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
• Article Data: 3

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

General Description

"(3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine" is a chemical compound that belongs to the class of benzopyran amines. It is a derivative of 2H-1-benzopyran, which is a type of organic compound with a benzopyran skeleton. This particular compound has a 5-methoxy substituent on the benzene ring and an amine group at the third carbon position. The molecular structure contains a 3S stereochemistry, indicating the configuration of the chiral center at the third carbon. (3S)-3,4-dihydro-5-methoxy-2H-1-Benzopyran-3-amine may have diverse pharmacological properties and could potentially be used in medicinal chemistry for drug development or research purposes.

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

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

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.

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.