79465-07-9

Upstream product

• 447-53-0 1,2-Dihydronaphthalene 
• 119-64-2 tetralin 
• 75238-77-6 1-Bromo-1,2,3,4-tetrahydronaphthalene 
• 2018-87-3 (+/-)-trans-1,2-dibromo-1,2,3,4-tetrahydronaphthalene 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 91-20-3 naphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 2018-87-3 1,2-dibromo-1,2,3,4-tetrahydro-naphthalene 

Downstream Products

• 127531-61-7 trans-1-(2-hydroxyethylcyclohexylamino)-1,2,3,4-tetrahydro-2-naphthol 
• 86800-08-0 trans-N-Benzyl-α-amino-β-tetralol 
• 17180-88-0 (1R,2S)-(+)-naphthalene 1,2-oxide 
• 122874-29-7 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2,4-dibromo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 
• 122874-29-7 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-2,4-dibromo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 
• 122874-29-7 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-2,4-dibromo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 
• 109470-12-4 trans-1-Benzoylamino-2-hydroxy-tetralin 
• 112108-01-7 ecopipam 
• 91-59-8 naphthalen-2-ylamine 
• 32338-05-9 2-(phenylsulfonyl)naphthalene 
• 7570-96-9 2-naphthyl phenyl sulfide 

Relevant academic research and scientific papers

Development of an efficient process for the preparation of Sch 39166: Aziridinium chemistry on scale

A large-scale synthesis of a tricyclic D1/D5 dopamine antagonist based on regio- and stereoselective ring opening of an aziridinium ion with a Grignard reagent was optimized and scaled up.

Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides

A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.

Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.

Bromination of olefins with HBr and DMSO

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

From simple organobromides or olefins to highly value-added bromohydrins: A versatile performance of dimethyl sulfoxide

A novel and efficient direct transformation of secondary bromides or olefins to highly value-added bromohydrins has been disclosed. Dimethyl sulfoxide (DMSO), a cheap and common solvent, performs its versatile role as a solvent, an essential oxidant, and also as an oxygen source in this bromohydrin synthesis.

Discovery of a novel class of dimeric smac mimetics as potent IAP antagonists resulting in a clinical candidate for the treatment of cancer (AZD5582)

A series of dimeric compounds based on the AVPI motif of Smac were designed and prepared as antagonists of the inhibitor of apoptosis proteins (IAPs). Optimization of cellular potency, physical properties, and pharmacokinetic parameters led to the identification of compound 14 (AZD5582), which binds potently to the BIR3 domains of cIAP1, cIAP2, and XIAP (IC50 = 15, 21, and 15 nM, respectively). This compound causes cIAP1 degradation and induces apoptosis in the MDA-MB-231 breast cancer cell line at subnanomolar concentrations in vitro. When administered intravenously to MDA-MB-231 xenograft-bearing mice, 14 results in cIAP1 degradation and caspase-3 cleavage within tumor cells and causes substantial tumor regressions following two weekly doses of 3.0 mg/kg. Antiproliferative effects are observed with 14 in only a small subset of the over 200 cancer cell lines examined, consistent with other published IAP inhibitors. As a result of its in vitro and in vivo profile, 14 was nominated as a candidate for clinical development.

Highly regio- and diastereoselective halohydroxylation of olefins: A facile synthesis of vicinal halohydrins

An efficient method for the synthesis of vicinal chlorohydrin or bromohydrin derivatives has been developed on the basis of direct halohydroxylation of various olefins with electrondonating or withdrawing substituent. The reactions were carried out under mild conditions in the presence of N-tosyl-l-threonine (NTsLT) as an acidic additive using chloramine T trihydrate, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) or N-bromoacetamide (AcNHBr) as the halogen source, respectively, affording the corresponding vicinal halohydrins in good to high yields with excellent regio- and stereoselectivities.

Asymmetric synthesis of chiral 1,3-diaminopropanols: Bisoxazolidine- catalyzed C-C bond formation with α-keto amides

Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF 3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.

Organocatalysis in the stereoselective bromohydrin reaction of alkenes

An efficient regio- and stereo-selective (>99:1) trans-bromohydrination (bromohydroxylation and bromomethoxylation) of alkenes including α,β-unsaturated carbonyl compounds with N-bromosuccinimide (NBS) has been achieved by using 1.0 mol% of N,N'-diarylthi

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.