110901-90-1

Upstream product

• 6099-04-3 trans-3-methoxycinnamic acid 
• 96728-38-0 trans-[2-(3-methoxyphenyl)cyclopropane]carboxylic acid 
• 96728-45-9 (1S,2S)-2-(3-Methoxy-phenyl)-cyclopropanecarbonyl chloride 
• 591-31-1 3-methoxy-benzaldehyde 
• 766-85-8 3-methoxy-1-iodobenzene 
• 1759-53-1 cyclopropanecarboxylic acid 
• 38693-90-2 trans-3-(3-methoxyphenyl)acrylic acid methyl ester 
• 110826-32-9 (1R,2S)-N-<(R)-2-hydroxy-1-phenylethyl>-2-(3-methoxyphenyl)cyclopropanecarboxamide 
• 138298-59-6 ((1S,5S,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(1R,2R)-2-(3-methoxy-phenyl)-cyclopropyl]-methanone 
• 138298-52-9 (E)-1-((1S,5S,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(3-methoxy-phenyl)-propenone 
• 157604-00-7 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(3-methoxy-phenyl)-propenone 
• 15851-92-0 (E)-3-methoxycinnamoyl chloride 
• 157604-10-9 ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(1R,2R)-2-(3-methoxy-phenyl)-cyclopropyl]-methanone 

Downstream Products

• 110901-94-5 [(1R,2S)-2-(3-Methoxy-phenyl)-cyclopropyl]-dipropyl-amine 
• 110901-92-3 (1R,2S)-2-(3-Methoxy-phenyl)-cyclopropylamine 

Relevant academic research and scientific papers

PD(II)-CATALYZED ENANTIOSELECTIVE C-H ARYLATION OF FREE CARBOXYLIC ACIDS

The invention includes procedures for stereoselective β-arylation of carboxylic acids having a β-carbon atom. For example, stereoselective arylation procedures include the following reactions: (I)

Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Free Carboxylic Acids

A monoprotected aminoethyl amine chiral ligand based on an ethylenediamine backbone was developed to achieve Pd-catalyzed enantioselective C(sp3)-H arylation of cyclopropanecarboxylic and 2-aminoisobutyric acids without using exogenous directing groups. This new chiral catalyst affords new disconnection for preparing diverse chiral carboxylic acids from simple starting materials that are complementary to the various ring forming approaches.

Stereoselectivity and Generality of the Palladium-Catalysed Cyclopropanation of α,β-Unsaturated Carboxylic Acids Derivatized with Oppolzer's Sultam

A series of α,β-unsaturated carboxylic acids derivatized with camphorsultam 1 a s a chiral auxiliary has been stereoselectively cyclopropanated. the selectivity of the reaction produces cyclopropanated products with the 1R,2R absolute configuration as indicated by the optical rotations as well as by an X-ray structure determineation.The temperature dependence of the reaction was studied with three substrates. the highest stereoselectivity was obtained at temperatures above 25 deg C.Branching at the α- or β-carbons disfavours complete conversion, and electron-withdrawing substituents at these positions seem to prevent the reaction.The auxiliary was removed by using titanium(IV) isopropoxide in benzyl alcohol followed by alkaline hydrolysis of the intermediate ester. the potent 5-HT1A receptor agonist (1R,2S)-2-(2-hydroxyphenyl)-N,N-dipropylcyclopropylamine 13 was synthesized by this method

Stereoselective palladium-catalyzed cyclopropanation of α,β-unsaturated carboxylic acids derivatized with Oppolzer's sultam

N-enoyl sultans, derived from α,β-unsaturated carboxylic acids and bornane[10,2]sultam, undergo a stereoselective Pd-catalyzed cyclopropanation upon treatment with diazomethane. The stereoselectivity of the reaction is temperature dependent.

N,N-dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists

N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.