130089-40-6

Usage

Natural occurrence

Found in plants such as tonka beans, sweet clover, and cassia cinnamon

Scent

Sweet

Usage

Perfumes and flavoring agent in food and beverages

Medicinal properties

Anticoagulant and potential anticancer agent

Safety concerns

Potential liver toxicity in high doses and banned as a food additive in some countries.

Upstream product

• 42710-40-7 3,4-Dihydro-1-phenyl-1H-2-benzopyran-3-ol 
• 130089-22-4 3-(2-Bromphenyl)-2-oxirancarbonsaeure 
• 100-52-7 benzaldehyde 
• 1232199-21-1 (2-ethynylphenyl)(phenyl)methanol 
• 38846-64-9 2-ethynylbenzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 130089-19-9 1-bromo-2-(2-methoxyethenyl)benzene 
• 130089-30-4 2-<2-(α-Hydroxybenzyl)-phenyl>-acetaldehydethylenacetal 
• 130089-27-9 2-<2-(α-Hydroxybenzyl)-phenyl>-acetaldehyddimethylacetal 
• 130089-21-3 Methyl-3-(2-bromphenyl)-2-oxirancarboxylat 
• 96557-36-7 2-(2-Bromphenyl)-acetaldehydethylenacetal 
• 112396-13-1 2-(2-bromophenyl)acetaldehyde dimethyl acetal 
• 96557-30-1 2-bromophenylacetaldehyde 

Relevant academic research and scientific papers

Efficient endo Cycloisomerization of Terminal Alkynols Catalyzed by a New Ruthenium Complex with 8-(Diphenylphosphino)quinoline Ligand and Mechanistic Investigation

Several new ruthenium complexes supported by the P,N-donor ligand 8-(diphenylphosphino)quinoline (DPPQ) were synthesized, including [RuCl2(DPPQ)2] (1), [Ru(μ-Cl)(DPPQ)2]2(BPh4)2 (2), and [RuCl(DPPQ)2Py](BF4) (3). Complex 2, with only 1 mol % loading, was found to be catalytically active for the endo cycloisomerization of various terminal alkynols to endo-cyclic enol ethers in moderate to excellent yields. In particular, the 7- and 8-endo heterocyclization can be achieved efficiently to give the seven-membered 3-benzoxepine and eight-membered 3-benzo[d]oxocine derivatives. The stoichiometric reactions of 2 with various alkynol substrates have been carried out to investigate the mechanism, which led to a series of seven-, six-, and five-membered oxacyclocarbene ruthenium complexes including [RuCl(DPPQ)2{=CCH2C6H4CH2CH2O}](BPh4) (12) and [RuCl(DPPQ)2{=CCH2(CH2)nCH2O}](BPh4) (n=3, 12′; n=2, 13; n=1, 14). The quantitative transformation of oxacyclocarbene 12 into catalyst 2 and 3-benzoxepine 5 a as well as the efficient catalytic activity of 12 for the endo-cyclization of 2-(2-ethynylphenyl)ethanol (4 a) demonstrated that 12 is a key intermediate involved in the catalytic cycle. Moreover, comparative studies on the modeling reactions and catalytic activity of the series of oxacyclocarbene complexes indicated that the different catalytic activity of 2 for the endo-cycloisomerization of different types of alkynols can be related to the reactivity of the respective ruthenium oxacyclocarbene intermediates.

Selective and efficient cycloisomerization of alkynols catalyzed by a new ruthenium complex with a tetradentate nitrogen-phosphorus mixed ligand

The new ruthenium complex [Ru(N3P)(OAc)][BPh4] (4), in which N3P is the N,P mixed tetradentate ligand N,N-bis[(pyridin-2-yl)methyl]-[2(diphenylphosphino)phenyl]methanamine was synthesized. The complex was found to be catalytically active for the endo cycloisomerization of alkynols. The catalytic reactions can be used to synthesize five-, six-, and seven-membered endo-cyclic enol ethers in good to excellent yields. A catalytic cycle involving a vinylidene intermediate was proposed for the catalytic reactions. Treatment of complex 4 with PhC≡CH and H2O gave the alkyl complex [Ru(CH2PhJ(CO)(N 3P)][BPh4] (30), which supports the assumption that the catalytic reactions involve addition of a hydroxyl group to the C=C bond of vinylidene ligands.