7116-39-4Relevant articles and documents
Method for synthesizing spiro compound of dihydro-1H-indene
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Paragraph 0031; 0032, (2018/09/20)
The invention provides a method for synthesizing a spiro compound 1 of dihydro-1H-indene. The method comprises the following steps: 1) reacting 3-methoxybenzaldehyde with carbethoxyethylidene triphenylphosphorane 2 in a halohydrocarbon solvent at room temperature to obtain a compound 3; 2) hydrogenating the compound 3 in an alcohol solvent in the presence of a catalyst to obtain a compound 4; 3) reacting the compound 4 with liquid bromine in a halohydrocarbon solvent to obtain a compound 5; 4) reacting the compound 5 with N-vinyl-2-pyrrolidone in an ether solvent in the presence of a strong alkali to obtain a compound 6; 5) refluxing the compound 6 in an aqueous diluted acid solution to perform a rearrangement reaction in order to obtain a compound 7; and 6) performing a cyclization reaction on the compound 7 in anhydrous toluene in the presence of butyl lithium at an appropriate temperature to obtain the compound 1. The method has the advantages of initiative synthesis route, ingenious design idea, easily available and cheap starting materials, mild synthesis process conditions in every step, easiness in industrial production, high yield of every step, and high overall yield of the product.
Structure activity relationship of brevenal hydrazide derivatives
Goodman, Allan,McCall, Jennifer R.,Jacocks, Henry M.,Thompson, Alysha,Baden, Daniel,Abraham, William M.,Bourdelais, Andrea
, p. 1839 - 1858 (2014/06/09)
Brevenal is a ladder frame polyether produced by the dinoflagellate Karenia brevis. This organism is also responsible for the production of the neurotoxic compounds known as brevetoxins. Ingestion or inhalation of the brevetoxins leads to adverse effects such as gastrointestinal maladies and bronchoconstriction. Brevenal shows antagonistic behavior to the brevetoxins and shows beneficial attributes when administered alone. For example, in an asthmatic sheep model, brevenal has been shown to increase tracheal mucosal velocity, an attribute which has led to its development as a potential treatment for Cystic Fibrosis. The mechanism of action of brevenal is poorly understood and the exact binding site has not been elucidated. In an attempt to further understand the mechanism of action of brevenal and potentially develop a second generation drug candidate, a series of brevenal derivatives were prepared through modification of the aldehyde moiety. These derivatives include aliphatic, aromatic and heteroaromatic hydrazide derivatives. The brevenal derivatives were tested using in vitro synaptosome binding assays to determine the ability of the compounds to displace brevetoxin and brevenal from their native receptors. A sheep inhalation model was used to determine if instillation of the brevenal derivatives resulted in bronchoconstriction. Only small modifications were tolerated, with larger moieties leading to loss of affinity for the brevenal receptor and bronchoconstriction in the sheep model.
Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps
Bonet, Amadeu,Gulyas, Henrik,Koshevoy, Igor O.,Estevan, Francisco,Sanau, Mercedes,Ubeda, M. Angeles,Fernandez, Elena
supporting information; experimental part, p. 6382 - 6390 (2010/08/03)
Diphenyl(3-methyl-2-indolyl)phosphine (C9H8NPPh 2, 1) gives stable dimeric palladium(II) complexes that contain the phosphine in P,Nbridging coordination mode. On treating 1 with [Pd(O 2CCH3)2], the new complexes [Pd(μ-C 9H7NPPh2)-(NCCH3)]2 (2) or [Pd(μ-C9H7NPPh2)-(μ-O 2CCH3)]2 (3) were isolated, depending on the solvent used, acetonitrile or toluene, respectively. Further reaction of 3 with the ammonium salt of 1 led to the substitution of one carboxylate ligand to afford [Pd(u-C9H7NPPh2)3(μ-O 2CCH3)] (4), in which the bimetallic unit is bonded by three C9H7NPPh2- moieties and one carboxylate group. Using this methodology, [Pd2(μ-C 6H4PPh2)2(μ-C9H 7NPPh2)(μ-O2CCX3)] (X = H (7); J. = F (8)) were synthesised from the ortho-metalated compounds [Pd(C 6H4PPh2)(μO2CCX3)], (X = H (5); J. = F (6)). Complexes 3, 4, 7, and 8 have been found to be active in the catalytic β-boration of α,β-unsaturated esters and ketones under mild reaction conditions. Hindrance of the carbonyl moiety has an influence on the reaction rate, but quantitative conversion was achieved in many cases. More remarkably, when aryl bromides were added to the reaction media, complex 7 induced a highly successful consecutive β-boration/crosscoupling reaction with dimethyl acrylamide as the substrate (99% conversion, 89 % isolated yield).
