16531-04-7

Basic information

• Product Name: 1',2'-Didehydro-7',10,11-trimethoxyemetan-6',9-diol
• Synonyms: 1',2'-Didehydro-7',10,11-trimethoxyemetan-6',9-diol;Alangicine
• CAS NO: 16531-04-7
• Molecular Formula: C₂₈H₃₆N₂O₅
• Molecular Weight: 480.59584
• Mol File: 16531-04-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 675.3°Cat760mmHg
• Flash Point: 362.2°C
• Appearance: /
• Density: 1.26g/cm³
• CAS DataBase Reference: 1',2'-Didehydro-7',10,11-trimethoxyemetan-6',9-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1',2'-Didehydro-7',10,11-trimethoxyemetan-6',9-diol(16531-04-7)
• EPA Substance Registry System: 1',2'-Didehydro-7',10,11-trimethoxyemetan-6',9-diol(16531-04-7)

Safety Data

• Hazardous Substances Data: 16531-04-7(Hazardous Substances Data)

Usage

Definition

ChEBI: An isoquinoline alkaloid that is 1',2'-didehydroemetan bearing two hydroxy substituents at positions 6' and 9 as well as three methoxy substituents at positions 7', 10 and 11.

Upstream product

• 61194-41-0 (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetic acid 
• 61194-42-1 (+/-)-8-benzyloxy-N-(3-benzyloxy-4-methoxyphenethyl)-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetamide 
• 56774-72-2 ethyl (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetate 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 61194-43-2 (+/-)-8-benzyloxy-2β-(6-benzyloxy-3,4-dihydro-7-methoxy-1-isoquinolyl)methyl-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine 
• 61194-41-0 (2R,3R,11bS)-(-)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetic acid 
• 57130-35-5 (2R,3R,11bS)-(-)-8-(Benzyloxy)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetic Acid Ethyl Ester 
• 61194-42-1 (2R,3R,11bS)-(-)-8-benzyloxy-N-(3-benzyloxy-4-methoxyphenethyl)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetamide 

Relevant articles and documents

Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine: Syntheses of (+/-)- and (+)-Alangicines

The first total synthesis of alangicine (3), an Alangium lamarckii alkaloid, has been achieved in the form of a racemic modification by means of an initial alkaline hydrolysis of the (+/-)-tricyclic ester 6 and succeeding steps proceeding through the intermediates (+/-)-7, (+/-)-10, and (+/-)-9.A parallel synthetic route starting with the (-)-tricyclic ester 6, derived from (+)-cincholoipon ethyl ester (8), produced the chiral target molecule (+)-3 via the intermediates (-)-7, (-)-10, and 9.The identity of the synthetic (+)-3 with alangicine unequivocally established the structure and absolute stereochemistry of this alkaloid.The (13)C nuclear magnetic resonance spectra of (+/-)-alangicine (3) and the ipecac and Alangium alkaloid psychotrine (18) confirmed their endocyclic double bond structures in the dihydroisoquinoline moiety.Catalytic reductions of 11, (+/-)-12, and 15 using hydrogen and Pd-C were investigated, and the results have shown that hydrogenolysis of the benzyloxy group proceeds much faster than saturation of the endocyclic C=N bond.Keywords - alangicine; psychotrine; structure; absolute configuration; stereoselective synthesis; (13)C NMR; CD; benzyl ether; hydrogenolysis