to deliver the tetrahydro-4H-pyran-4-ones with high diastereoselectivity. An intramolecular aldol condensation under mild basic conditions and palladium-catalyzed oxidative aromatization was developed for the synthesis of hexahydro-6H-isochromen-6-ones and isochromanols, respectively, from highly substituted tetrahydro-4H-pyran-4-ones with excellent yield and diastereoselectivity. Overall, this work demonstrates the synthetic potential toward the synthesis of oxacycles like tetrahydro-4H-pyran-4-ones, hexahydro-6H-isochromen-6-ones, and isochromanols via an atom-economic catalysis.

Concise, scalable and enantioselective total synthesis of prostaglandins

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]

Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism

One of the most oft-employed methods for C-C bond formation involving the coupling of vinyl-halides with aldehydes catalyzed by Ni and Cr (Nozaki-Hiyama-Kishi, NHK) has been rendered more practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK can even enable non-canonical substrate classes, such as redox-active esters, to participate with low loadings of Cr when conventional chemical techniques fail. A combination of detailed kinetics, cyclic voltammetry, and in situ UV-vis spectroelectrochemistry of these processes illuminates the subtle features of this mechanistically intricate process.

Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes

A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.