62222-44-0Relevant academic research and scientific papers
Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi
Chen, Dong-Dong,Zhang, Bing-Yu,Liu, Xiu-Xiu,Li, Xing-Qiang,Yang, Xin-Juan,Zhou, Le
supporting information, p. 1149 - 1153 (2018/03/05)
A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.
Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
Naik, Mayuri M.,Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
, p. 5221 - 5233 (2014/07/08)
Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation- esterification process at 120-130°C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2- ones were obtained in 5-85% yields.
Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
Naik, Mayuri M.,Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
, p. 5221 - 5233 (2014/12/10)
Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 °C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields.
Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine
Kamat, Durga P.,Tilve, Santosh G.,Kamat, Vijayendra P.
experimental part, p. 4469 - 4472 (2012/09/22)
Molecular iodine was used as a catalyst in the [3+3] cyclocoupling of phenols and cinnamic acids which proceeds via a tandem esterification- hydroarylation process at 120-130 °C under solvent-free conditions. Substituted 4-aryl-3,4-dihydrobenzopyran-2-one
Selective synthesis of 3,4-dihydrocoumarins and chalcones from substituted aryl cinnamic esters
Jeon, Jae-Ho,Yang, Deok-Mo,Jun, Jong-Gab
experimental part, p. 65 - 70 (2011/10/31)
Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.
Social self-sorting: Alternating supramolecular oligomer consisting of isomers
Tomimasu, Naoki,Kanaya, Akira,Takashima, Yoshinori,Yamaguchi, Hiroyasu,Harada, Akira
supporting information; experimental part, p. 12339 - 12343 (2010/01/30)
The isomers of cinnamoyl α-CDs (2-CiO-α-CD and 3-CiO-α-CD) organize by themselves to give different types of supramolecular complexes in aqueous solutions. 2-CiO-α-CD was found to form a double-threaded dimer, which was characterized by single crystal X-r
Switching of polymerization activity of cinnamoyl-α-cyclodextrin
Osaki, Motofumi,Takashima, Yoshinori,Yamaguchi, Hiroyasu,Harada, Akira
experimental part, p. 1646 - 1651 (2009/06/28)
Cinnamoyl α-cyclodextrin (α-CD) has been found to initiate polymerization of δ-valerolactone (δ-VL) to give a polymer in high yield. By the presence of the cinnamoyl group, hydrogen bond was formed between the carbonyl oxygen of δ-VL and the hydroxyl grou
Participation of an Extended p-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl 4-Hydroxycinnamates
Cevasco, Giorgio,Thea, Sergio
, p. 6274 - 6278 (2007/10/02)
The alkaline hydrolysis of 4-hydroxycinnamate esters of acidic phenols follows an E1cB mechanism and involves the participation of an "extended" p-oxo ketene intermediate.The apparent bimolecular rate constant (kaKa/Kw) for the hydrolysis of the 2,4-dinitrophenyl ester is some 2500-fold larger than that determined from the Hammett relationship for the BAc2 alkaline hydrolysis of substituted 2,4-dinitrophenyl cinnamates.The positive value of entropy of activation for the hydrolysis of 2,4-dinitrophenyl 4'-hydroxycinnamate and trapping experiments with nitrogen nucleophiles are consistent with the dissociative pathway.A change from a E1cB to a BAc2 mechanism is expected for esters with leaving groups having pKa higher than ca. 6.7.The higher E1cB reactivity of 2,4-dinitrophenyl 4'-hydroxycinnamate compared to that of the corresponding 4'-hydroxybenzoate is due to the vinylene group that further favors the dissociative route, probably increasing the stability of the unsaturated intermediate.
Structure-Reactivity Relationships in Nucleophilic Reactions on Cinnamoyl Azide and Phenyl Cinnamates. Kinetic Stability of the Acyl Azide and Relative Leaving Ability of Nitrogen and Oxygen
Suh, Junghun,Lee, Byung Hyun
, p. 3103 - 3107 (2007/10/02)
The alkaline hydrolysis and aminolysis of cinnamoyl azide and aryl-substituted phenyl cinnamates and the azidolysis of the phenyl cinnamates have been studied.The positions of the rate-determining steps in the reactions are identified by the structure-reactivity relationships.The enhanced affinity of azide ion for an acyl carbon compared with its basicity is proposed to account for the observed kinetic stability of cinnamoyl azide toward alkaline hydrolysis and aminolysis.Azide ion resists expulsion from the tetrahedral intermediate more than quinuclidine derivatives but less than phenolates.This is explained in terms of the electron withdrawal as well as electron donation by resonance.
