Isocorynantheidine

Base Information

• Chemical Name: Isocorynantheidine
• CAS No.: 7729-22-8
• Molecular Formula: C₂₂H₂₈N₂O₃
• Molecular Weight: 368.476
• UNII: 2CB4G689XT
• Nikkaji Number: J146.158C
• Wikidata: Q104399101
• Mol file: 7729-22-8.mol

Synonyms:Isocorynantheidine;3-Isocorynantheidine;2CB4G689XT;7729-22-8;17,18-Seco-3.beta.,20.alpha.-yohimban-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (E)-;Corynan-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (3.beta.,16E,20.beta.)-;UNII-2CB4G689XT;17,18-Seco-3beta,20alpha-yohimban-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (E)-;Corynan-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (3beta,16E,20beta)-;INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3S,12BR)-;INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (2S-(2.ALPHA.(E),3.ALPHA.,12B.ALPHA.))-;Indolo(2,3-a)quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (2S-(2alpha(E),3alpha,12balpha))-;Indolo(2,3-a)quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphaE,2S,3S,12bR)-

Chemical Property of Isocorynantheidine

Chemical Property:

• PSA: 54.56000
• LogP: 3.75440
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 368.20999276
• Heavy Atom Count: 27
• Complexity: 578

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=CC=CC=C34
• Isomeric SMILES: CC[C@@H]1CN2CCC3=C([C@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=CC=CC=C34

Technology Process of Isocorynantheidine

There total 36 articles about Isocorynantheidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

methanol (67-56-1) + 2-((2R,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-oxo-propionic acid methyl ester (26076-15-3,61246-74-0,75991-86-5,76376-59-5) → (+/-)-hirsutine (4684-43-9,4925-50-2,7729-22-8,7729-23-9,7762-19-8,14509-88-7,23407-35-4,50439-68-4,76376-57-3)

Guidance literature:

With hydrogenchloride; In dichloromethane; at -20 ℃; for 72h;

DOI:10.1021/ja00547a041

Reference yield: 50.0%

(+/-)-Z-geissoschizine methyl ether → (+/-)-corynantheidine (4684-43-9,4925-50-2,7729-22-8,7729-23-9,7762-19-8,14509-88-7,23407-35-4,50439-68-4,76376-57-3)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol; for 1h;

DOI:10.1016/0040-4039(95)01794-I

Reference yield: 36.0%

(+/-)-3-epi-Z-geissoschizine methyl ether → (+/-)-hirsutine (4684-43-9,4925-50-2,7729-22-8,7729-23-9,7762-19-8,14509-88-7,23407-35-4,50439-68-4,76376-57-3) + (+/-)-3-isocorynantheidine

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol; for 1h;

DOI:10.3987/COM-98-S9

upstream raw materials:

diazomethane

dimethyl sulfate

methanol

2-((2R,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-oxo-propionic acid methyl ester

Refernces

• 1、 Lounasmaa, Mauri,Jokela, Reija,Laine, Christiane,Hanhinen, Pirjo. "Preparation of (±)-hirsutine and (±)-3-isocorynantheidine". . p. 445 - 450. Retrieved 2007/10/03.
• 2、 Brown, Richard T.,Jones, Martin F.,Wingfield, Mark. "Stereoselective Total Synthesis of (+/-)-Hirsutine and Related Corynanthe Alkaloids". . p. 847 - 848. Retrieved 2007/10/02.