869856-07-5

Basic information

• Product Name: (7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine
• Synonyms: (1S)-4,5-Dimethoxy-1-(aminomethyl)benzocyclobutane;(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine;Bicyclo[4.2.0]octa-1,3,5-triene-7-MethanaMine, 3,4-diMethoxy-, (7S)-;(1S)-4,5-Dimethoxy-1-(aminomethyl)benzocyclobutane HCl
• CAS NO: 869856-07-5
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.245
• EINECS: 104-523-4
• Mol File: 869856-07-5.mol

Chemical Properties

• Boiling Point: 308.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.113
• PKA: 9.70±0.29(Predicted)
• CAS DataBase Reference: (7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine(869856-07-5)
• EPA Substance Registry System: (7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine(869856-07-5)

Safety Data

• Hazardous Substances Data: 869856-07-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine is used as a building block in organic synthesis for the creation of more complex molecules. Its bicyclic ring system and amine functionality can be utilized in various chemical reactions to form a wide range of organic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine may serve as a starting material or intermediate for the development of new pharmaceutical agents. Its unique structure and functional groups can be modified to create potential drug candidates with specific biological activities.
Used in Pharmacology:
(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine may have potential applications in pharmacology, where it could be studied for its interactions with biological targets, such as enzymes, receptors, or ion channels. Further research and testing would be necessary to determine its specific properties, potential therapeutic effects, and safety profile.
Used in Drug Design and Development:
In the pharmaceutical industry, (7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-methanamine can be used as a template for drug design and development. Its unique structural features and functional groups can be optimized to enhance the compound's pharmacokinetic and pharmacodynamic properties, leading to the discovery of new therapeutic agents.

Upstream product

• 3459-92-5 DBC 
• 73344-75-9 (±)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine 

Relevant articles and documents

Exploiting the Biocatalytic Toolbox for the Asymmetric Synthesis of the Heart-Rate Reducing Agent Ivabradine

Several chemoenzymatic routes have been evaluated for the production of the heart-rate reducing agent ivabradine. Lipases and ω-transaminases have been identified as useful biocatalysts for the preparation of key enantiopure precursors. The lipase-catalysed kinetic resolution by alkoxycarbonylation of a racemic primary amine and subsequent chemical reduction of the resulting carbamate provided an N-methylated (S)-amine, one step away from ivabradine. Alternatively, the dynamic kinetic resolution by asymmetric bioamination of an aldehyde precursor enabled, in a four-step sequence, the preparative scale synthesis of enantiopure ivabradine in 50% overall yield. (Figure presented.).

PROCESS FOR THE ENZYMATIC SYNTHESIS OF (7S)-1-(3,4-DIMETHOXYBICYCLO[4.2.0]OCTA-1,3,5-TRIEN-7-YL) N-METHYL METHANAMINE, AND APPLICATION IN THE SYNTHESIS OF IVABRADINE AND SALTS THEREOF

Synthesizing carbamate (IX) comprises performing an enantioselective enzymatic acylation of racemic form of (3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)methanamine (IV) with a lipase (EC 3.1.1.3 in the international classification of enzymes) by carbonate with 1-15 molar equivalents in organic solvents, aqueous solvents, a mixture of organic solvents and/or mixture of organic and aqueous solvents at a concentration of 5-500 g/l per liter of solvents and their mixtures, a E/S ratio of 10/1 to 1/100 and a temperature of 25-40[deg] C. Synthesizing carbamate of formula (IX) comprises performing an enantioselective enzymatic acylation of racemic form of (3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)methanamine of formula (IV) with a lipase (EC 3.1.1.3 in the international classification of enzymes) by carbonate of formula (R1O-(CO)-OR1) with 1-15 molar equivalents in organic solvents, aqueous solvents, a mixture of organic solvents and/or mixture of organic and aqueous solvents at a concentration of 5-500 g/l per liter of solvents and their mixtures, a E/S ratio of 10/1 to 1/100 and a temperature of 25-40[deg] C. R1 : linear or branched 1-6C-alkyl, allyl or benzyl. An independent claim is included for synthesis of (7S)-1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-yl) N-methyl methanamine of formula (I) comprising performing enzymatic acylation of (IV) to obtain (IX), and performing reduction step using a reducing agent consisting of lithium tetrahydridoaluminate and sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) to obtain (I). ACTIVITY : Cardiant; Vasotropic; Antianginal; Antiarrhythmic. MECHANISM OF ACTION : None given.