144493-15-2

Upstream product

• 629-05-0 n-octyne 
• 619-44-3 methyl 4-iodobenzoate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-58-9 4-iodobenzoic acid 
• 68113-72-4 1-octynylzinc chloride 
• 1126-46-1 Methyl 4-chlorobenzoate 

Downstream Products

• 3575-31-3 4-octylbenzoic acid 
• 50606-97-8 p-n-octylbenzoyl chloride 
• 54256-51-8 4-octyl-benzoic acid methyl ester 
• 144492-91-1 Methyl (E)-4-(2-hexyl-3-hydroxy-5-phenyl-1-pentenyl)benzoate 
• 144493-06-1 Methyl (E)-4-(1-heptylidene-2-hydroxy-4-phenylbutyl)benzoate 

Relevant academic research and scientific papers

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida

A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.

Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: Use of surfactants in cross-coupling reactions

Aqueous Sonogashira coupling between lipophilic terminal alkynes and aryl bromides or iodides gave moderate to high yields at 40°C using readily available and inexpensive surfactants (2.0 w/v% in water) such as SDS and CTAB. The catalyst precursor was 2 m

A Palladium Bipyridyl Complex Grafted onto Nanosized MCM-41 as a Heterogeneous Catalyst for Negishi Coupling

The Negishi coupling of aryl bromides or acyl chlorides with organozinc chlorides catalyzed by a palladium bipyridyl complex anchored on nanosized mobile crystalline material 41 (MCM-41) were investigated. The reactions proceeded smoothly with a very low catalyst loading in THF at 70°C for electron-deficient aryl bromides, which gave good to high yields of the Negishi coupling products. However, reactions in toluene at 110°C were required if electron-rich aryl bromides were employed. For acyl chlorides, the reactions could be performed in THF at 50°C and the corresponding ketones and ynones were obtained in high yields. After centrifugation, it was possible to easily recover the supported catalyst from the reaction mixture, and this could be reused several times without any retreatment or regeneration with only a slight decrease in activity.

Synthesis and biological evaluation of sphingosine kinase substrates as sphingosine-1-phosphate receptor prodrugs

In the search for bioactive sphingosine 1-phosphate (S1P) receptor ligands, a series of 2-amino-2-heterocyclic-propanols were synthesized. These molecules were discovered to be substrates of human-sphingosine kinases 1 and 2 (SPHK1 and SPHK2). When phosphorylated, the resultant phosphates showed varied activities at the five sphingosine-1-phosphate (S1P) receptors (S1P1-5). Agonism at S1P1 was displayed in vivo by induction of lymphopenia. A stereochemical preference of the quaternary carbon was crucial for phosphorylation by the kinases and alters binding affinities at the S1P receptors. Oxazole and oxadiazole compounds are superior kinase substrates to FTY720, the prototypical prodrug immunomodulator, fingolimod (FTY720). The oxazole-derived structure was the most active for human SPHK2. Imidazole analogues were less active substrates for SPHKs, but more potent and selective agonists of the S1P1 receptor; additionally, the imidazole class of compounds rendered mice lymphopenic.

Improved palladium-catalyzed sonogashira coupling reactions of aryl chlorides

The improved palladium-catalyzed Sonogashira coupling reactions of aryl chlorides without the necessity to add copper salts were analyzed for the development of palladacycles, adamantylphosphines, carhene ligands, and 2-phosphino-N-arylin-doles and -pyrro

Copper-catalyzed Sonogashira-type reactions under mild palladium-free conditions

(Chemical Equation Presented) We have developed an inexpensive catalytic system using a readily available copper/ligand combination for the Sonogashira-type cross-coupling of aryl iodides and phenyl- and hexyl-acetylene which affords disubstituted alkynes