19966-45-1

Upstream product

• 111-81-9 Methyl 10-undecenoate 
• 17763-67-6 Phenyl triflate 
• 104828-34-4 B-(10-carbomethoxydecyl)-9-borabicyclo{3.3.1}nonane 
• 14811-73-5 10-oxo-decanoic acid methyl ester 
• 2834-05-1 11-bromoundecanoic acid 
• 929-33-9 methyl 11-iodoundecanoate 
• 591-51-5 phenyllithium 

Downstream Products

• 685887-85-8 methyl 11-[4-(4-methylbenzoyl)-phenyl]-undecanoate 
• 685887-87-0 11-[4-(4-methyl-benzoyl)-phenyl]-undecanoic acid anhydride 
• 128596-03-2 11-(4-(4-methylbenzoyl)phenyl)undecanoic acid 

Relevant academic research and scientific papers

Polymer-bound palladium-catalyzed cross-coupling of organoboron compounds with organic halides and organic triflates

The polymer-bound palladium-catalyzed cross-coupling reaction of electrophiles (i.e., halides and triflates) with oganoboron compounds to form carbon-carbon bonds was achieved at mild conditions with very high activity in the Suzuki coupling reaction. The polymeric catalyst can be easily separated from a reaction mixture and reused more than 10 times with no decrease in activity.

Synthesis of Benzophenone-Containing Analogues of Phosphatidylcholine

As part of a collaborative study of cellular efflux of cholesterol and phospholipids, photoactivable analogues 4-8 of phosphatidylcholine (PC) having benzophenone groups in the choline moiety and at the end of the C2 and C1 alkyl chains have been synthesized. The efficient preparation via Suzuki coupling of the appropriate long-chain benzophenone-containing carboxylic acid and alcohol and their incorporation by adaptation of known approaches into the acyl- and ether-linked PC analogues 6-8 are described. Development of a method for radiolabeling these PC analogues, via hydrogenation of a double bond in modified side chains, is also described.

Synthesis and nematocidal activity of aralkyl- and aralkenylamides related to piperamide on second-stage larvae of Toxocara canis

Seventy-nine aralkyl- and aralkenylamides related to piperamides were synthesized and their nematocidal activity against second-stage larvae of dog roundworm, Toxocara canis, was examined. The activity was greatly dependent on the alkyl chain length and the nature of the amine moiety, but was scarcely affected by the presence or absence of double bond(s) in the chain. The alkyl chain lengths which showed the strongest activity in a series of homologues were m=11 for the pyrrolidine amides and m=13 for the N- methylpiperazine amides. Although piperamides (3,4-methylenedioxyphenyl homologues) showed the strongest activity among the homologues tested, methoxy substituent(s) on the aromatic ring did not have much effect on the activity. However, conversion of the methoxy group to a hydroxy group greatly decreased the activity and shortened the chain length giving the strongest activity. Calculated log P values of non-phenolic aryl-piperamides fell in the range from 3.5 to 4.5, whereas those of hydroxyphenyl-piperamides were smaller, suggesting that different mechanisms are involved in the nematocidal activity of phenolic and non-phenolic compounds.

Palladium-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Organic Triflates

The cross-coupling reaction of 9-alkyl-9-borabicyclononane (9-R-9-BBN), 1-alkenyl-1,3,2-benzodioxaborole, or aryl boronic acid with 1-alkenyl or aryl triflates in the presence of K3PO4 (1.5 equiv) and a catalytic amount of Pd(PPh3)4 or Cl2Pd(dppf) resulted in high yields.The reaction conditions are sufficiently mild so that a variety of functionalized alkenes, alkadienes, and arenes are readily obtained.The utility of the present reaction was demonstrated by the cyclization of ω-alkenyl triflates leading to a benzo-fused cycloalkene and bicyclic alkene via a hydroboration intramolecular coupling sequence.