152876-60-3

Upstream product

• 2216-94-6 phenylpropynoic acid ethyl ester 
• 541-41-3 chloroformic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 64-17-5 ethanol 
• 1184-76-5 difluorodiiodomethane 

Downstream Products

• 4610-69-9 (Z)-ethyl cinnamate 
• 4192-77-2 ethyl cinnamate 
• 61212-23-5 (Z)-ethyl 3-cyano-3-phenylacrylate 
• 6620-27-5 4,5-diphenylfuran-2(5H)-one 
• 78522-55-1 (Z)-4-oxo-3,4-diphenylbut-2-enoic acid ethyl ester 
• 583839-28-5 ethyl (Z)-3,5-diphenyl-2-penten-4-ynoate 
• 183614-26-8 ethyl (2E)-3-phenylhexa-2,5-dienoate 
• 911047-11-5 ethyl (2Z)-3-phenylnon-2-en-4-ynoate 
• 63382-85-4 (E)-5,5-dimethyl-2-phenylhex-2-en-4-one 
• 1002127-64-1 (Z)-3-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol 
• 1002127-66-3 (Z)-3-phenyl-3-(4-trifluoromethylphenyl)propenal 

Relevant academic research and scientific papers

Lead tetraacetate induced reaction of difluorodiiodomethane to alkenes and alkynes. Synthesis of fluorinated telechelic compounds

Lead tetraacetate (LTA) can smoothly induce the addition reaction of difluorodiiodomethane (1) with electron-rich alkenes at 60°in diglyme to give monoadducts (RCHICH2CF2I) and diadducts (RCHICH2)2CF2

Kinetic Resolution and Dynamic Kinetic Resolution of γ-Aryl-Substituted Butenolides via Copper-Catalyzed 1,4-Hydroboration

Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of γ-aryl and heteroaryl-substituted butenolides via CuH-catalyzed 1,4-hydroboration using pinacolborane is reported. With a copper-Ph-BPE catalyst, selectivity factors were extremely high (s=>400) with regard to the kinetic resolution of β-methyl-γ-phenyl butenolide; DKR was possible in the presence of an amine base (DBU), which facilitated racemization of the starting unsaturated lactones. The reaction provided easy access to highly enantioenriched γ-butyrolactones (>99% ee) containing β,γ-substituents. (Figure presented.).

Metal-Free Transfer Hydroiodination of C-C Multiple Bonds

The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.

BICYCLIC 1,3,4-OXADIAZOLE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTORS' MODULATORS

The present invention relates to bicyclic 1,3,4-oxadiazole derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

1,3,4-ALKENYL OXADIAZOLE AMINO ACID DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTORS' MODULATORS

The present invention relates to 1,3,4-alkenyl oxadiazole amino acid derivatives of formulae I and II, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

Discovery of novel 5,5-diarylpentadienamides as orally available transient receptor potential vanilloid 1 (TRPV1) antagonists

We have developed a novel and potent chemical series of 5,5-diphenylpentadienamides for targeting TRPV1 in vitro and in vivo. In this investigation, we examined a variety of replacements for the 5-position of dienamides with the goal of addressing issues related to pharmacokinetics. Our data suggest that substitution with alkoxy groups on the phenyl ring at the 5-position increases their ability to penetrate the blood-brain barrier. This investigation culminated in the discovery of compound (R)-36b, which showed a good pharmacokinetic profile. In vivo, compound (R)-36b was found to be effective at reversing mechanical allodynia in rats in a dose-dependent manner, and it reversed thermal hyperalgesia in a model of neuropathic pain induced by sciatic nerve injury.

Palladium-catalyzed alkoxycarbonylation of (Z)-2-en-4-yn carbonates leading to 2,3,5-trienoates

Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with

Stereoselective hydrohalogenation of alkynoic acids and their esters in ionic liquids

A novel procedure is described for the hydrohalogenation of alkynoic acids and their esters using N-alkylpyridinium ionic liquids. Hydrohalogenating agents were prepared by mixing N-alkylpyridinium halides with an equimolar amount of trifluoroacetic acid.

A convenient procedure for the efficient preparation of alkyl (Z)-3-iodo-2-alkenoates

Reaction of alkyl 2-alkynoates with sodium iodide (1.6-5.5 equiv.) in acetic acid (6.2-13 equiv.) at 115 deg C provides good to excellent yields of the corresponding alkyl (Z)-3-iodo-2-alkenoates.