130089-19-9

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 20763-19-3 (methoxymethylene)triphenylphosphorane 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 

Downstream Products

• 172794-65-9 (4R,5R)-(-)-2-(2-bromobenzyl)-4,5-dimethyl-1,3-dioxolane 
• 172794-68-2 (4R,5R)-2-(2-Bromo-benzyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 96557-30-1 2-bromophenylacetaldehyde 
• 1257244-35-1 2-(2-methoxyvinyl)benzaldehyde 
• 1379674-99-3 C₁₃H₁₇ClSi 
• 1379674-62-0 1-(2-chloroethyl)-2-ethynylbenzene 
• 1074-16-4 2-bromophenylethyl alcohol 
• 75534-18-8 1-bromo-2-(2-chloro-ethyl)benzene 
• 1416799-62-6 1-(2-bromophenyl)-4-(2-phenoxyphenyl)but-3-yn-2-ol 
• 3377-71-7 N-benzylindole 
• 85-01-8 phenanthrene 
• 2531-84-2 2-methylphenathrene 
• 832-64-4 4-methylphenanthrene 
• 523-41-1 2-Fluor-phenanthren 

Relevant academic research and scientific papers

Preparation method of aporphine alkaloid

The invention discloses a preparation method of aporphine alkaloid as shown in a formula III. The method comprises the following steps: taking a benzaldehyde compound as shown in a formula III-0 as a raw material, and sequentially carrying out Wittig reaction, Pictet-Spengler reaction, Heck reaction and palladium carbon hydrogen deprotection. A bromine-containing benzaldehyde derivative is selected as a raw material, the carbon-carbon coupling co-production rate and the reaction rate are increased through bromine atoms, and the reaction activity is improved; benzyl chloroformate is adopted for NH protection, and an electron withdrawing group is introduced, so that the reaction yield can be improved; and a styrene methyl ether derivative directly reacts with an acylated phenylethylamine derivative in an acid catalysis system by adopting a one-pot method so as to obtain benzyl tetrahydroisoquinoline. The preparation method has the advantages of mild reaction conditions, low toxicity of used reagents, easily available raw materials, convenient post-treatment and simpler reaction route compared with previous reports, and can be suitable for various reaction substrates.

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-ric

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature

Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

Synthesis and Structure-Affinity Relationships of Spirocyclic Benzopyrans with Exocyclic Amino Moiety

σ1 and/or σ2 receptors play a crucial role in pathological conditions such as pain, neurodegenerative disorders, and cancer. A set of spirocyclic cyclohexanes with diverse O-heterocycles and amino moieties (general structure III) was prepared and pharmacologically evaluated. In structure-activity relationships studies, the σ1 receptor affinity and σ1:σ2 selectivity were correlated with the stereochemistry, the kind and substitution pattern of the O-heterocycle, and the substituents at the exocyclic amino moiety. cis-configured 2-benzopyran cis-11b bearing a methoxy group and a tertiary cyclohexylmethylamino moiety showed the highest σ1 affinity (Ki = 1.9 nM) of this series of compounds. In a Ca2+ influx assay, cis-11b behaved as a σ1 antagonist. cis-11b reveals high selectivity over σ2 and opioid receptors. The interactions of the novel σ1 ligands were analyzed on the molecular level using the recently reported X-ray crystal structure of the σ1 receptor protein. The protonated amino moiety forms a persistent salt bridge with E172. The spiro[benzopyran-1,1′-cyclohexane] scaffold and the cyclohexylmethyl moiety occupy two hydrophobic pockets. Exchange of the N-cyclohexylmethyl moiety by a benzyl group led unexpectedly to potent and selective μ-opioid receptor ligands.

Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors

Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biologically active molecules containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing an array of substituents (methyl, isopropyl, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (Ki 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogues that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biology.

CuCN-mediated cascade cyclization of 4-(2-bromophenyl)-2-butenoates: A high-yield synthesis of substituted naphthalene amino esters

A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2- butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish

Indoles synthesized from amines via copper catalysis

N-Substituted indoles are synthesized from primary amines through a tandem reaction sequence. Initial condensation of the amine with an α-(o-haloaryl)ketone or aldehyde is followed by intramolecular aryl amination catalyzed by CuI. A variety of anilines and alkyl amines, including those with significant steric demands, are converted to indoles in high yields and with varying indole substitution.

Palladium-catalyzed domino carbopalladation/C-H activation for the synthesis of tetrasubstituted alkenes bearing five- and seven-membered rings

A Pd-catalyzed domino carbopalladation/C-H-activation reaction of phenoxyphenyl-substituted propargylic alcohols was used for the synthesis of tetrasubstituted alkenes bearing either a dihydroindene or benzo[7]annulene motif. These compounds are of intere

Palladium-catalyzed domino carbopalladation/C-H activation for the synthesis of tetrasubstituted alkenes bearing five- and seven-membered rings

A Pd-catalyzed domino carbopalladation/C-H-activation reaction of phenoxyphenyl-substituted propargylic alcohols was used for the synthesis of tetrasubstituted alkenes bearing either a dihydroindene or benzo[7]annulene motif. These compounds are of intere