51773-23-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly morphinans and isoquinoline alkaloids. Its unique structure allows for the creation of a wide range of bioactive molecules with potential therapeutic applications.
Used in Chemical Research:
(+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde is also used as a research tool in the field of organic chemistry, where it can be employed to study the reactivity and properties of various functional groups and structural motifs. Its use in chemical research can lead to the development of new synthetic methods and the discovery of novel compounds with potential applications in various industries.
Used in Drug Delivery Systems:
Similar to gallotannin, (+)-3,4,5,6,7,8-hexahydro-1-(p-Methoxybenzyl)-2(1H)-Isoquinolinecarboxaldehyde could potentially be used in the development of drug delivery systems. These systems could be designed to improve the bioavailability and therapeutic efficacy of the compound, as well as to enhance its delivery to specific target sites within the body.

Upstream product

• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 116172-20-4 (Z)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline 

Relevant academic research and scientific papers

General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

In the presence of a small amount of RuX2[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4- tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100%) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used for synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.

New efficient methods for the synthesis and in-situ preparation of ruthenium(II) complexes of atropisomeric diphosphines and their application in asymmetric catalytic hydrogenations

A new synthetically useful method for the synthesis of the diphosphine ruthenium dicarboxylato complexes (P-P)Ru(O2CR)2(R= CF3 and CH3) is presented, which uses the easily accessible complex (COD)2Ru2(μ-O2CCF3)4 as starting material. This complex as well as (COD)(Ru(ηO2CCH3)2 and (COD)2Ru2Cl4(NCCH3) have been shown to be suitable precursor complexes for the in-situ preparation of ruthenium(II) dicarboxylato and dichloro complexes of atropisomeric diphosphines, respectively. The high efficacy of the preformed and in-situ generated ruthenium complexes as precatalysts is demonstrated in asymmetric hydrogenations of allylic alcohols, enamides, and a β-keto ester.