339177-03-6

Upstream product

• 195969-54-1 methyl 3-(2-vinylphenyl)propanoate 
• 1196708-20-9 C₁₇H₂₈OSi 
• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 75927-49-0 pinacol vinylboronate 
• 66191-86-4 3-(2-bromophenyl)propanoic acid,methyl ester 
• 136863-23-5 3-[2-(hydroxymethyl)phenyl]propan-1-ol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 25705-34-4 2-(2-oxoethyl)benzaldehyde 
• 63969-79-9 2-(3'-oxy-3'-methoxypropyl)benzaldehyde 
• 447-53-0 1,2-Dihydronaphthalene 
• 148433-03-8 2-(3-Hydroxypropyl)benzaldehyde 
• 163277-65-4 3-(2-vinylphenyl)acrylic acid methyl ester 
• 2039-88-5 2-bromostyrene 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 339177-04-7 3-(2-ethenylphenyl)propionaldehyde 
• 1196708-21-0 C₁₁H₁₃Br 
• 874334-13-1 C₃₁H₄₄N₄O₃ 
• 874332-88-4 C₃₁H₄₂N₄O₃ 
• 874334-14-2 C₃₂H₄₄N₄O₃ 
• 339177-08-1 (E)-5-(2-ethenylphenyl)-1-phenylpent-2-en-1-ol 
• 339177-05-8 methyl (E)-5-(2-ethenylphenyl)pent-2-enoate 
• 339177-06-9 (E)-5-(2-ethenylphenyl)pent-2-en-1-ol 
• 339177-07-0 (E)-5-(2-ethenylphenyl)pent-2-enal 
• 401916-96-9 toluene-4-sulfonic acid 1-[2-(2-vinylphenyl)ethyl]pentyl ester 
• 401917-03-1 toluene-4-sulfonic acid 2-methyl-1-[2-(2-vinylphenyl)ethyl]propyl ester 
• 401917-48-4 1-(2-vinylphenyl)heptan-3-ol 
• 401917-52-0 4-methyl-1-(2-vinylphenyl)pentan-3-ol 

Relevant academic research and scientific papers

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-ric

Organocatalytic Access to a cis-Cyclopentyl-γ-amino Acid: An Intriguing Model of Selectivity and Formation of a Stable 10/12-Helix from the Corresponding γ/α-Peptide

In this study, we have developed a highly enantioselective organocatalytic route to the (1S,2R)-2-(aminomethyl)cyclopentane-1-carboxylic acid monomer precursor, which has a cis-configuration between the C- and N-termini around the cyclopentane core. Kinet

Macrocyclic Modulators of the Ghrelin Receptor

The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (Part I): Development of ulimorelin (TZP-101) from Hit to Clinic

High-throughput screening of Tranzyme Phar-ma's proprietary macrocycle library using the aequorin Ca2+-bioluminescence assay against the human ghrelin receptor (GRLN) led to the discovery of novel agonists against this G-protein coupled receptor. Early hits such as 1 (Ki = 86 nM, EC50 = 134 nM) though potent in vitro displayed poor pharmacokinetic properties that required optimization. While such macrocycles are not fully rule-of-five compliant, principally due to their molecular weight and clogP, optimization of their pharmacokinetic properties proved feasible largely through conformational rigidification. Extensive SAR led to the identification of 2 (Ki = 16 nM, EC50 = 29 nM), also known as ulimorelin or TZP-101, which has progressed to phase III human clinical trials for the treatment of postoperative ileus. X-ray structure and detailed NMR studies indicated a rigid peptidomimetic portion in 2 that is best defined as a nonideal type-I′ β-turn. Compound 2 is 24% orally bioavailable in both rats and monkeys. Despite its potency, in vitro and in gastric emptying studies, 2 did not induce growth hormone (GH) release in rats, thus demarcating the GH versus GI pharmacology of GRLN. (Figure presented)

Silicon- and sulfur-mediated synthesis of benzoannulated cyclooctanols

The reaction of a silyl-substituted thioacetal with ortho-difunctionalized benzenes as biselectrophiles allows access to multifunctional cyclooctanols.

Discovery of a new class of macrocyclic antagonists to the human motilin receptor

A novel class of macrocyclic peptidomimetics was identified and optimized as potent antagonists to the human motilin receptor (hMOT-R). Well-defined structure-activity relationships allowed for rapid optimization of potency that eventually led to high aff

Preparation of oxocanes by electrophilic cyclizations of unsaturated alcohols in the presence of bis(collidine)halonium(I) hexafluorophosphates

7-Octen-1-ols substituted in the sp3-sp3 carbon chain with carbocyclic (phenyl and cyclopropane) and heterocyclic (epoxide and dioxolane) moieties were prepared and their cyclizations in the presence of bis(collidine)iodonium(I) and-bromonium(I) hexafluorophosphates as electrophiles were studied. Oxocanes were obtained in modest to good yields when a rigid cyclic moiety (cyclopropane or phenyl) was present in the chain, while yields of cyclizations were lower if the cyclic component had a certain flexibility (dioxolane). Low yields were obtained with substrates bearing an epoxide substituent, probably because of stability problems due to the presence of collidine. With the vinylcyclopropane alcohol 12 we observed mainly the opening of the cyclopropane ring and the cyclization produced a tetrahydropyran derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Olefins turned alkylating agents: Diastereoselective intramolecular Zr-catalyzed olefin alkylations

(Equation Presented) 62% yield; 12 : 1 syn : anti The first examples of intramolecular Zr-catalyzed electrophilic alkylation of aryl olefins are disclosed. Substituted carbo-and heterocycles are prepared efficiently and diastereoselectively.

Some observations concerning the thermally induced oxy-ene reaction

Several examples of thermally induced intramolecular oxy-ene reactions leading to six- or five-membered rings are reported. The yields vary from poor to good, depending on the thermal lability of the substrate. Considering the high temperatures required t