7332-01-6

Upstream product

• 13633-25-5 1-Bromo-4-phenylbutane 
• 3360-41-6 4-phenyl-butan-1-ol 
• 64283-87-0 4-phenyl-1-iodobutane 
• 768-56-9 4-Phenylbut-1-ene 
• 2270-20-4 5-Phenylpentanoic acid 

Downstream Products

• 1316650-41-5 C₁₇H₁₈N₄O₂S 
• 1316649-95-2 C₁₉H₂₀N₄O₂ 
• 154874-88-1 (±)-tert-butyl-2-phenylpyrrolidine-1-carboxylate 
• 13214-66-9 4-phenyl-1-butylamine 
• 1076199-53-5 2-pyridin-3-ylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 700-91-4 2-phenyl-1-pyrroline 
• 2046-18-6 4-phenylbutyronitrile 
• 174311-02-5 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 174310-75-9 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 1006-64-0 2-(phenyl)pyrrolidine 

Relevant academic research and scientific papers

An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides

The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is

A click-based modular approach to introduction of peroxides onto molecules and nanostructures

Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials. Dialkyl peroxide-substituted alkynes undergo Cu(i)-promoted reaction with azides in either organic or biphas

Iodine(III) reagent (ABX—N3)-induced intermolecular anti-Markovnikov hydroazidation of unactivated alkenes

Anti-Markovnikov hydroazidation of unactivated alkenes using ABX2014;N3 as an initiator has been developed at room temperature, wherein hydrogen azide (HN3) acts as both hydrogen and azidating agent. Notably, the HN3 reage

Optimal Destabilization of DNA Double Strands by Single-Nucleobase Caging

Photolabile protecting groups are widely used to trigger oligonucleotide activity. The ON/OFF-amplitude is a critical parameter. An experimental setup has been developed to identify protecting group derivatives with superior caging properties. Bulky rests

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

Dehydroxylation of alcohols for nucleophilic substitution

The Ph3P/ICH2CH2I system-promoted dehydroxylative substitution of alcohols was achieved to construct C-O, C-N, C-S and C-X (X = Cl, Br, and I) bonds. Compared with the previous approaches such as the Appel reaction and Mitsunobu reaction, this protocol offers some practical advantages such as safe operation and a convenient amination process.

Catalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation

Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.

A Multidimensional Diversity-Oriented Synthesis Strategy for Structurally Diverse and Complex Macrocycles

Synthetic macrocycles are an attractive area in drug discovery. However, their use has been hindered by a lack of versatile platforms for the generation of structurally (and thus shape) diverse macrocycle libraries. Herein, we describe a new concept in library synthesis, termed multidimensional diversity-oriented synthesis, and its application towards macrocycles. This enabled the step-efficient generation of a library of 45 novel, structurally diverse, and highly-functionalized macrocycles based around a broad range of scaffolds and incorporating a wide variety of biologically relevant structural motifs. The synthesis strategy exploited the diverse reactivity of aza-ylides and imines, and featured eight different macrocyclization methods, two of which were novel. Computational analyses reveal a broad coverage of molecular shape space by the library and provides insight into how the various diversity-generating steps of the synthesis strategy impact on molecular shape.

Direct C-H amination of arenes with alkyl azides under rhodium catalysis

New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C-H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones. Copyright

Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries

To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.