(+)-3-[(1S)-3β-Ethenyl-2β-isocyano-3-methyl-6α-(1-methylethenyl)cyclohexane-1β-yl]-1H-indole

Base Information

• Chemical Name: (+)-3-[(1S)-3β-Ethenyl-2β-isocyano-3-methyl-6α-(1-methylethenyl)cyclohexane-1β-yl]-1H-indole
• CAS No.: 101968-71-2
• Molecular Formula: C21H24 N2
• Molecular Weight: 304.435
• Mol file: 101968-71-2.mol

Synonyms:1H-Indole,3-[3-ethenyl-2-isocyano-3-methyl-6-(1-methylethenyl)cyclohexyl]-, [1S-(1a,2a,3a,6b)]-; (+)-Hapalindole C;Hapalindole C

Chemical Property of (+)-3-[(1S)-3β-Ethenyl-2β-isocyano-3-methyl-6α-(1-methylethenyl)cyclohexane-1β-yl]-1H-indole

Chemical Property:

• PSA: 28.15000
• LogP: 5.25310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-3-[(1S)-3β-Ethenyl-2β-isocyano-3-methyl-6α-(1-methylethenyl)cyclohexane-1β-yl]-1H-indole

There total 1 articles about (+)-3-[(1S)-3β-Ethenyl-2β-isocyano-3-methyl-6α-(1-methylethenyl)cyclohexane-1β-yl]-1H-indole 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:

geranyl diphosphate (763-10-0) + (Z)-2-(3-Indolyl)vinyl Isocyanide (61168-06-7) → hapalindole C (101968-71-2) + (-)-hapalindole U

Guidance literature:

With Stig cyclase FamD₂; stig cyclase WepC₁ cloned from Westiellopsis prolifica SAG 16.93 genomic DNA; stig cyclase WepC₂ cloned from Westiellopsis prolifica SAG 16.93 genomic DNA; calcium chloride; magnesium chloride; In aq. buffer; at 30 ℃; pH=7.8; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/anie.201913686

Reference yield:

hapalindole C (101968-71-2) → N-[(1R,2R,5S,6S)-6-(1H-Indol-3-yl)-5-isopropenyl-2-methyl-2-vinyl-cyclohexyl]-formamide (117184-36-8) + (1S,4R,4aR,11cS)-1-Isopropenyl-4-methyl-4-vinyl-2,3,4,4a,7,11c-hexahydro-1H-indolo[2,3-c]quinoline (117184-37-9)

Guidance literature:

With formic acid; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jo00260a014

upstream raw materials:

geranyl diphosphate

(Z)-2-(3-Indolyl)vinyl Isocyanide

Downstream raw materials:

N-[(1R,2R,5S,6S)-6-(1H-Indol-3-yl)-5-isopropenyl-2-methyl-2-vinyl-cyclohexyl]-formamide

(1S,4R,4aR,11cS)-1-Isopropenyl-4-methyl-4-vinyl-2,3,4,4a,7,11c-hexahydro-1H-indolo[2,3-c]quinoline

Refernces