5701-00-8

Basic information

• Product Name: Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-((4-methoxyphenyl)methyl)-2-methyl-, (R)-
• CAS NO: 5701-00-8
• Molecular Weight: 327.423
• Mol File: 5701-00-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-((4-methoxyphenyl)methyl)-2-methyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-((4-methoxyphenyl)methyl)-2-methyl-, (R)-(5701-00-8)
• EPA Substance Registry System: Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-((4-methoxyphenyl)methyl)-2-methyl-, (R)-(5701-00-8)

Safety Data

• Hazardous Substances Data: 5701-00-8(Hazardous Substances Data)

Upstream product

• 477-57-6 (+)-isotetrandrine 
• 186581-53-3 diazomethane 
• 477-57-6 pheanthine 
• 524-20-9 armepavine 
• 1246431-52-6 C₁₉H₁₇Cl₃O₇ 
• 1580442-46-1 C₅₃H₅₈N₂O₈ 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 228271-22-5 6,7-dimethoxy-1-[[4-[5-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinyl)methyl-2-methoxy]phenoxy]benzyl]-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 409366-27-4 (3,5-dichloro-4-hydroxyphenyl)acetic acid methyl ester 
• 42583-41-5 2-{4-[5-(carboxymethyl)-2-methoxyphenoxy]phenyl}acetic acid 
• 1580442-44-9 methyl 2-{4-hydroxy-3-[4-(2-methoxy-2-oxoethyl)phenoxy]phenyl}acetate 
• 1246431-54-8 C₁₈H₁₅Cl₃O₆ 
• 321669-88-9 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 
• 321670-11-5 (1R)-N-(8-menthyl)-1-(p-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 7630-50-4 N,O-dimethyl-N-norarmepavine methyliodide 

Relevant articles and documents

Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.

Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro

Forty-one isoquinoline alkaloids were tested for antiplatelet aggregation effects. Among them, (-)-discretamine (6), protopine (7), ochotensimine (18), O-methylarmepavinemethine (23), lindoldhamine (25), isotetrandrine (26), thalicarpine (27), papaverine (28), and D-(+)-N-norarmepavine (32) exhibited significant inhibitory activity towards adenosine 5′-diphosphate (ADP)-, arachidonic acid (AA)-, collagen-, and/or platelet-activating factor (PAF)-induced platelet aggregation. The results are discussed on the basis of structure-activity relationships. Georg Thieme Verlag KG Stuttgart.

Dehatrine, an antimalarial bisbenzylisoquinoline alkaloid from the Indonesian medicinal plant Beilschmiedia madang, isolated as a mixture of two rotational isomers

Through bioassay-guided separations of the chemical constituents of the Indonesian medicinal plant Beilschmiedia madang BL. A bisbenzylisoquinoline alkaloid was obtained as the major antimalarial principle. The physicochemical properties of the alkaloid were consistent with the proposed structure of dehatrine (1). However, the alkaloid isolated by us was shown to be a mixture of two rotational isomers. The X-ray crystallographic analysis of 1 has shown that two rotamers are incorporated in a single crystal 1:1 ratio. The complex NMR spectrum of 1 has also been defined as a mixture of two rotamers by extensive use of 2D (COSY and COLOC) techniques. Dehatrine (1) has been shown to significantly inhibit the growth of cultured Plasmodium falciparum K1 strain (chloroquine resistant) with similar activity to quinine.