29144-31-8

Basic information

• Product Name: (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde
• Synonyms: (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde;(1S)-3,4,5,6,7,8-Hexahydro-1α-[(4-methoxyphenyl)methyl]-2(1H)-isoquinolinecarbaldehyde;(1S)-1-[(4-methoxyphenyl)methyl]-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carbaldehyde
• CAS NO: 29144-31-8
• Molecular Formula: C₁₈H₂₃NO₂
• Molecular Weight: 285.38072
• EINECS: 249-471-6
• Product Categories: CMLLYL
• Mol File: 29144-31-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 466.8°Cat760mmHg
• Flash Point: 236.1°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 6.89E-09mmHg at 25°C
• Refractive Index: 1.577
• PKA: -0.81±0.40(Predicted)
• CAS DataBase Reference: (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde(29144-31-8)
• EPA Substance Registry System: (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde(29144-31-8)

Safety Data

• Hazardous Substances Data: 29144-31-8(Hazardous Substances Data)

Usage

Description

(S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde is a complex organic compound with a unique molecular structure. It is characterized by its hexahydro-isoquinoline core, which is substituted with a (4-methoxyphenyl)methyl group and a formyl group at the 2-position. (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde is of interest due to its potential applications in various fields, particularly in the synthesis of bioactive molecules and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
(S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde is used as an intermediate in the synthesis of various morphinans and isoquinoline alkaloids. These compounds are known for their diverse pharmacological properties, including analgesic, sedative, and anti-addictive effects. The unique structure of this compound allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
In the field of chemical research, (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde serves as a valuable building block for the creation of novel molecular structures. Its reactivity and functional groups make it an attractive candidate for further modification and exploration of its potential applications in various chemical and biological processes.
Used in Drug Synthesis:
(S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde is used as a key component in the synthesis of various pharmaceuticals, particularly those targeting the central nervous system. Its structural features enable the development of drugs with potential applications in the treatment of pain, addiction, and other neurological disorders. The synthesis of these drugs often involves the use of (S)-3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl](1H)-isoquinoline-2-carbaldehyde as a starting material or a crucial intermediate in the reaction sequence.

InChI:InChI=1/C18H23NO2/c1-21-16-8-6-14(7-9-16)12-18-17-5-3-2-4-15(17)10-11-19(18)13-20/h6-9,13,18H,2-5,10-12H2,1H3

Upstream product

• 116172-20-4 (Z)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 30356-07-1 (1S)-1-[(4-methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 109-94-4 formic acid ethyl ester 
• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 2721-62-2 1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 100466-48-6 ((S)-1-tert-Butoxymethyl-2-methyl-propyl)-[1-(3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-amine 
• 100466-49-7 ((S)-1-tert-Butoxymethyl-2-methyl-propyl)-[1-[(S)-1-(4-methoxy-benzyl)-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-amine 
• 100466-46-4 N-benzyl-5,6,7,8-tetrahydroisoquinolinium bromide 
• 100466-47-5 N-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 104-01-8 4-Methoxyphenylacetic acid 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 119-65-3 isoquinoline 
• 36556-06-6 5,6,7,8-tetrahydroisoquinoline 

Downstream Products

• 28973-48-0 (+)-3-methoxy-N-formylmorphinan 
• 89614-56-2 (S)-(+)-N-methyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 1531-12-0 norlevorphanol 
• 77-07-6 Levorphanol 
• 125-73-5 (+)-dextrorphan 
• 125-71-3 dextromethorphan 
• 1531-23-3 (+)-3-methoxymorphinan 
• 94006-07-2 (S)-(+)-N-formyl-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 

Relevant articles and documents

On the formation of a side product with hexahydroaporphine-like structure in the Grewe cyclization of dextromethorphan

Factors leading to the formation of a hexahydroaporphine-like cyclizing side product were studied systematically for the first time and the ratio of this side product was controlled effectively. To understand better the electronic effect of substrates on the formation of side products, different 1-benzyloctahydroisoquinolines with substituted groups on nitrogen or benzene ring were compared. A plausible mechanism of cyclizing reaction was proposed, and key intermediates as well as transition states were analyzed using DFT calculations.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF RESPIRATORY DISORDERS

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of respiratory disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of cough caused by minor throat and bronchial irritation (such as commonly accompanies the flu and common cold), as well as those resulting from inhaled particle irritants, upper respiratory infections, (pseudobulbar affect) in patients with amyotrophic lateral sclerosis and multiple sclerosis, neuropathic pain and pain associated with fibromyalgia.

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.