39110-26-4

Upstream product

• 603-35-0 triphenylphosphine 
• 637-59-2 1-Bromo-3-phenylpropane 
• 5717-39-5 bromotriphenyl(3-phenylpropyl)-λ⁵-phosphane 
• 7484-37-9 (3-phenylpropyl)triphenylphosphonium bromide 
• 47562-49-2 <3-Phenyl-propyl>-triphenyl-phosphonium 

Downstream Products

• 122982-78-9 1-((Z)-4-Phenyl-1-trifluoromethyl-but-1-enyl)-piperidine 
• 122982-79-0 1-((E)-4-Phenyl-1-trifluoromethyl-but-1-enyl)-piperidine 
• 122982-78-9 1-((E)-4-Phenyl-1-trifluoromethyl-but-1-enyl)-piperidine 
• 122977-65-5 trifluoro-1,1,1 trimethylsilyloxy-2 phenyl-5 pentene-2 
• 122982-86-9 Dibenzyl-((Z)-4-phenyl-1-trifluoromethyl-but-1-enyl)-amine 
• 122982-87-0 Dibenzyl-((E)-4-phenyl-1-trifluoromethyl-but-1-enyl)-amine 
• 122982-86-9 Dibenzyl-((E)-4-phenyl-1-trifluoromethyl-but-1-enyl)-amine 
• 23055-11-0 1,6-diphenylhex-3-ene 
• 1124258-45-2 C₂₄H₃₄OSi 
• 14853-15-7 [1-(Bis-ethylsulfanyl-methylene)-3-phenyl-propyl]-triphenyl-phosphonium; iodide 
• 14063-60-6 4-Phenyl-2-(triphenyl-λ⁵-phosphanylidene)-dithiobutyric acid ethyl ester 
• 133626-02-5 (Z)-(R)-N-Boc-2-amino-6-phenyl-3-hexenol 
• 122982-98-3 4-(1,1,1-trifluoro-5-phenylpentan-2-yl)morpholine 
• 122983-00-0 1-(1,1,1-trifluoro-5-phenylpentan-2-yl)piperidine 

Relevant academic research and scientific papers

Heavier Carbonyl Olefination: The Sila-Wittig Reaction

The Wittig reaction is one of the most versatile tools in the repertoire of organic chemists. Thus, a broad variety of carbonyl compounds can be converted to tailor-made alkenes with phosphorus ylides under mild conditions. However, no comparable reaction has been reported for silanones, the silicon congeners of ketones. Here, we demonstrate for the first time the successful application of the Wittig olefination to iminosilylsilanone 1. The selective formation of a series of silenes (R2Sia? CR2) via the sila-Wittig reaction revealed an unprecedented approach to otherwise elusive compounds. In addition, the highly reactive and zwitterionic nature of 1 was also susceptible to nucleophilic attacks and cycloaddition reactions by and with the phosphorus ylides. Our results therefore make another important contribution to discovering the differences and similarities between carbon and silicon.

Synthesis of indoles via alkylidenation of acyl hydrazides

Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.

Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues

The synthesis of a series of brominated cross-conjugated dienones, marine prostanoid analogues, was considered using two cyclopentannelation processes, from enamine (by a domino 3-aza Claisen/Mannich reaction) and from dioxolane ester alkylation followed by intramolecular Wittig reaction. All the compounds synthesized featured the same cross-conjugated dienone system, with a vicinal syn or anti diol on the ω-chain. The replacement of the ω-side-chain of the natural prostanoids with a 1-hydroxyphenyl-butyl moiety gave new prostanoids (32-34) with good cytotoxicities. In a second series of products, the possibility of a shorter α-side-chain bearing a simple phenyl ester was investigated. The results indicated a dramatic increase in the cytotoxicity (39, 40, 43, 44). Finally, in a third series, the ω- 1-hydroxyphenyl-butyl was replaced by a 1-hydroxymethyloxybenzyl chain. These simpler compounds (45,46,47,48, 60) are still highly cytotoxic, in the medium range of 60 nM, close to the value of natural punaglandins.

Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions

The insertion reaction of alkylidene carbenes is demonstrated to be an effective method for the synthesis of 2,5-dihydrofuran ring systems. The best results have been obtained on substrates containing electron-withdrawing substituents, which appear less prone to the competing rearrangement reaction. This insight has led to the development of a new method for the synthesis of the core structure of the squalestatin-zaragozic acid natural products.

Amide Bond Replacements Incorporated into CCK-B Selective "Dipeptoids"

This paper describes the chemical synthesis and CCK-B and CCK-A receptor binding affinities of a series of compounds in which the central amide bond of the CCK-B "dipeptoid" ligand tricyclo3,7>dec-2-yl-21-(hydroxymethyl)-2

Synthesis of Chiral Vinylglycines

(R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8.Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (>95percent ee) and double-bond geometry.D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives β,γ-unsaturated amino acids with the L configuration.The double-bond geometry is controlled by the nature of the phosphorous ylide employed.The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

NOUVELLE SYNTHESE DE TRIFLUOROMETHYLCETONES ET D' α-BROMO TRIFLUOROMETHYLCETONES

We report a new method for the preparation of trifluoromethylketones, as an alternative to the use of organometallics.The condensation of phosphonium ylides with trimethylsilyl trifluoroacetate provides silyloxy enol ethers whose hydrolysis leads to trifluoromethylketones.Bromation of the same silyloxy enol ether is also a convenient preparation of α-bromo trifluoromethylketone.