14864-24-5Relevant academic research and scientific papers
Endo-selective pd-catalyzed silyl methyl heck reaction
Parasram, Marvin,Iaroshenko, Viktor O.,Gevorgyan, Vladimir
supporting information, p. 17926 - 17929 (2015/03/04)
A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.
A novel and efficient procedure for the preparation of allylic alcohols from α,β-unsaturated carboxylic esters using LiAlH4/BnCl
Wang, Xiaolong,Li, Xiaodong,Xue, Jijun,Zhao, Yuling,Zhang, Yumei
experimental part, p. 413 - 415 (2009/05/11)
A new and efficient method for the reduction of α,β-unsaturated carboxylic esters to allylic alcohols utilizing LiAlH4/BnCl is described. Various α,β-unsaturated esters, including the coumarins bearing α,β-unsaturated lactone skeleton, can be converted smoothly into their corresponding allylic alcohols in high yields under mild conditions with short reaction times.
Design, synthesis, and bioavailability evaluation of coumarin-based prodrug of meptazinol
Xie, Qiong,Wang, Xiaolin,Wang, Xinghai,Jiang, Zhiqiang,Qiu, Zhuibai
, p. 4953 - 4956 (2007/10/03)
Based on the known coumarin-based prodrug system, a new meptazinol (Z)-3-[2-(propionyloxy) phenyl]-2-propenoic ester (3) was designed and synthesized as prodrug to minimize the first-pass effect of meptazinol (1) and improve the oral bioavailability. The
Coumarin-based prodrugs. Part 3: Structural effects on the release kinetics of esterase-sensitive prodrugs of amines
Wang, Binghe,Zhang, Huijuan,Zheng, Ailian,Wang, Wei
, p. 417 - 426 (2007/10/03)
To study the structural effects on the release kinetics of a coumarin- based esterase-sensitive prodrug system, two series of compounds with varying structural features of the ester 'trigger' part and the amine 'drug' part were synthesized. The half-lives of the nine model prodrugs in the presence of porcine liver esterase ranged from about 2 min to 190 min. The steric bulkiness of the acyl group seems to have only a very minor effect on the half-lives of the esterase-triggered release of amines from the model prodrugs. The rate of the lactonization depends on the steric and electronic properties of the amine moiety.
Chemical feasibility studies of a potential coumarin-based prodrug system
Wang, Binghe,Zhang, Huijuan,Wang, Wei
, p. 945 - 950 (2007/10/03)
By using model amines, several amides of coumarinic acid with the phenolic hydroxyl group protected as an ester were prepared. These model amides underwent a facile (t( 1/2 ) 1.5-31 min) lactonization to release the original amine compounds upon esterase catalyzed hydrolysis of the phenolic ester. Such a system can be used for the preparation of esterase-sensitive prodrugs of amine-containing compounds or peptids.
Selectivity in sodium borohydride reduction of coumarin encapsulated in β-cyclodextrin
Pitchumani, Kasi,Velusamy, Ponnusamy,Srinivasan, Chockalingam
, p. 12979 - 12988 (2007/10/02)
The sodium borohydride reduction of coumarin to the corresponding alkanol and alkenol has been investigated in the presence and absence of β-cyclodextrin (β-CD). Excellent selectivity is observed when β-CD-coumarin complex is reduced in solid state at 0°C and the alkenol, cis-o-hydroxycinnamyl alcohol is the major product. Complex formation and the mode of substrate insertion into the CD cavity have been analysed using various physical methods.
