29805-49-0

Upstream product

• 67-56-1 methanol 
• 6540-96-1 2-benzyl-4-pentenoic acid 
• 107-18-6 allyl alcohol 
• 501-52-0 3-Phenylpropionic acid 
• 100-39-0 benzyl bromide 
• 40637-56-7 dimethyl allylmalonate 
• 154194-01-1 methyl (E)-2-benzyl-5-trimethylsilyl-4-pentenoate 
• 145429-73-8 2-allyl-2-benzylmalonic acid dimethyl ester 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 106-95-6 allyl bromide 
• 138536-59-1 methyl (Z)-2-benzyl-5-iodo-4-pentenoate 

Downstream Products

• 130450-11-2 2-Benzyl-4,4-dimethoxy-butyric acid methyl ester 
• 247064-72-8 C₁₅H₁₈O 
• 1356461-22-7 6-benzyl-1,8-nonadiene-3-yn-5-ol 
• 1356451-17-6 methyl 6-benzyl-1,8-nonadiene-3-yn-5-yl carbonate 
• 1356461-20-5 4-benzylhept-6-en-1-yn-3-ol 
• 205373-43-9 2-Benzyl-4-fluoro-pent-4-enoic acid methyl ester 
• 205373-54-2 2-benzyl-4-fluoro-4-pentenoic acid 
• 205373-51-9 2,2-Dimethyl-propionic acid 2-benzyl-4-fluoro-pent-4-enyl ester 
• 205373-46-2 2,2-Dimethyl-propionic acid 2-benzyl-pent-4-enyl ester 
• 205373-67-7 2-benzyl-4-fluoro-4-pentenol 

Relevant academic research and scientific papers

Stereoselective [3,3]-sigmatropic rearrangement promoted by the metal [1,3]-shift of binuclear fischer carbene complexes

(Chemical Equation Presented) Reaction of chiral homobinuclear Fischer chromium carbene complexes with allyl alcohol in the presence of NaH and the following oxidative demetalation gave α-allyl esters in up to 97% ee via [3,3]-sigmatropic rearrangement reaction promoted by the metal 1,3-shift. On the other hand, chiral heterobinuclear tungsten carbene complexes with arene chromium complexes afforded α-allyl-β-hydroxy esters as a major product in up to 92/8 dr by the same reaction sequence.

Isomerization of olefins triggered by rhodium-catalyzed C-H bond activation: Control of endocyclic β-hydrogen elimination

Five-membered metallacycles are typically reluctant to undergo endocyclic β-hydrogen elimination. The rhodium-catalyzed isomerization of 4-pentenals into 3-pentenals occurs through this elementary step and cleavage of two C-H bonds, as supported by deuterium-labeling studies. The reaction proceeds without decarbonylation, leads to trans olefins exclusively, and tolerates other olefins normally prone to isomerization. Endocyclic β-hydrogen elimination can also be controlled in an enantiodivergent reaction on a racemic mixture.

Diastereoselective carbocyclization of 1,6-heptadienes triggered by rhodium-catalyzed activation of an olefinic C-H bond

The use of α,ω-dienes as functionalization reagents for olefinic carbon-hydrogen bonds has been rarely studied. Reported herein is the rhodium(I)-catalyzed rearrangement of prochiral 1,6-heptadienes into [2,2,1]-cycloheptane derivatives with concomitant creation of at least three stereogenic centers and complete diastereocontrol. Deuterium-labeling studies and the isolation of a key intermediate are consistent with a group-directed C-H bond activation, followed by two consecutive migratory insertions, with only the latter step being diastereoselective. Folding alkenes: Described is the first example of a rhodium(I)-catalyzed functionalization of an olefinic C-H bond with a 1,6-heptadiene reagent. This carbocyclization is completely diastereoselective and creates at least three stereogenic centers from simple prochiral substrates. The directing group can easily be converted into other functional groups.

Combined dealkoxycarbonylation and lactonisation of unsaturated malonates in ionic liquids

Heating unsaturated malonates with LiCl and water in [bmim][Br] or [bmim][BF4]/[bmim][Br] produces unsaturated esters or lactones, respectively.

GAMMA-AMINOAMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of the formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R11, R12, W, X, and n are defined herein, which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

Discovery of 4-Substituted Pyrrolidone Butanamides as New Agents with Significant Antiepileptic Activity

(S)-α-ethyl-2-oxopyrrolidine acetamide 2 (levetiracetam, Keppra, UCB S.A.), a structural analogue of piracetam, has recently been approved as an add-on treatment of refractory partial onset seizures in adults. This drug appears to combine significant efficacy and high tolerability due to a unique mechanism of action. The latter relates to a brain-specific binding site for 2 (LBS for levetiracetam binding site) that probably plays a major role in its antiepileptic properties. Using this novel molecular target, we initiated a drug-discovery program searching for ligands with significant affinity to LBS with the aim to characterize their therapeutic potential in epilepsy and other central nervous system diseases. We systematically investigated the various positions of the pyrrolidone acetamide scaffold. We found that (i) the carboxamide moiety on 2 is essential for affinity; (ii) among 100 different side chains, the preferred substitution α to the carboxamide is an ethyl group with the (S)-configuration; (iii) the 2-oxopyrrolidine ring is preferred over piperidine analogues or acyclic compounds; (iv) substitution of positions 3 or 5 of the lactam ring decreases the LBS affinity; and (v) 4-substitution of the lactam ring by small hydrophobic groups improves the in vitro and in vivo potency. Six interesting candidates substituted in the 4-position have been shown to be more potent antiseizure agents in vivo than 2. Further pharmacological studies from our group led to the selection of (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide 83α (ucb 34714) as the most interesting candidate. It is approximately 10 times more potent than 2 as an antiseizure agent in audiogenic seizure-prone mice. A clinical phase I program has been successfully concluded and 83α will commence several phase II trials during 2003.

A novel type of structurally simple nonpeptide inhibitors for α- chymotrypsin. Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket

Unexpectedly, methyl and benzyl esters of 2-allyl-3-benzenepropanoic acid were found to be not substrates but potent competitive inhibitors for α-chymotrypsin. The inhibitory property of the structurally simple nonpeptidic compounds is ascribed to their high binding affinity to the enzyme at the S2 rather than S1 subsite pocket. These inhibitors exist in a flexible form in solution, but as they bind to the enzyme bulky contrained conformers present in a minute concentration play an important role, forming tighter enzyme-inhibitor complexes by binding to the large hydrophobic S2 pocket. The contrained conformers are thought to be resulted from intramolecular CH/π interactions between a vinylic proton and the aromatic π-electron cloud in the inhibitor molecules. These compounds constitute novel examples of the induced-fit binding inhibitor of possibly simplest structure.

Utilization of Bu3SnSiMe3 in organic synthesis II. New cyclization by a stannyl anion generated from Bu3SnSiMe3 and R4NX

A new cyclization reaction of an aryl or vinyl halide bearing a carbonyl group such as ketone or ester has been developed by use of a stannyl anion generated in DMF from Bu3SnSiMe3 and Bu4NCl.Key words: Trimethylsilyl; Stannyl anion