14289-65-7

Usage

InChI:InChI=1/C11H14O/c1-2-9-12-10-8-11-6-4-3-5-7-11/h2-7H,1,8-10H2

Upstream product

• 106-95-6 allyl bromide 
• 103-45-7 acetic acid phenethyl ester 
• 501014-38-6 allyl 2-phenylethyl carbonate 
• 60-12-8 2-phenylethanol 
• 107-18-6 allyl alcohol 
• 22096-25-9 sodium phenethylate 

Downstream Products

• 60-12-8 2-phenylethanol 
• 124-11-8 non-1-ene 
• 154189-76-1 3-(2-phenylethoxy)-1-propanol 
• 94-47-3 2-Phenylethyl benzoate 
• 154189-58-9 2-[3-[2-Phenylethoxy]propylthio]acetic acid 
• 289896-28-2 2-(3-ethenylsulphonylpropoxy)ethylbenzene 
• 154189-61-4 4-hydroxy-7-{2-[(2-{[3-(2-phenylethoxy)propyl]sulfonyl}ethyl)amino]ethyl}-1,3-benzothiazol-2(3H)-one 
• 154189-60-3 2-[3-[2-Phenylethoxy]propylsulphonyl]acetic acid 

Relevant academic research and scientific papers

Dehydrative allylation of alcohols and deallylation of allyl ethers catalyzed by [CpRu(CH3CN)3]PF6 and 2-pyridinecarboxylie aeid derivatives. Effect of π-accepting ability and COOH acidity of ligand on reactivity

2-Quinolinecarboxylic acid efficiently promotes both the dehydrative allylation of alcohols and the deallylation of allyl ethers and esters in the presence of [CpRu(CH3CN)3JPF6. Comparison of the relative reactivity of various 4-substituted 2-pyridinecarboxylic acids has revealed two linear relations with different ρ values in the Hammett plots. These phenomena can be rationalized by the balance between the π-accepting ability of the pyridine moiety and the acidity of the carboxylic acid of the 2-pyridinecarboxylic acid derivative. Copyright

Nano-dispersed platinum(0) in organically modified silicate matrices as sustainable catalysts for a regioselective hydrosilylation of alkenes and alkynes

Nano-dispersed platinum(0) particles stabilized in a range of organically modified silicate (ORMOSIL) matrices are investigated as sustainable catalysts for the hydrosilylation of alkenes and alkynes. In this study, five different siloxane matrices including triethoxysilane (HTEOS), methyltriethoxysilane (MTES), ethyltriethoxysilane (ETES), triethoxyvinylsilane (TEVS) and propyltriethoxysilane (PTES) are investigated, and the distribution of the metal particles in these materials analyzed by transition electron microscopy (TEM). The particles appeared to be generally of a small size, with a diameter of ca. 2-5 nm in each of these catalysts, however the distribution is not equally uniform from one matrix to the other. HTEOS, MTES and ETES that respectively carry a hydrogen, a methyl and an ethyl group on the triethoxysilane moiety, displayed a more uniform distribution, while particles appeared to be more scattered in the remaining matrices. Catalysts with a uniform particles distribution produced higher and consistent yields, while those with poor particles distribution produced lower and almost random yields, suggesting that the uniformity in particle distribution, and by extension the nature of the siloxane matrix, are important for the catalytic properties of these materials. The scope of the reaction was broadened to a range of olefins, with a goal of investigating the tolerability of the reaction toward a number of reactive functional groups, resulting in the preparation of 28 compounds. This catalytic system also enabled the hydrosilylation of a limited number of alkynes under the optimized reaction conditions.

Hypervalent Iodine(III)-Mediated Oxidative Fluorination of Alkylsilanes by Fluoride Ions

The first example of a hypervalent iodine(III)-mediated oxidative fluorination of alkylsilanes by fluoride ions without the use of transition metals is demonstrated. This reaction is operationally simple, scalable, and proceeds under mild reaction conditions. Mechanistic studies suggest the involvement of a single-electron transfer resulting from the interaction of an organopentafluorosilicate and aryliodonium difluoride, which were generated in situ from the corresponding alkylsilane and iodosobenzene, respectively, in the presence of fluoride ions.

Step-economy etherification of acylated alcohols

An efficient and convenient protocol has been developed for ether bond formation in mild conditions. A mixture of primary/secondary ester and allylic/benzylic halide in tetrahydrofuran was treated with KOtBu at room temperature to give ether in high yield. This step economic method enabled direct alkylation of the acyl group masked O-nucleophiles. Application of this method in carbohydrate synthesis was feasible and chemo-selectivity can be achieved.

Highly reactive and chemoselective cleavage of allyl esters using an air- and moisture-stable [CpRu(IV)(π-C3H5)(2-quinolinecarboxylato)]PF6 catalyst

A new catalytic process for allyl ester cleavage has been developed by using a robust cationic CpRu(IV) π-allyl complex of 2-quinolinecarboxylic acid that can be stored for over six months in air without any loss of catalytic activity. The deprotection of various alcohols and acids can be attained simply with high reactivity and chemoselectivity under mild conditions. Furthermore, with continuous removal of the low-boiling point coproduct, a turnover number of 1 000 000 can be achieved.

[CpRu(IV)(π-C3H5)(2-quinolinecarboxylato)]PF 6 complex: A robust catalyst for the cleavage and formation of allyl ethers

A facile and efficient method for the quantitative synthesis of [CpRu(IV)(π-C3H5)(2-quinolinecarboxylato)]PF 6 from [CpRu(CH3CN)3]PF6, 2-quinolinecarboxylic acid, and 2-propen-1-ol has been established. The cationic Ru(IV) complex is air- and moisture-stable, and can be stored in a vial for at least six months. This complex realizes a simple and easy operation for both the deallylation of allyl ethers in methanol and the dehydrative allylation of alcohols. Furthermore, with removal of the volatile allyl methyl ether co-product from the reaction system, the robust catalyst can attain a turnover of 10000 cycles of allyl ether cleavage.

Method of removing allyl series protecting group using novel ruthenium complex and method of synthesizing allyl ethers

A cyclopentadienyl ruthenium (II) complex or (iv) complex having an α-imino acid type ligand or an α-amino acid type ligand.

Catalytic dehydrative allylation of alcohols

(Chemical Equation Presented) An environmentally benign synthesis of allyl ethers has been developed which can be applied to a highly chemoselective protection of hydroxyl groups. A highly efficient [CpRu]-2-quinolinecarboxylic acid (L) catalytic system was successfully employed for the dehydrative allylation of various alcohols without additional activators and solvent (see scheme; R = alkyl, aryl, multifunctional alkyl, Cp = C5H 5).

Development of a manufacturing process for sibenadet hydrochloride, the active ingredient of viozan

A process for commercial manufacture of the dual D2- β2 receptor agonist sibenadet hydrochloride has been developed. The process relies upon introduction of operationally simple chemistry at the final stages where two key intermediates are reacted to assemble the final molecule, isolated by crystallization. A nine-stage sequence for synthesis of the key amine hydrochloride intermediate was developed, and modifications to the original process are described. Major strategic improvements were made in definition of the final route to the "side chain" precursor molecule, the second key intermediate, hinging around a thiyl radical addition and subsequent high-yielding telescoped processes for synthesis of this highly crystalline benzoate ester. Development of these chemistries is discussed, together with some issues surrounding definition of the final validated commercial processes.

SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.

[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.