106795-65-7

Usage

InChI:InChI=1/C13H15FO/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h4-5,8-10H,1-3,6-7H2

Upstream product

• 106795-61-3 2-(o-fluorophenyl)-1-oxaspiro<2,5>octane 
• 712-50-5 Cyclohexyl phenyl ketone 
• 446-52-6 2-Fluorobenzaldehyde 
• 106795-58-8 (o-fluorobenzyl)triphenylphosphonium chloride 
• 345-35-7 2-fluorobenzyl chloride 
• 106795-59-9 o-fluorophenyl(cyclohexylidene)methane 
• 82757-27-5 [(2-fluorophenyl)methylene]triphenylphosphorane 
• 108-94-1 cyclohexanone 

Downstream Products

• 1372151-89-7 C₁₇H₂₀O₂S 
• 1372151-93-3 C₁₅H₁₈OS 

Relevant academic research and scientific papers

Pd-Catalysed direct C(sp2)-H fluorination of aromatic ketones: Concise access to anacetrapib

The Pd-cataylsed direct ortho-C(sp2)-H fluorination of aromatic ketones has been developed for the first time. The reaction features good regioselectivity and simple operations, constituting an alternative shortcut to access fluorinated ketones. A concise synthesis of anacetrapib has also been achieved by using late-stage C-H fluorination as a key step.

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

The National Institutes of Health Molecular Libraries and Probe Production Centers Network (NIH-MLPCN) screened >300,000 compounds to evaluate their ability to restore fluconazole susceptibility in resistant Candida albicans isolates. Additional counter screens were incorporated to remove substances inherently toxic to either mammalian or fungal cells. A substituted indazole possessing the desired bioactivity profile was selected for further development, and initial investigation of structure-activity relationships led to the discovery of ML212.

Two New Oxindole Syntheses

Two oxindole syntheses are described, both starting from ketones, in which the carbonyl carbon becomes C-3 of the oxindole.The first route uses o-lithioformanilide followed by attack with cyanide ion and hydrolysis.The second uses a pinacol-type rearragement (or the γ-silyl alcohol variation) to create the quaternary centre, and involves an intramolecular displacement of fluoride ion from an unactivated benzene ring by an amide nitrogen to complete the lactam ring.The two routes are stereochemically complementary, giving different spiro-oxindoles from norbornanone.

TWO NEW STEREOCHEMICALLY COMPLEMENTARY OXINDOLE SYNTHESES

Two routes have been developed for the conversion of ketones to oxindoles in the general sense (3->4); with norbornanone, the two routes gave different oxindoles (22 and 24).

Some uses of silicon compounds in organic synthesis

1.The amount of γ-phenylthioalkylation of silyl dienol ethers is increased when the triphenylsilyl ether is used in place of the trimethylsilyl ether.Phenylthiomethylation is the least γ-selective carbon electrophile of several tried so far. 2.The acid-catalysed reactions of a range of γ-silyl tertiary alcohols cleanly give rearrangement, in which the silyl group controls the outcome.The reactions are similar in several respects to the rearrangements of the corresponding pinacols, except that the silicon controlled reactions are usually cleaner and give higher yields.The reaction is particularly useful for setting up quaternary carbon atoms.