40734-75-6

Upstream product

• 6974-12-5 1,4-dibromo-2-butene 
• 71290-63-6 benzenediazonium bromide 
• 106-99-0 buta-1,3-diene 
• 62-53-3 aniline 
• 300-57-2 allylbenzene 
• 106-95-6 allyl bromide 
• 6052-66-0 1-phenyl-3-buten-2-ol 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 821-06-7 (E)-1,4-dibromobutene 
• 100-58-3 phenylmagnesium bromide 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 54966-42-6 ethyl 3-benzylacrylate 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 574743-42-3 C₅₈H₉₀N₄O₁₅ 
• 155295-67-3 3-[(E)-2(R)-(cyclopropylmethyl)-1-oxo-6-phenyl-4-hexenyl]-4(S)-(phenylmethyl)-2-oxazolidinone 
• 511553-23-4 1-bromo-2,3-epoxy-4-phenylbutane 
• 861398-62-1 ethyl 3-iodo-4-{[(2E)-4-phenyl-but-2-enyl]oxy}benzoate 
• 1401467-08-0 (E)-diethyl 2-methyl-1-(4-phenylbut-2-enyloxy)prop-1-enylphosphonate 
• 1417719-40-4 C₁₅H₁₈O₃ 
• 1417719-47-1 (E)-methyl 2-diazo-6-phenylhex-4-enoate 
• 1417719-56-2 C₁₃H₁₄O₂ 
• 1452139-79-5 (E)-2-benzyl-1,6-diphenylhex-4-en-1-one 
• 1452139-87-5 (E)-2-methyl-1,6-diphenylhex-4-en-1-one 
• 1452138-86-1 (E)-2-methyl-8-phenyloct-6-en-3-one 
• 1452138-93-0 (E)-1-cyclopropyl-6-phenylhex-4-en-1-one 

Relevant academic research and scientific papers

Highly selective hydrosilylation of equilibrating allylic azides

The Pt-catalyzed hydrosilylation of equilibrating allylic azides is reported. The reaction provides only one out of four possible hydrosilylation products in good yields and with very high chemoselectivity (alk-1-enevs.alk-2-ene), regioselectivity (linearvs.branched), and excellent functional group tolerance.

Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs, USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.

Palladium catalyzed cyclizations of oxime esters with 1,2-disubstituted alkenes: Synthesis of dihydropyrroles

Pd-catalyzed cyclizations of oxime esters with 1,2-dialkylated alkenes provide an entry to chiral dihydropyrroles. Substrate and catalyst controlled strategies for selective product formation (vs alternative pyrroles) are outlined.

Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups. Copyright

Enantioselective iridium-catalyzed allylic arylation

We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.

High diversity on simple substrates: 1,4-dihalo-2-butenes and other difunctionalized allylic halides for copper-catalyzed SN2′ reactions

Enantioselective allylic alkylation with an organomagnesium reagent catalyzed by copper thiophene carboxylate (CuTC) was carried out on difunctionalized substrates, such as commercially available 1,4-dichloro-2- butene and 1,4-dibromo-2-butene, and on similar compounds of higher substitution pattern of the olefin for the formation of all-carbon chiral quaternary centers. The high regioselectivity obtained throughout the reactions favored good regiocontrol for the addition of phenyl Grignard reagents. Other difunctionalized substrates (allylic ethers and allylic alcohols) also underwent asymmetric SN2′ substitution.

A short synthesis of (+)-(S)-kurasoin B

A short efficient enantioselective synthesis leading directly to (+)-(S)-kurasoin B has been achieved in 5 steps and 25% overall yield from (2E)-ethyl-4-phenylbut-2-enoate using Sharpless asymmetric dihydroxylation and CH3NO2-assiste

Trimethyl phosphite as a trap for alkoxy radicals formed from the ring opening of oxiranylcarbinyl radicals. Conversion to alkenes. Mechanistic applications to the study of C-C versus C-O ring cleavage

Trimethyl phosphite, (MeO)3P, is introduced as an efficient and selective trap in oxiranylcarbinyl radical (2) systems, formed from haloepoxides 8-13 under thermal AIBN/n-Bu3SnH conditions at about 80 °C. Initially, the transformations of 8-13, in the absence of phosphite, to allyl alcohol 7 and/or vinyl ether 5 were measured quantitatively (Table 1). Structural variations in the intermediate oxiranylcarbinyl (2), allyloxy (3), and vinyloxycarbinyl (4) radicals involve influences of the thermodynamics and kinetics of the C-O (2 → 3, k1) and C-C (2 → 4, k2) radical scission processes and readily account for the changes in the amounts of product vinyl ether (5) and allyl alcohol (7) formed. Added (MeO)3P is inert to vinyloxycarbinyl radical 4 and selectively and rapidly traps allyloxy radical 3, diverting it to trimethyl phosphate and allyl radical 6. Allyl radicals (6) dimerize or are trapped by n-Bu3SnH to give alkenes, formed from haloepoxides 8, 9, and 13 in 69-95% yields. Intermediate vinyloxycarbinyl radicals (4), in the presence or absence of (MeO)3P, are trapped by n-Bu3SnH to give vinyl ethers (5). The concentrations of (MeO)3P and n-Bu3SnH were varied independently, and the amounts of phosphate, vinyl ether (5), and/or alkene from haloepoxides 10, 11, and 13 were carefully monitored. The results reflect readily understood influences of changes in the structures of radicals 2-4, particularly as they influence the C-O (k1) and C-C (k2) cleavages of intermediate oxiranylcarbinyl radical 2 and their reverse (k-1, k-2). Diversion by (MeO)3P of allyloxy radicals (3) from haloepoxides 11 and 12 fulfills a prior prediction that under conditions closer to kinetic control, products of C-O scission, not just those of C-C scission, may result. Thus, for oxiranylcarbinyl radicals from haloepoxides 11, 12, and 13, C-O scission (k1, 2 → 3) competes readily with C-C cleavage (k2, 2 → 4), even though C-C scission is favored thermodynamically.

New results on the functionalization of terminal alkenes by cross- metathesis reactions

The ruthenium-catalyzed reaction of allylbenzene with several types of alkene provides good yields of the cross-metathesis products regardless of the structural characteristics of the alkene.

Novel small renin inhibitors containing 4,5- or 3,5-Dihydroxy-2-substituted-6-phenylhexanamide replacements at the P2-P3 sites

Renin inhibitors containing a 4,5- or a 3,5-dihydroxy-2-substituted-6-phenylhexanamide fragment at the P2-P3 sites have been prepared and evaluated. The four possible diastereomeric diols of the two series of inhibitors were synthesi