76024-91-4

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4648-54-8 trimethylsilylazide 
• 21040-45-9 Cinnamyl acetate 
• 82859-39-0 trans-cinnamyl iodide 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 28664-25-7 (2E)-3-phenylprop-2-en-1-yl trifluoroacetate 
• 39199-93-4 (Z)-(3-chloroprop-1-en-1-yl)benzene 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 160879-62-9 methyl 1-phenylprop-2-enyl carbonate 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 104-54-1 3-Phenylpropenol 
• 100-52-7 benzaldehyde 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4192-77-2 ethyl cinnamate 

Downstream Products

• 4360-51-4 cinnamylamine 
• 4335-60-8 (E)-cinnamylamine 
• 120990-23-0 N-(phenylmethylidene)-N-[(E)-3-phenylprop-2-enyl]amine 
• 120990-24-1 (E)-3-Acetamido-1-phenylprop-1-ene 
• 136844-01-4 2,2,3-Triphenyl-pent-4-enenitrile 
• 151231-67-3 (N-cinnamylimino)triphenylphosphorane 
• 147410-39-7 N-tert-butoxycarbonyloxy-3-phenylpropylamine 
• 15023-38-8 (2E)-N,N-dimethyl-N'-(3-phenyl-allylidene)-hydrazine 
• 622-79-7 benzyl azide 
• 1158998-63-0 1-(3-phenyl-2-propenyl)-4-phenyl-1,2,3-triazole 
• 474055-66-8 ((E)-3-isothiocyanatoprop-1-enyl)benzene 
• 842172-35-4 [1-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(E)-ylidene]-((E)-3-phenyl-allyl)-amine 

Relevant academic research and scientific papers

Interrupted CuAAC-Thiolation for the Construction of 1,2,3-Triazole-Fused Eight-Membered Heterocycles from O-/N-Propargyl derived Benzyl Thiosulfonates with Organic Azides

A copper(I)-catalyzed interrupted click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles in 61–74% yields. From a synthetic point of view, the present protocol has been demonstrated at gram-scale reactions. A plausible mechanism is also proposed based on experimental results and control experiments. (Figure presented.).

Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3

Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.

Further investigation of harmicines as novel antiplasmodial agents: Synthesis, structure-activity relationship and insight into the mechanism of action

The rise of the resistance of the malaria parasite to the currently approved therapy urges the discovery and development of new efficient agents. Previously we have demonstrated that harmicines, hybrid compounds composed from β-carboline alkaloid harmine

Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis

Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

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.

Reduction of α,β-unsaturated nitroolefins into nitroalkanes with Hantzsch ester promoted by isothiouronium salts

α,β-Unsaturated nitroolefins were reduced into nitroalkanes with a Hantzsch ester, promoted by S-benzyl isothiouronium iodide. The reactions proceeded successfully to afford the desired products in high yields and with excellent chemoselectivity.

Organocatalytic Synthesis of Oxazolines and Dihydrooxazines from Allyl-Amides: Bypassing the Inherent Regioselectivity of the Cyclization

A selective and efficient methodology for the construction of either oxazolines or dihydrooxazines from the corresponding allyl-amides is reported. Bypassing the inherent selectivity of the cyclization and depending on the substitution pattern of the substrate, a selective epoxidation-cyclization was developed leading to either the five-membered or the six-membered ring, upon simple and complementary reaction conditions. The cyclization products were obtained in good to excellent yields and high selectivities. (Figure presented.).

Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry

The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best APN inhibition with an IC50 value of 0.089 ± 0.007 μM, which was two orders of magnitude lower than that of bestatin (IC50 = 9.4 ± 0.5 μM). Compound 13v also showed dose-dependent anti-angiogenesis activities. Even at the lower concentration (10 μM), compound 13v presented similar anti-angiogenesis activity compared with bestatin at 100 μM in both the human umbilical vein endothelial cells (HUVECs) capillary tube formation assay and the rat thoracic aorta rings test. Moreover, compared with bestatin, 13v exhibited comparable, if not better in vivo anti-metastasis activity in a mouse H22 pulmonary metastasis model.

Sustainable organophosphorus-catalysed Staudinger reduction

A highly efficient and sustainable catalytic Staudinger reduction for the conversion of organic azides to amines in excellent yields has been developed. The reaction displays excellent functional group tolerance to functionalities that are otherwise prone to reduction, such as sulfones, esters, amides, ketones, nitriles, alkenes, and benzyl ethers. The green nature of the reaction is exemplified by the use of PMHS, CPME, and a lack of column chromatography.

Practical regio- and stereoselective azidation and amination of terminal alkenes

There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.