30277-63-5Relevant academic research and scientific papers
Nickel-Catalyzed Arylation of C(sp3)-O Bonds in Allylic Alkyl Ethers with Organoboron Compounds
Li, Xiaowei,Li, Yuxiu,Zhang, Zhong,Shi, Xiaolin,Liu, Ruihua,Wang, Zemin,Li, Xiangqian,Shi, Dayong
supporting information, p. 6612 - 6616 (2021/09/02)
A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds further prove the practicality of this synthetic method.
Absolute reactivity of arylallyl carbocations
Hallett-Tapley, Geniece,Cozens, Frances L.,Schepp, Norman P.
experimental part, p. 343 - 348 (2010/04/30)
A series of α-vinyl arylmethyl cations were generated and studied using nanosecond laser flash photolysis. Rate constants for the decay of the substituted α-vinyl arylmethyl cations were determined under solvolytic conditions in pure solvents and solvent
The photochemistry of ring-substituted cinnamyl acetates
Fleming,Renault,Grundy,Pincock
, p. 1146 - 1154 (2007/10/03)
The photochemistry of the (E)-cinnamyl acetates ((E)-1-aryl-3-propenyl acetates, 8a-8e) with substituents H, 4-CH3O, 3-CH3O, 4-CF3, and 3-CF3, respectively, was examined in both cyclohexane and methanol solvents. Alkene isomerization (E to Z) occurred more efficiently than other reactions and evidence is presented that this process occurs from the excited triplet state. In a slower process, 1,3-migration of the acetoxy group led to the rearranged 3-aryl-3-propenyl acetate isomers (9a-9e) as the major pathway, particularly in cylohexane. In methanol, the isomeric ethers 3-aryl-3-methoxypropene (14) and 1-aryl-3-methoxypropene (15) were formed by reaction of methanol with the photochemically generated cation. The combined yield of 14 and 15 (95% and 5%, respectively) was quantitative for the 4-methoxyphenyl compound (8b). Independent irradiations of the isomers 9a-9c demonstrated that the ethers 14 and 15 were primary photoproducts from 8 and not secondary photoproducts from 9. Fluorescence quantum yields and excited singlet state lifetimes indicated that the reactions, other than the E to Z isomerization, are from the excited singlet state.
Structure-activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages
Matsuda, Hisashi,Ando, Shin,Morikawa, Toshio,Kataoka, Shinya,Yoshikawa, Masayuki
, p. 1949 - 1953 (2007/10/03)
1′S-1′-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 μM. To clarify the structure-activity relationship of 1′S-1′- acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1′-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2′-3′ double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1′- and 2′-positions reduced the activity.
Electrochemical Methoxylation of Allyl and Propenyl Derivatives of Phenol and Phenol Ethers
Barba, Isidoro,Chinchilla, Rafael,Gomez, Cecilia
, p. 3270 - 3272 (2007/10/02)
Anodic oxidation of a methanolic solution of a number of phenols and phenol ethers (anethole, estragole, safrole, isosafrole, eugenol, and isoeugenol) in a single cell at constant current, with use of sodium methoxide or sodium methoxide-sodium perchlorate as the supporting electrolyte, afforded substitution and addition products, some of them not described previously in the literature.
