117422-50-1

Basic information

• Product Name: (3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine
• Synonyms: (3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine;(S)-5-methoxychroman-3-amine
• CAS NO: 117422-50-1
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Mol File: 117422-50-1.mol

Chemical Properties

• Boiling Point: 308.692°C at 760 mmHg
• Flash Point: 153.316°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.545
• PKA: 7.88±0.20(Predicted)
• CAS DataBase Reference: (3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine(117422-50-1)
• EPA Substance Registry System: (3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine(117422-50-1)

Safety Data

• Hazardous Substances Data: 117422-50-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine is used as a potential drug candidate for [application reason] due to its diverse pharmacological properties. Its unique molecular structure and stereochemistry may contribute to its potential therapeutic effects and interactions with biological targets.
Used in Medicinal Chemistry Research:
(3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine is used as a research compound for exploring its pharmacological properties and potential applications in drug development. Its benzopyran skeleton and amine group may offer opportunities for further chemical modifications and optimization to enhance its therapeutic potential.
Note: The specific application reason for the pharmaceutical industry and medicinal chemistry research is not provided in the materials. It can be filled in based on the actual research findings and potential therapeutic effects of the compound.

InChI:InChI=1/C10H13NO2/c1-12-9-3-2-4-10-8(9)5-7(11)6-13-10/h2-4,7H,5-6,11H2,1H3/t7-/m0/s1

Upstream product

• 110927-03-2 (R)-3-amino-5-methoxy-3,4dihydro-2H-1-benzopyran 
• 57234-28-3 1-methoxy-3-(methoxymethoxy)benzene 

Downstream Products

• 221359-96-2 C₂₄H₂₅NO₂ 
• 1072854-62-6 (3S)-N,N-dibenzyl-5-pyridin-3-ylchroman-3-amine 
• 1072854-56-8 (3S)-N,N-dibenzyl-5-pyridin-4-ylchroman-3-amine 
• 1072854-92-2 (3S)-N,N-dibenzyl-5-(5-fluoro-6-methoxypyridin-3-yl)chroman-3-amine 
• 1072854-88-6 {5-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]pyridin-2-yl}methanol 
• 1395896-82-8 (S)-(4-(3-(dibenzylamino)chroman-5-yl)pyridin-2-yl)methanol 
• 1395896-84-0 1-(5-((S)-3-(dibenzylamino)chroman-5-yl)pyridin-2-yl)ethanol 
• 1395896-86-2 (S)-(5-(3-(dibenzylamino)chroman-5-yl)-3-methylpyridin-2-yl)methanol 
• 1072855-02-7 (3S)-N,N-dibenzyl-5-pyrimidin-5-ylchroman-3-amine 
• 1072855-04-9 (3S)-N,N-dibenzyl-5-(2-methoxypyrimidin-5-yl)chroman-3-amine 
• 1072855-06-1 (3S)-N,N-dibenzyl-5-(2-methylpyrimidin-5-yl)chroman-3-amine 
• 1395896-87-3 (S)-N,N-dibenzyl-5-(5-methylpyrazin-2-yl)chroman-3-amine 
• 1072854-55-7 (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate 
• 221184-57-2 (3S)-3-(dibenzylamino)chroman-5-ol 

Relevant articles and documents

Synthesis of novel 5-substituted 3-amino-3,4-dihydro-2H-1-benzopyran derivatives and their interactions with the 5-HT(1A) receptor

A series of new enantiomerically pure 3-amino-3,4-dihydro-2H-1- benzopyrans (3-aminochromans) has been synthesized from (R)- and (S)-5- methoxy-3-amino-3,4-dihydro-2H-1-benzopyran. The absolute configuration of the respective (R)- and (S)-enantiomers was deduced from X-ray crystallography of (R)-3-(N-isopropylamino)-5-methoxy-3,4-dihydro-2H-1- benzopyran, (R)-9a. Various 5-substituents were introduced via palladium- catalyzed carbonylation of N-substituted 3-amino-5- trifluoromethanesulfonyloxy-3,4-dihydro-2H-1-benzopyran. The effect of N- and 5-substitution on affinity for the 5-HT(1A) receptor was evaluated in competition experiments using rat hippocampal membranes and [3H]8-OH-DPAT as radioligand. Selected compounds were also tested for their affinity to the D1 (rat striatum), D1 (rat striatum), D(2A) (human cloned), and 5-HT(2A) (rat cortex) receptors. The intrinsic activity of the compounds was evaluated by measuring their effect on VIP-stimulated cAMP production in GH4ZD10 cells stably transfected with the 5-HT(1A) receptor. High-affinity compounds with high selectivity for the 5-HT(1A) receptor were found among structures substituted with carboxylate esters, amides, and ketones in the 5-position. Primary and secondary amines bound with lower affinity than tertiary amines. Larger substituents were well-tolerated by the receptor, but the smaller N- ethyl-N-isopropyl bound with lower affinity. Generally, the (R)-enantiomers displayed higher affinity for the 5-HT(1A) receptor than the corresponding (S)-enantiomers. In the present series of compounds, both full and partial agonists were found.

Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2

Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affin

Synthesis of enantiomerically pure 3-aminochroman derivatives

Enantiomerically pure (3R)-amino-5-methoxy-3,4-dihydro-2H-1-benzopyran was successfully synthesised in nine steps starting from L-serine. The same synthetic pathway was used to prepare the (3S)-aminochroman derivative starting from D-serine. The enantiomeric purity of the final aminochroman derivatives was determined by capillary electrophoresis using β-cyclodextrin as the chiral selector.