24734-71-2

Basic information

• Product Name: 5'-Methoxylaudanosine
• Synonyms: 5''-METHOXYLAUDANOSINE;1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]isoquinoline;6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 24734-71-2
• Molecular Formula: C₂₂H₂₉NO₅
• Molecular Weight: 387.47
• Product Categories: Aromatics;Heterocycles
• Mol File: 24734-71-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 492.6 °C at 760 mmHg
• Flash Point: 136.2 °C
• Appearance: Brown Oil
• Density: 1.121
• Solubility: Chloroform, Dichloromethane, Diethyl Ether, Methanol
• PKA: 7.73±0.40(Predicted)
• CAS DataBase Reference: 5'-Methoxylaudanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-Methoxylaudanosine(24734-71-2)
• EPA Substance Registry System: 5'-Methoxylaudanosine(24734-71-2)

Safety Data

• Hazardous Substances Data: 24734-71-2(Hazardous Substances Data)

Usage

Description

5'-Methoxylaudanosine is a naturally occurring alkaloid compound that serves as an intermediate in the synthesis of neuromuscular blocking agents. It is characterized by its brown oil chemical property.

Uses

Used in Pharmaceutical Industry:
5'-Methoxylaudanosine is used as an intermediate for the synthesis of neuromuscular blocking agents, which are essential in the development of medications that help induce muscle paralysis during surgical procedures or to aid in mechanical ventilation for patients with respiratory issues. Its role in the synthesis process is crucial for creating effective and safe pharmaceuticals in this application.

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 7668-87-3 N-β-(3,4-dimethoxyphenethyl)-3',4',5'-trimethoxyphenylacetamide 
• 50-00-0 formaldehyd 
• 61349-11-9 1-(3',4',5'-trimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 51714-24-0 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 110-88-3 1,3,5-Trioxan 
• 73554-57-1 6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 104832-01-1 (R)-N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium 2,3-dibenzoyl-L-tartarate 
• 99878-48-5 4-(3,4,5-trimethoxybenzyl)pyridine 

Relevant articles and documents

Synthesis method of 5'-methoxyl laudanosine

The invention discloses a synthesis method of 5'-methoxyl laudanthin, belonging to the technical field of organic synthesis. According to the method, 3,4-dimethoxyphenylethylamine and 3,4,5-trimethoxyphenylacetaldehyde are used as initial raw materials through an optimized process by utilizing the Pictet-Spengler reaction, dichloromethane is used as a solvent, and under the catalysis of a transition metal lewis acid catalyst, a dehydration reaction is performed through a dehydrating agent at 23-27 DEG C, or refluxing is performed in formic acid and phosphorus pentoxide is used for dehydration; and synthesized 6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinen reacts with a methyl donor by using formic acid as a solvent to obtain 5'-methoxy laudanosine. According to a technical scheme in the invention, a synthetic route is short in step, toxic and harmful reagents including phosphorus oxychloride and methylbenzene are not used, the steps of hydrogenation reduction and the like are avoided, total reaction yield is high, the obtained 5'-methoxy laudanin is high in purity, process cost is low, a process is environmentally friendly, process operation is simple, and the method has actual production value and can be used for industrial production.

Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis

A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.